Vacation rentals in Siena, Italy with a pool

Explore 229 vacation rentals, homes, and villas with pools in Siena for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Pet-Friendly Homes. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $61 per night and homes offering up to 31 bedrooms and 28 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

229 Homes with Pools in Siena

Superior Smart Villa Surrounded by Green Hills

Siena, IT
4 Bedrooms 8 Guests
Aug 23 - 28
$2,463 night

The Price includes: - Utilities: water, gas for kitchen use, weekly linen, initial and final cleaning, for stays of at least 7 nights, internal reorganization midweek (on Wednesday) with cleaning the bathrooms, tidying up the bedrooms and kitchen with change of bath towels, park and pool maintenance, wireless Internet connection - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage caused to the property during your stay (up to the ceiling of 1,500.00€ and with the restrictions provided). The Price does not Include: - Mandatory extra cleaning in case of animals (€ 7,15/day/animal) - tourism tax (€ 2,00 per person per day for the first 4 days. Please note that children under 12 years old will not pay) Just three kilometers from the historic center of Siena, La Fonte di Santa Regina is a true corner of paradise nestled in the Tuscan countryside. Set atop a scenic hill and surrounded by rolling landscapes of vineyards, olive groves, and cultivated fields, the property offers breathtaking views stretching from Monte Amiata to the Torre del Mangia. At its heart stands an ancient farmhouse, now transformed into an elegant luxury residence. Exposed stone, wood, and contemporary materials create a refined balance between tradition and minimalist design. Spacious, light-filled interiors feature bedrooms with en-suite bathrooms and carefully curated furnishings, all designed to provide the highest level of comfort. The villa is fully equipped with high-speed Wi-Fi, air conditioning throughout, and smart home technology—ideal for a truly exclusive stay. Within the estate grounds, a separate building houses a large event hall suitable for conferences, ceremonies, and private gatherings, complete with a professional kitchen (available on request), as well as a wellness area with sauna and hot tub. The beautifully maintained park includes several relaxation areas, a stunning infinity pool, and sweeping views over Siena. A perfect retreat to unwind in nature’s rhythm, yet just a short drive from Tuscany’s most iconic destinations: Val d’Orcia, Val di Chiana, the Crete Senesi, Chianti, and the timeless villages of Montalcino, Pienza, San Gimignano, and Montepulciano. Please Note: when the property is rented in this solution no other guests will be present on site. Starting in 2026, the first floor of the villa, with an adjacent private entrance, will be occupied by the owners, a young couple who are generally away for work but available if needed. They will share only the driveway and parking area with guests, while the park and swimming pool will remain for the exclusive use of the guests. THE PROPERTY HAS BEEN SUBJECTED TO A CHECK-UP BY A TECHNICAL RESPONSIBLE TO ENSURE CONSISTENCY OF THE DESCRIPTION, ACCESSORIES LISTED ON THIS PAGE AND THEIR PRESENT STATE OF OPERATION/MAINTENANCE Interior: The complex consists of two structures: the main house and an annex located a few metres away, near the pool. MAIN HOUSE: in the house on two levels, the main entrance leads into an open-plan area with living room, dining table and kitchen. The ground floor is completed by a double bedroom with private bathroom with shower and the laundry room. A staircase in glass and iron leads up to the top floor with three double bedrooms with private bathroom with shower. The laundry room is available to both units. ANNEX: two large doors open into a spacious room suitable for events, conferences and business meetings (with guest bathroom), then from here a few steps lead to a equipped kitchen with central island. These rooms are available on request (at an extra cost). On the lower level of the annex, reached from the pool area via a flight of steps or, alternatively, from the house across the garden, is a wellness area with heated whirlpool tub, sauna and a bathroom with shower. Park: Thirty hectares of land delimit the immense spaces of this modern farm estate, with alternating olive trees, vineyard and woodland, fenced for about 12 hectares (by electro welded mesh height 1.80 m) leand for the most part passable on foot and suitable for playing games. A splendid, expertly-designed park of about 1500 sq m surrounds the house: between winding paths, bordered by wavy flowering bushes of herbs, which lead to the two ground floor entrances to the house, are large areas of manicured lawn, reinvigorated by young olive and cypress trees and, again, many bushes of lavender, rosemary, myrtle and sage adorning the walkways that lead to the set-up areas: the two gazebos (located on either side of the house in a panoramic position), a delightful seating area located at the entrance of the pool area, a children’s play area and ping-pong table, a wood oven, barbecue area and the pool area provide guests with wonderful moments of relaxation and fun with the complicity of fascinating panoramic views from every part of the park. The property has an automatic access gate and a large parking area, located at the end of the short internal driveway, just a few steps from the entrances to the house. Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens’ grass could be different at the moment of your arrival at the villa. Swimming Pool: A few steps across the garden and a short flight of steps (as an alternative to the paved walkway) go from the house to the pool area: a natural scenic terrace, embellished by the rows of olive trees and vineyards of the property that stretch as far as the eye can see to the peaks of Mount Amiata and the Torre del Mangia. In the centre lies the beautiful, south-facing infinity pool, perfect for sitting out at sunset or at night, when a clever play of lighting inside and outside the pool creates a magical atmosphere. The pool is edged with travertine slabs and lined in PVC in an innovative design inspired by the natural element of marble, conferring a unique and iridescent character, based on the natural light of the sun. It measures 5 x 15 m with the depth varying from 1.20 to 1.40 m. A ramp of submerged steps facilitates entry. A cold and hot-water shower is located in a corner of the area and there is a chlorine purification system. Comfortable seats and the sitting area, shaded by large umbrellas, are the perfect complement to the solarium, which is enhanced by a dining area with large table, sink and barbecue, guaranteeing full relaxation in the open air. The pool is available to guests from the last Saturday of April until the first Saturday of October. Extra On Request: Use of external pool’s kitchen with extra cost of € 500,00 per week or part of week, use of external pool’s kitchen and multipurpose room (€ 1.500,00 for one week or part of week, € 2.000,00 for two weeks, € 2.500,00 for three weeks and € 3.000,00 for four weeks) extra cleaning (601.00 euros per day), extra linen (16 euros per person), heating (on consumption up to date market prices), firewood (€32.00 per box - 15/20 Kg) Property Registration Number: 052032AAT0074

Villa Essence of Tuscany with Pool, Garden, Siena View

Siena, IT
5 Bedrooms 11 Guests
Aug 27 - 30
$2,055 night

Nestled in the greenery of the Tuscan countryside with a breathtaking view of the Siena hills up to the Val d’Orcia and Mount Amiata, this typical Tuscan Villa is a magnificent property consisting of 5 rooms and 5 bathrooms, that can accommodate large groups of guests of up to 11 people. Our typical Tuscan Villa can be found just a few kilometers from the charming city of Siena. The Villa offers a splendid garden, an exclusive pool with a sunbathing and solarium area with comfortable loungers, as well as a large and spacious outdoor cover terrace perfect for Al Fresco dining, WiFi and air conditioning. Bedroom 1: • 2 Queen-size Beds with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 2: • Double-size Bed with Fresh Sheets and Pillowcases • External Bathroom with Shower, Bathtub , Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 3: • Queen-size Bed with Fresh Sheets and Pillowcases • 2 Single Beds with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 4: • 2 Single Beds with Fresh Sheets and Pillowcases • External Bathroom with Shower, Bathtub , Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 5: • Double-size Bed with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access The villa’s interiors are very bright and large with typical and authentic Tuscan furnishings arranged across the ground and first floor. Living & Dining Room The living and dining room are provided with sofas, armchairs, a dining table that can accommodate up to 12 people. There are many windows that let in natural light. There is also a billiard room, with foosball table and ping pong Al fresco dining External to the property you will find another table for al fresco dining with seats up to 12 people Terrace There’s direct access to a private covered terrace with large dining table for 12 Kitchen The spacious and fully equipped kitchen includes everything you need to prepare an unforgettable Italian dinner, including an oven, fridge and freezer, coffee maker, tea kettle, dishwasher, washing machine and toaster. There is also a table with chairs with 8 seats. A dream villa for families and groups of friends seeking nature, tranquility and authenticity License number: IT052032B5RS8F8TNP

Terra di Siena 12 Emma Villas

Castelnuovo Berardenga, IT
7 Bedrooms 14 Guests
Sep 4 - 8
$3,695 night

The rate includes: - Utilities: electricity - water - gas for kitchen use and hot water - weekly linen, initial and final cleaning - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage caused to the property during your stay (up to the maximum of 1,500.00€ and with the restrictions provided). The rate does not include: Mandatory extra cleaning in case of the presence of animals (€100.00 per animal per week or part of the week and only small pets ). Tourist tax (€2.00 per person per day for the first 7 days). Children under 14 are exempt) Terra di Siena is a 15th-century rural retreat surrounded by vineyards, olive groves, and cypresses, within easy reach of Siena. Originally built as a monastery and later used as a farmhouse, the villa has been expertly restored and equipped to blend historic charm with modern comfort, sport, and music. The farmhouse is arranged around a large internal courtyard. Original features such as exposed stone walls, terracotta floors, timber beams and restored antique furnishings are complemented by a music room, billiards room, gym, wine tasting room and modern kitchen. The property sleeps up to fourteen guests across seven bedrooms (in the full version), all with en-suite or private bathrooms. A large garden with panoramic dining terraces, a pool and a private tennis court sets the scene for leisurely days and activity together outside. Ideal for active guests, there is also a table tennis table, a football goal and a basketball hoop. The location is perfect for exploring the Chianti region and its nearby towns and castles, with Siena, San Gimignano and the vineyards of Gaiole and Radda within easy reach. THE PROPERTY HAS UNDERGONE A CHECK-UP CARRIED OUT BY ONE OF OUR TECHNICAL MANAGERS, TO GUARANTEE THE CORRESPONDENCE OF THE DESCRIPTION, THE ACCESSORIES LISTED ON THE SITE AND THEIR STATE OF OPERATION/MAINTENANCE. Interiors: The complex consists of the main house and an annex in the pool area. FARMHOUSE (on three levels). FIRST FLOOR — Main entrance through a covered porch on the hallway: on one side, dining room and kitchen; on the other, sitting area and study corner; a double bedroom with en suite bathroom with bathtub; a double bedroom with external access and en suite bathroom with shower. SECOND FLOOR — A double bedroom with en suite bathroom with shower; a master bedroom with walk-in closet and en suite bathroom with shower; music room. Going down a few steps: living room (with external access and ornamental fireplace); a double bedroom; a bathroom with shower and laundry area with washing machine and dryer; a double bedroom with en suite bathroom with tub and shower. GROUND FLOOR - Billiard room; a bathroom with shower (also accessible from the pool area and the internal staircase). With independent access to the back of the building there is the gym; a wine tasting room; an additional laundry room and the outdoor kitchen that accesses the porch equipped with a dining area and barbecue. ANNEX - Living area with mini fridge; a double bedroom (also with independent access) with living room and kitchenette and an en suite bathroom with shower. Park: The property covers about 2.5 hectares and is completely fenced. It includes olive groves, vineyards, fruit trees, a small wooded area and bay and jasmine hedges. The central courtyard, enclosed by the villa’s buildings, is enriched with ornamental plants, climbing bougainvilleas and shaded areas equipped with seating. On the south side of the villa, a covered porch is furnished with a table and a relaxation area for eating and relaxing outdoors. A paved terrace with table and chairs is located in front of the pool. On the side of the villa there is a table tennis table. Stone paths cross oak and oak groves until you reach the private tennis court, also equipped with a basketball hoop and soccer goal. Access is via a gravel driveway with parking near a large oak tree that gives its name to the villa’s courtyard. N.B.: Please note that photo shoots are usually carried out in spring, so the colors and blooms of the gardens, lawns and parks may be different when you enter the villa. Pool: The swimming pool is located a few steps from the villa, partially screened by a laurel hedge. Rectangular in shape; measures 13.4 x 4.5 m with a depth ranging from 1 to 2 m; lined in porcelain stoneware; accessed via Roman steps; chlorine purification system; internal lighting. The surrounding solarium is furnished with sunbeds, umbrellas and a solar shower. A nearby pool house includes a bathroom with shower and a mini fridge. The pool is open from mid-April until mid-October and and can be heated on request (service available at no extra cost and with prior notice). Tennis Court: The tennis court is located 50 m from the villa; synthetic grass ground; fenced; rackets available. The area is also equipped with a basketball hoop with a scoreboard and net, and a soccer goal with a net. On Request: extra cleaning (€ 25,00/hour per cleaner - minimum 2 hours) extra linen (€ 12,00 per person) Heating from November to April (€ 40,00 per day). N.B. These costs, not included in the price list, will be calculated at the reservation time and due at the balance payment. Property Registration Number: 052006LTN0153

Finestra Su Siena 16

Siena, IT
8 Bedrooms 16 Guests
Aug 23 - 28
$2,307 night

The Price includes: - Utilities: electricity - water - gas for kitchen use - weekly linen, initial and final cleaning - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage to the property during your stay (up to the maximum of € 1,500.00 and with the limitations provided). The Price does not Include: - Mandatory extra cleaning in case of animals (€ 50,00/week or part of week/animal) - Tourist Tax (where applicable) Less than 10 km from the historic center of the most Gothic city in Tuscany, a unique condensation of artistic and architectural, environmental, cultural and gastronomic wonders, we find Finestra su Siena, an ancient restored stone farmhouse which is distributed over four levels to comfortably accommodate up to 16 people. To complete the picture, a park and a swimming pool for exclusive use and a splendid view that crosses the rolling green hills studded with vines and olive trees and frames the profiles of the city of Siena: a perfect context for having all the most coveted destinations that dot the medieval city of the Palio: the Valli dell’Orcia, della Chiana, the Crete Senesi, the Chianti and the unmissable villages of eternal charm such as Montalcino, Pienza, San Gimignano, Montepulciano, all reachable in modest times through splendid panoramic roads bordered by soaring cypresses and enchanted landscapes. Well connected to the main expressways to reach tourist destinations and airports, it is a short walk from the railway station and the major shopping centers of the city (7km). Interior: The house has four levels covering an area of about 450 sq m. On the ground floor a large French window leads into the living area with sofa and dining table. This area leads to two double bedrooms (with direct access to the outside via a French window) that share a bathroom with shower and a sitting room and connected with the kitchen and with a double bedroom with joinable beds and ensuite bathroom with shower. This floor is served by a further bathroom with shower with access from the kitchen. From the living room staircases lead up to the next floor and down to the basement where is located the laundry room. On the first floor, accessible directly from the outside as well via a stone staircase, is a a sitting room (with panoramic balcony), a large kitchen, two double bedrooms with ensuite bathroom with shower and a twin bedroom (with joinable beds) served by a bathroom with shower. The top floor consists of the attic, composed of a large open-plan living room, a double bedroom served by a bathroom with shower and a twin bedroom (with joinable beds) with private bathroom with shower and tub. Air conditioning in the bedrooms. Park: The 2000 sq m park surrounding the villa is covered mainly in lawn and bordered along the perimeter by a mixed-hedge screen. From the entrance gate to the property, a short drive passes in front of the main entrance, where you can unload your luggage, and then leads to a private 6-car parking area. The pergola furnished with table and chairs is just outside the kitchen French window and next to the pool.Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens’ grass could be different at the moment of your arrival at the villa. Swimming Pool: The swimming pool is accessible from the entrances of the farmhouse by walking just a few steps across the lawn. Bordered on the sides by a discreet hedge, it is framed by a sunbathing area equipped with loungers and umbrellas; Rectangular in shape and lined internally with PVC; it , features submerged steps; Measures are 5 x 10 meters, with a depth ranging from 1.40 to 2.20 meters; filtration system with chlorine. Open from the last Saturday in April until the first Saturday in October. Extra On Request: - extra cleaning (€ 22,00/hour per cleaner) - extra linen (€ 15,00 per person) Property Registration Number: 052032LTN1185

Villa Majestic Tuscany with Infinity Pool & Lush Garden

Siena, IT
6 Bedrooms 12 Guests
Sep 7 - 10
$1,632 night

Nestled in the greenery of the Tuscan countryside with a breathtaking view of the Siena hills up to the Val d’Orcia and Mount Amiata, this typical Tuscan Villa is a magnificent property consisting of 5 rooms and 5 bathrooms, that can accommodate large groups of guests of up to 11 people. Our typical Tuscan Villa can be found just a few kilometers from the charming city of Siena. The Villa offers a splendid garden, an exclusive pool with a sunbathing and solarium area with comfortable loungers, as well as a large and spacious outdoor cover terrace perfect for Al Fresco dining, WiFi and air conditioning. Bedroom 1: • King-size Bed with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Bathtub, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 2: • 2 Queen-size Beds with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Bathtub, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 3: • 1 Double-size Bed with Fresh Sheets and Pillowcases • 1 Single Bed with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 4: • Single Bed with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 5: • Double-size Bed with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 6: • 2 Single Beds with Fresh Sheets and Pillowcases • En-suite Bathroom with Shower, Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access The villa’s interiors are very bright and large with typical and authentic Tuscan furnishings arranged across the ground and first floor. Living & Dining Room The living and dining room are provided with sofas, armchairs, a dining table that can accommodate up to 12 people. There are many windows that let in natural light, and a foosball table. Al fresco dining External to the property you will find another table for al fresco dining with seats up to 14 people. There is also an area with ping pong table Terrace There’s direct access to a private covered terrace with sofa and armchairs, amd a little table to enjoy a breakfast with view Kitchen The spacious and fully equipped kitchen includes everything you need to prepare an unforgettable Italian dinner, including an oven, fridge and freezer, coffee maker, tea kettle, dishwasher, washing machine and toaster. There is also a table with chairs with 8 seats. A dream villa for families and groups of friends seeking nature, tranquility and authenticity License number: IT052032B5RS8F8TNP

Medieval Castle Living: Vineyards, Swimming Pool & Rustic Tuscan Charm

Sovicille, Tuscany, IT
6 Bedrooms 12 Guests
Aug 23 - 25
$2,568 night

Welcome to a beautifully preserved 13th-century Tuscan estate, where history, landscape and authentic hospitality come together. The property is part of a small castle estate with independent guest residences. The owners live in the castle’s main building, while four elegant guest apartments are located in the surrounding historic buildings. Each apartment features its own private entrance and fully equipped kitchen, creating an ideal setting for couples or families travelling together who appreciate both privacy and the atmosphere of a historic estate. Here you are invited to experience life within a historic castle property hosted by its owners, Sveva and her husband Marco, a prominent Sienese lawyer who have carefully restored the estate and its surrounding vineyards over the years. As the vineyard has grown and flourished, they recently chose to partner with Best of MAS to assist with welcoming guests and managing stays, allowing them to continue dedicating their time to the estate and its wines. Throughout the property, the character of centuries past has been lovingly preserved: original terracotta floors, thick stone walls, antique furnishings and open views across vineyards and countryside create a setting that feels timeless and deeply rooted in Tuscany. Mornings begin with a gourmet breakfast prepared by Sveva and served in the castle’s grand hall: a beautiful historic space that guests may also reserve for special dinners upon request. During your stay, you are also invited to visit the estate’s ancient wine cellars and enjoy a tasting of the wines produced directly on the property from the owners’ Super Tuscan selection. Outside, the gardens open onto the rolling landscapes of the Montagnola Senese. A generous 20-metre swimming pool is set among vineyards and cypress trees, offering a peaceful place to relax and enjoy long Tuscan afternoons under the sun. The estate is located just fifteen minutes from the historic centre of Siena and two kilometres from the charming village of Sovicille, where you will find local restaurants and a small grocery shop. From here, the celebrated towns of Florence, San Gimignano, Arezzo and Volterra are all easily reached for memorable day trips. The castle estate comfortably accommodates up to twelve guests across the four apartments, with the possibility of hosting two additional guests upon request. INCLUDED IN YOUR STAY Farm-to-Table Castle Breakfast Each morning begins with a freshly prepared breakfast served in the castle’s elegant common grand hall, featuring organic and locally sourced ingredients. The Grand Hall may also be reserved upon request for private lunches or dinners. Private Cellar Visit and Wine Tasting Guests are invited to explore the estate’s historic wine cellars and enjoy a tasting of the wines produced on the surrounding vineyards. THE SWIMMING POOL The 20-metre private pool is open from 15 May to 30 September. Daily cleaning is performed by the castle staff. We kindly ask guests to use the pool with care and respect to preserve its beauty. PARKING Private parking is always available on-site, free of charge. The guest accommodations are divided into four independent apartments, each featuring its own private entrance and fully equipped kitchen. To ensure total privacy and atmosphere, the apartments are rented exclusively to your group, comfortably accommodating up to twelve guests. GROUND FLOOR RESIDENCES: Two enchanting apartments open directly onto the gardens, surrounded by aromatic herbs, vines, and the lush greenery of the estate, an ideal setting for those who wish to step straight into the Tuscan countryside. The first apartment features a double bedroom with an en-suite bathroom and a living area with a cozy fireplace. The second apartment offers two double bedrooms, two bathrooms, and a living room with a fireplace. COMFORT: Air conditioning is available in both ground-floor residences. FIRST FLOOR APARTMENTS: Accessed by a stone staircase, the two upper apartments feature historic furnishings dating back centuries and elevated views across the vineyards and rolling hills. - "Archi" Apartment: Comprises a double bedroom and a bathroom; an additional twin bedroom (with two single beds) can be made available upon request. - "Vigne" Apartment: Features two bedrooms (one double and one with two single beds, which cannot be joined) and two bathrooms. Both apartments include a private living area and a fully equipped kitchen. All apartments are equipped with air conditioning in the bedrooms, in the rest of the apartments, the thick medieval stone walls naturally regulate the interior temperature, keeping the rooms pleasantly cool even during the Tuscan summer. Windows are fitted with insect screens to allow the fresh countryside breeze to circulate, while high-quality fans are provided for additional comfort. OPTIONAL GUEST EXPERIENCES For those wishing to immerse themselves more deeply in the Tuscan lifestyle, a selection of curated experiences can be arranged: - Dinner with the Castellana: an elegant, candlelit dinner hosted in the atmospheric castle courtyard and prepared by the Lady of the Castle Sveva. - Private cooking classes or professionally catered dinners available upon request such as guided visits to local wineries, bike excursions, or scenic walks through the Montagnola Senese. - Truffle Hunting: An authentic countryside adventure led by local experts and their trained dogs.

Stunning Rustic Villa with Tranquil Sun Soaked Pool

Sovicille, IT
3 Bedrooms 8 Guests
Sep 8 - 12
$1,063 night

The Price includes: - Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage to the property during your stay (up to the maximum of € 1,500.00 and with the limitations provided). The Price does not Include: Mandatory extra cleaning in case of animals (€ 50,00/week or part of week/animal) Tourism tax (€ 1,50 per person per day for the first 12 days. Please note that children under 12 years old will not pay). La Capanna di Franca is an old barn which, in 2006, thanks to careful restoration work that has enhanced the original architectural style, was transformed into a warm and comfortable country house. Standing in the medieval hamlet of Palazzavelli, a tiny cluster of houses just one kilometre from the centre of Sovicille, but in an independent position, this rustic stone farmhouse is surrounded by a lush garden with a beautiful view from the windows of the first floor over the surrounding countryside against the background of Siena which is just a few kilometres away. Immersed in the natural oasis of the Montagnola Senese which is rich with the evidence of an ancient past marked by the passage of great civilizations, it is the perfect setting for fans of unspoiled nature who can explore it, directly from the property, either walking, mountain biking or horseback riding along the trails in the woods. Its geographical position makes it a perfect departure point for discovering the art masterpieces and the fine food and wine specialities in the most suggestive villages of the area, such as Montepulciano, Pienza, Montalcino and the picturesque hamlets of Chianti. The highway, a few kilometres away, leads you easily to Cortona, San Gimignano and other important Tuscan art cities such as Florence, Lucca and Pisa. Interior: The house has two floors. The entrance on the ground floor leads directly into a spacious, open-plan living area composed of a lounge with a large fireplace, dining area and kitchen. This floor includes a study with single sofa bed, a bathroom with shower and the laundry. A travertine and wrought-iron staircase in the living room leads up to the first floor consisting of two double bedrooms, one with ensuite bathroom with shower, a double bedroom with extra single bed and a bathroom with whirlpool tub. A flight of stairs leads up to a loft area with a super panoramic window and fitted out with gym equipment. Air conditioning (except in a double bedroom equipped with ceiling fan). Park: The park around the house covers an area of about 5000 square metres, mainly lawn. From the entrance gate of the property a driveway bordered by rows of cypresses takes guests through the well-kept, blooming garden with typical plants such as cork and holm oaks, mulberry and olive trees alternating with palms and pomegranates. Bushes of rose and broom colour the many shades of green while beds of seasonal flowers border the stone path that leads to the pool. The atmosphere is quiet and reserved and entices one to spend time outdoors and to organize pleasant meals under the large porch, furnished with table and chairs, right outside the living room French window. Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens’ grass could be different at the moment of your arrival at the villa. Swimming Pool: The infinity pool is immersed in the beautiful garden just 15 m from the house. Bordered along one side by a discreet hedge, it is framed by fragrant roses and surrounded by a carpet of well-kept lawn where the sunbathing area has been set up with sunbeds, awning and a hammock. The rectangular-shaped pool, with border in Tuscan travertine and internally lined with mosaic tiles, has large steps for access to the water. It measures 6 x 12 m with a varying depth of 1,20 m to 2,20 m. and has chlorine purification. There is an outdoor shower and lighting both inside and outside the pool. Finally, completing the area, is a wooden gazebo with table and chairs. The pool is open from the last Saturday in April to the first Saturday in October. Pets: Yes. € 50,00 per animal per week or part of week. Extra On Request: - Extra cleaning (€ 22,00/hour per cleaner), - extra linen (€ 15,00 per person), - heating (on consumption up to date market prices), - firewood (€ 20,00/100 Kg) Property Registration Number: 052034LTN0053

Treccianino 12

Siena, IT
6 Bedrooms 12 Guests
Aug 29 - Sep 5
$936 night

Treccanino 12 is an elegant and spacious holiday home in Tuscany, perfectly suited for a luxurious getaway with family or friends. The property accommodates up to twelve guests and impresses with its vast garden, manicured lawns, terracotta planters, blooming flowers and decorative shrubs. The large pool offers a refreshing escape, while the stunning views over the rolling hills and vineyards of the Val di Merse complete the idyllic setting. The house is located south-west of Siena, close to Chianti and val d’Orcia, just two kilometres from the charming village of Sovicille, where you can find a restaurant and a small grocery shop. For larger shopping trips, there is a Coop supermarket in nearby Rosia, only six kilometres away. The Tenuta di Treccianino winery is also just a short walk away. The historic city of Siena is about a 30-minute drive, and day trips to San Gimignano, Florence, Arezzo or Volterra are easily arranged. Treccanino 12 consists of a two-storey main house and a separate cottage with its own bedroom, bathroom and living, dining and kitchen area. This extra building offers an ideal retreat for couples or guests who value added privacy. Several covered outdoor terraces with dining tables, a fully equipped outdoor kitchen with grill and pizza oven, and the generous pool area ensure plenty of space for relaxation and shared moments. Inside, the house features a tasteful mix of traditional Tuscan charm, wooden beam ceilings, exposed stone walls, fine marble details and parquet floors. The elegant yet cosy furnishings create a welcoming atmosphere where guests will immediately feel at home. Treccanino 12 combines comfort, luxury and authentic Tuscan character for an unforgettable holiday experience. Ground Floor Hall Stairs to first floor, main entrance, door to external laundry room Lounge Two sofas, fireplace, TV, doors to terrace Dining Room 1 Table and chairs, cupboard, door to garage Dining Room 2 Table and chairs, sideboard, French doors to terrace. Kitchen Fully equipped, breakfast bar with chairs, doors to garden, door to utility room Utility Room Fridge-freezer, sink, washing machine Cloakroom Sink, WC. First Floor Hallway Desk and chair. Bedroom 1 Twin beds (cannot be converted to double), wardrobe, armchair. Bedroom 2 Double bed (can be converted to twins), drawers, shelves, wardrobe. En-suite Bathroom Shower, sink, WC, bidet Bedroom 3 Double bed (can be converted to twins), shelves, chair. En-suite Bathroom Jacuzzi bath with shower, sink, WC, bidet Bedroom 4 Double bed (cannot be converted to twins), walk-in wardrobe, armchair, table. En-suite Bathroom Shower, sink, washstand, WC, bidet Bathroom Shower, sink, WC, bidet Apartment Studio Kitchenette, double bed (cannot be converted to twins), table with chairs, sofa, shelves, TV En-suite Bathroom Shower, sink, WC, bidet Cottage Lounge-kitchen-diner Kitchenette, table with chairs, two cupboards, sideboard, sofa, media unit, doors to pool area. Bedroom Double bed (cannot be converted to twins), wardrobe. Bathroom Shower, sink, cupboard, WC, bidet Private Pool: Length: 13 metres Width: 5.5 metres Depth: 1.4 -2.8 metres Entrance: Metal ladder Opening times: May to October, weather permitting Fenced: No Furnished: Sun loungers and parasols, Shower and WC, BBQ area. A pavilion furnished with armchairs and a sofa is just a few steps away. Cleansed: Chlorine there are 2-3 parking spaces in the garage and also many uncovered spaces on the property. Local charges Tourist tax: 1.50 € per person, per night for the first 6 nights, some exemptions apply Charged based on usage: Heating Villa Children: This villa is suitable for children aged 6 and above only Arrival guide Approach road: Paved Parking: Private, onsite parking

Villa Rinaldi 6 in Carpineta

Carpineta, IT
3 Bedrooms 6 Guests
Aug 23 - 30
$855 night

This rate includes: - Utilities: water - gas for kitchen use and hot water - Weekly linen, initial and final cleaning - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage to the property during your stay (up to the maximum of € 1,500.00 and with the limitations provided). The price does not include: - Mandatory extra cleaning in case of animals (€ 50,00/week/animal), - Tourism tax (where applicable). Villa Rinaldi, just a few kilometres from the centre of Siena, is immersed in the green of the centuries-old trees of the Montagnola Senese Park, an authentic green lung considered a "Site of Community Importance" by virtue of the geological and botanical heritage that characterises it. The villa is located along a residential road in the small borgo of Santa Colomba, dominated by a 14th century castle-fortress and a small church, originally a watchtower, adorned with frescoes by Duccio da Buoninsegna. It occupies the ground floor of an elegant building, lovingly renovated by the current owners who live there (with discretion on the upper floor) only for short periods. Three large, elegant bedrooms with private bathroom and air conditioning, a cosy open-plan dining room and kitchen and an elegant sitting room that opens onto the fully-equipped garden, add value to the structure which is surrounded by a wonderful park immersed in the quiet of a wood of holm oaks, oaks and chestnut trees in the background. Walking in the undergrowth around the villa, you encounter an enchanted nature made up of strawberry trees, cyclamen and honeysuckle where you can stop and admire the landscape that stretches up to the towers of Siena. Villa Rinaldi is the deal place for those who want to spend a holiday dedicated to eco-sustainable tourism where nature is the protagonist. The Montagnola area, in fact, with its marked CAI (Club Alpino Italiano) trails and gentle hills is ideal for hikers, for those who love trekking or simply strolling around, enjoying the unspoiled nature and immersing themselves in the history, art and culture of the territory. It is also an incredible concentration of castles (Monteriggioni, Chiocciola, Celsa), churches and hermitages of rare beauty that can often be reached on foot (San Leonardo al Lago, Lecceto), testifying to the thousand routes that were part of the Via Francigena, still travelled today. Interior: Villa Rinaldi is on the ground floor of the building and the main entrance, located on the side of the building, goes into an elegant hallway which leads, on the right, into the large living room with study corner and direct exit out to the garden and, on the left, to the kitchen and dining room. The sleeping area consists of a double bedroom (with divisible beds) with ensuite bathroom with tub, and two twin bedrooms (with joinable beds), both with ensuite bathroom with shower. The apartment is completed by the laundry room. Air conditioning in the bedrooms. Park: Simply idyllic is the one-hectare park, completely fenced and accessible, which extends to the rear of the building, marked along the perimeter by centuries-old oak trees and refreshing woody vegetation. The arboreal heritage and the sparkling symphony of flowers planted in every corner of the welcoming garden are simply remarkable. Within the park, along a path immersed in silence, you will find an authentic garden of Eden devoted to lazing around and conviviality, with various spots equipped with chairs and tables and a convenient dining area at the living room exit. The undergrowth is rich in junipers, honeysuckles, strawberry trees, ferns, cyclamens, violets, hellebores, strawberries and wild blackberries that you come across just by walking around the house. The park is completed by a vegetable garden with seasonal vegetables and herbs available to guests. The parking area is located just past the entrance gate to the property.Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens’ grass could be different at the moment of your arrival at the villa. Swimming Pool: The swimming pool is located in the most discreet area of the property, on lower terracing about 20 m from the villa and reached down a few steps or down a path. Rectangular, with submerged steps for acess to the water, the pool measures 4 x 8 m with the depth varying from 1.50 to 1.70 m. Lined in PVC with a stone-paved border, it is equipped with internal spotlights, salt purification and a waterproof cover for the night. The surrounding sunbathing area is equipped with a large umbrella, small tables and sofas, sunbeds and a cold-water shower. The pool is open from the last Saturday in April until the first Saturday in October. Pets: Yes. € 50,00 per animal per week to be paid on site Extra On Request: - Extra cleaning (€ 22,00/hour per cleaner), - Extra linen (€ 15,00 per person), - Heating (on consumption up to date market prices) - Firewood (€ 20,00/100 Kg) Property Registration Number: 052016LTN0057

Cresta del Chianti

Castelnuovo Berardenga, IT
11 Bedrooms 18 Guests
Aug 29 - Sep 5
$1,668 night

Cresta del Chianti is a beautifully restored stone farmhouse in a peaceful hilltop location, surrounded by well-kept gardens with flowering plants, olive trees and vineyards. The large pool offers sweeping views across the iconic Chianti Classico landscape. With generous space both indoors and out, this holiday home is perfect for large families or groups looking to celebrate a special occasion or enjoy a relaxing stay in a beautiful setting. Located in the heart of the Chianti Classico, Cresta del Chianti is an ideal base for exploring the region. The Dievole Wine Resort, just three kilometres away, offers wine tastings and an excellent restaurant. The scenic Dievole Nature Path follows historic trails once used by sharecroppers and is ideal for walking, cycling or horseback riding. The small village of Vagliagli with its local restaurant is only two kilometres away. Castellina in Chianti can be reached in fifteen minutes by car and offers shops, restaurants and the popular Gelateria di Castellina. Art lovers will enjoy the nearby Chianti Sculpture Park. Siena is just thirty minutes away, and Florence, Arezzo and San Gimignano are also within easy reach for day trips. The house is spread across three floors. The ground floor offers spacious living and dining areas for everyone to gather. On the upper floors, smaller seating and living areas provide space for peace and privacy. The tasteful interior features traditional wooden beam ceilings, impressive fireplaces, light décor and carefully selected furnishings. A special highlight is the underground pool house with kitchen, lounge area, gym and table tennis. The large garden also includes a children’s play area and a volleyball court, offering extra fun for guests of all ages. Ground Floor Entrance Hall Kitchen Fully equipped, middle unit with three chairs, double gas oven and hob with six rings, 2 dishwashers. Dining Area Table and 6 chairs, kitchen cupboards, American style fridge/ freezer, French door to terrace, terrace with table and chairs. Lounge One corner sofa, two armchairs, two coffee tables, two chairs, two glass side tables, open fireplace, little bar with fridge and sink, three French doors to the terrace, glass enclosed terrace with table and 18 chairs, 4 air conditioning units. Bathroom Sink, WC. TV and Study Room TV with cabinet, two desks with chairs, one sofa, coffee table, two chairs, table with four chairs, glass side table, door to garden, air-conditioning. Bedroom 1 Double bed (cannot be converted into a twin beds), wardrobe, bedside tables, door to garden, chest of drawers, air-conditioning. Bedroom 2 Single bed, chest of drawers, air-conditioning. Bathroom Shower, sink, WC. First Floor Reception Room Round table with four chairs, glass side table, sofa. Bedroom 3 Twin beds (can’t be converted into a double bed), bedside table, air-conditioning. En-suite Bathroom Shower, sink, WC. Bedroom 4 Double bed (cannot be converted into a twin beds), bed side tables, wardrobe, armchair, table, air-conditioning. En-suite Bathroom Shower, sink, WC. Lounge Table and six chairs, French dresser, sofa, open fireplace, doors to garden. Bedroom 5 Twin beds (can’t be converted into a double bed), wardrobe, bed side table, air-conditioning. Bathroom Shower, sink, WC. Bedroom 6 Double bed (cannot be converted into a twin beds), bed side tables, wardrobe, chest of drawers, air-conditioning. Bedroom 7 Double bed (cannot be converted into a twin beds), bed side tables, wardrobe, air-conditioning. Bathroom Shower, sink, WC. Bedroom 8 Double bed (cannot be converted into a twin beds), bed side tables, open fireplace (decoration only), wardrobe, chest of drawers, air-conditioning. En-suite Bathroom Shower, sink, WC. Suite Lounge Table and six chairs, sofa, side table, 2 chairs. Bedroom 9 Double bed (cannot be converted into a twin beds), bed side tables, wardrobe, air-conditioning. En-suite Bathroom Shower, sink, WC. Second Floor Lounge Table and 6 chairs, sofa, glass side table. Bedroom 10 Single bed, bed side table, wardrobe, doors to a small terrace, air-conditioning. Bathroom Shower, sink, WC. Bedroom 11 Double bed (cannot be converted into a twin beds), bed side tables, wardrobe, air-conditioning. En-suite Bathroom Bath, sink, WC, handheld shower. Basement ( access externally) Washing machine, dryer and ironing facilities Underground Pool-House Kitchen, sofa, TV, snooker table, air conditioning, gymnasium, table tennis, foosball. Wine cellar (entry available on request) Private Pool: Length: 17 m Width: 8 m Depth: 1.3 - 3 m Entrance: Roman steps & ladder Opening times: April to September Fenced: No Furnished: 12 Sunlounges, gazebo, 2 chairs Cleansed: Chlorine Distance from villa: 50m Baby pool is 3x3 m and 1.10 m deep. 6 cars not sheltered Local charges Tourist tax: 4.00 € per person, per night for the first 7 nights, some exemptions apply. Arrival guide Approach road: Paved Parking: Private, onsite parking

San Marcellino

Gaiole in Chianti, IT
5 Bedrooms 10 Guests
Aug 29 - Sep 4
$2,180 night

San Marcellino is a beautiful holiday home located on the Rocca di Montegrossi wine estate in the heart of Chianti Classico. Surrounded by vineyards and rolling hills, it offers stunning panoramic views, expansive gardens, and a large pool - the perfect setting for a relaxing holiday with family or friends. The location combines peace with excellent access. The village of Monti, with a good restaurant, is a 20-minute walk away. Gaiole in Chianti, with more restaurants, shops, and a small supermarket, is just 14 kilometers away. Siena can be reached in about 30 minutes by car, and San Gimignano, Florence, and Arezzo are all ideal for day trips. San Marcellino lies in a tranquil, rural setting, nestled in the unspoiled Tuscan landscape. Built from traditional stone, the property blends harmoniously into the Mediterranean gardens, with wide green spaces that invite you to linger. The generous pool area offers ample space for relaxing, sunbathing, and enjoying the beauty and peace of the surroundings. The accommodation consists of a two-storey main house, a separate cottage, and a small annex – ideal for two guests each, combining privacy with shared time. Each unit includes its own kitchenette and a covered terrace. Inside, white-painted wooden beam ceilings and cream-colored walls create a light and airy atmosphere. Carefully selected furnishings complete the elegant and welcoming interior. The price includes a daily morning cleaning service of four hours. Upon request, a breakfast basket with fresh bread, croissants, and focaccia can be delivered. A staff member is also available to set the breakfast table, serve drinks, and clean the kitchen afterward. First Floor Lounge Sofas, chairs, coffee table, fireplace, side table, wooden trunk, door to balcony, balcony with table and chairs, air-conditioning. Dining Room Table, chairs, display cabinet, side table, air-conditioning. Kitchen Fully equipped kitchen, induction hob, fridge/freezer, table, and barstools, air-conditioning. Bedroom 1 Double bed (can be converted into twin beds), bedside tables, luggage stand, chest of drawers, chair, built-in wardrobe, air-conditioning. En-suite Bathroom Shower, double sink, bidet, WC, air-conditioning. Bedroom 2 Four poster double bed (cannot be converted into twin beds), bedside tables, bench, built-in wardrobe, air-conditioning. En-suite Bathroom Shower, double sink, bidet, WC, air-conditioning. Bedroom 3 Double bed (cannot be converted into twin beds), bedside tables, bench, wardrobe, luggage stand, chest of drawers, air-conditioning. En-suite Bathroom Bath with shower attachment, double sink, bidet, WC. Second Floor Snug Sofa, TV, side table, air-conditioning. Cottage Ground Floor Suite 1 (separate entrance) Bedroom 4 Double bed (cannot be converted into twin beds), bedside tables, bench, luggage stand, TV, side table, built-in wardrobe, doors to terrace, terrace with table and chairs, air-conditioning. En-suite Bathroom Shower, sink, bidet, WC, air-conditioning. Kitchenette Fully equipped kitchen, electric hob, fridge, doors to terrace, terrace with table and chairs, air-conditioning. Annex Ground floor Suite 2 (separate entrance) Bedroom 5 Double bed (can be converted into twin beds), bench, bedside tables, chest of drawers, built-in wardrobe, doors to terrace, terrace with table and chairs, air-conditioning. En-suite Bathroom Shower, double sink, bidet, WC, air-conditioning. Kitchenette Fully equipped kitchen, electric hob, fridge, air-conditioning. Private Pool: Length: 12 metres Width: 4 metres Depth: 1.5 metres Entrance: Roman steps Opening times: May to mid October Fenced: No Furnished: Sunloungers, gazebo and parasols Cleansed: Salt Distance from villa: 10m 3 cars sheltered Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Charged based on usage: EV Charge Point Arrival guide Approach road: Unpaved, even Parking: Private, onsite parking

The Ultimate Villa with Stunning Views, Tuscany Villa 1134

Tuscany, IT
8 Bedrooms 16 Guests
Aug 29 - Sep 2
$1,486 night

5 Star Villa Holidays is proud to present Tuscany Villa 1134. 8-room house 314 m2 on 2 levels. Comfortable and cosy furnishings: open living room with open-hearth fireplace and satellite TV. 2 double bedrooms. Living room with open-hearth fireplace and satellite TV. 1 double bedroom. 1 small room with 1 bed. Open gallery with sloping ceilings with 1 bed. Living room with satellite TV. 2 double bedrooms. Open kitchen (4 hot plates, oven, dishwasher, freezer). 4 showersbidetWC. Upper floor: open living room with open-hearth fireplace and satellite TV. 2 double bedrooms. Open kitchen (4 hot plates, oven, dishwasher, freezer). 2 showersbidetWC. Gas heating (extra). Heating available only from 01.11. to 15.04. Terrace furniture, barbecue. Very beautiful view of the countryside. Facilities: washing machine, children’s high chair, baby cot. Internet (WiFi, free). 1 pet dog allowed.Tuscany Villa 1134, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhouse which is divided into three apartments (for 14 people) communicating with each other from the outside and the annex (for 02 people) country house ’Tuscany Villa 1134’, 400 m a.s.l.. 2 houses in the residence. 5.8 km from the centre of Castellina in Chianti, 26 km from the centre of Siena, 42 km from the centre of Firenze, in a secluded, quiet, sunny position on top of a hill, in the countryside. Private: garden 1 ha (fenced), swimming pool fenced (12 x 6 m, depth 120 - 240 cm, 01.04.-31.10.). Outdoor shower, table tennis, pergola, garden furniture, barbecue. Heating to be paid on the spot (01.11.-15.04.), heating available only from 01.11. to 15.04.. Motor access to the house (1.5 km via unmade road). Roofed, parking on the premises. Grocery 5.8 km, supermarket 5.8 km, restaurant 5.8 km, thermal baths ’Rapolano Terme’ 50 km. Nearby attractions: San Donato in Poggio 16 km, Radda in Chianti 16 km, Monteriggioni 18 km, Gaiole in Chianti 19 km, Greve in Chianti 25 km, San Gimignano 47 km.

Campanella Estate – Luxury Tuscan villa with private pool

Monteroni d'Arbia, Toscana, IT
31 Bedrooms 59 Guests
Oct 31 - Nov 3
$3,878 night

CAMPANELLA ESTATE - SIENA AREA The Campanella Estate (1050 hectares) is a medieval country estate located in the heart of the Crete Senesi area, 25 km south of Siena. Suitable for groups of 59 people, the estate features two swimming pools, a tennis court, boccia ground, bikes, children’s playground, laundry room and restaurant. In the nearby towns of Monteroni d’Arbia and Asciano you will find shops, restaurants. The well-known wine centres of Montalcino and Montepulciano and, beautiful towns like Pienza, Arezzo and San Gimignano, are all within easy reach by car. The Campanella Estate consists of a private villa (600 sqm) and eleven apartments (1088 sqm). The villa has its own private garden and swimming pool and the apartments share a pool in the grounds of the estate. The villa and each apartment has its own private outside dining area. Please note that on the estate there is a restaurant which can be accessed by outside people. Villa (Sleeps 11) On the ground floor, you will find a large living room (with sofas and a fireplace), a dining room (with table seating sixteen), a well-equipped kitchen with all the modern conveniences. On this level, you will also find a TV room (with sofa), a bathroom (with toilet), a storage room, a laundry room, and a cellar. One the first floor, you will find a billiard room (with billiard table), two twin bedrooms (with two single beds) with ensuite bathrooms (with shower), three double bedrooms (with double beds) with ensuite bathrooms (with shower), and one single room (with single bed) with ensuite bathroom (with shower). Outside, the villa faces a private 17th century chapel (still used for mass on Sundays) and is surrounded by a well-maintained garden with a private swimming pool (6 m x 12 m; depth 1.1 m – 2.4 m; open 16 April – 22 October). Around the pool, you will find a sun terrace (with sun loungers and umbrellas) and next to the villa, there is a shaded terrace (with table seating sixteen) for outdoor dining. Facilities: Air conditioning (bedrooms only), Internet Wi-Fi, Satellite TV, Kitchen, Microwave, Fridge freezer, Oven, Microwave, Gas Hob, Coffee machine, Kettle, Iron/ironing board, Dishwasher, Washing machine, Bed linen (changed weekly), Towels (changed weekly), Pool towels (pay a refundable deposit), Garden, Terrace, Swimming pool, Sun loungers, Umbrellas, Outdoor dining, Tennis court, Bowls, Playground, Bikes, Billiards, Barbecue, Parking. Apartments (Sleep 48) Apartment one (Sleeps 6) In this 117 square metre, first floor apartment, you will find a living room (with sofas and a fireplace) and a well-equipped kitchen (with a table seating two). In the sleeping area, there are two double bedrooms (with double beds), one twin bedroom (with two single beds) and two bathrooms (with bath). Apartment two (Sleeps 5) In this 91 square metre, ground floor apartment, you will find a living room (with sofa and armchairs) and a well-equipped kitchen (with table seating four). In the sleeping area, you will find one double bedroom (with double bed), one twin bedroom (with two single beds), one single bedroom (with single beds), one bathroom (with shower) and one bathroom (with bath). Apartment three (Sleeps 4) In this 84-square metre, first floor apartment, you will find a living room (with a fireplace) and a well-equipped kitchen (with a table). In the sleeping area, you will find one double bedroom (with double bed) with ensuite bathroom (with shower), one twin bedroom (with two single beds) and one bathroom (with bath). Air conditioning is available. Apartment four (Sleeps 4) On the ground floor of this two-floor, 114-square metre apartment, you will find a living room (with a fireplace) with a sitting area (with sofas) and a dining area (with table seating four). On this level, you will also find a well-equipped kitchen (with table seating four). On the first floor, you will find one double bedroom (with double bed) with ensuite bathroom (with shower), one twin bedroom (with two single beds) and one bathroom (with bath). Apartment five (Sleeps 6) In this 121-square metre apartment, you will find three floors with the main entrance on the middle floor. Here, you will find a well-equipped kitchen (with a table), a twin bedroom (with two single beds) and one bathroom (with shower). A staircase leads you down to the ground floor where you will find a large living room (with sofas, a fireplace, and a table seating six). On the third floor, you will find a double bedroom (with double bed), a twin bedroom (with two single beds) and one bathroom (with bath). Air conditioning is available. Apartment six (Sleeps 4) On the ground floor of this two-floor, 124-square metre apartment, you will find a large living room with a sitting area (with sofas) and a dining area (with table seating four) and a separate, well-equipped kitchen (with a table seating four). On the first floor, you will find one double bedroom (with double bed), one twin bedroom (with two single beds), one bathroom (with bath) and one bathroom (with shower). Apartment seven (Sleeps 4) In this 80 square metre, ground floor apartment, you will find a living room with a sitting area (with sofas), a dining area (with table seating four) and a well-equipped kitchen. In the sleeping area, you will find one double bedroom (with double bed) with ensuite bathroom (with shower), one twin bedroom (with two single beds) with ensuite bathroom (with bath). The apartment has a private terrace (with table and chairs) for outside dining. It is also suitable for the disabled. Apartment eight (Sleeps 3) In this 83-square metre, first floor apartment, you will find a large living room with a sitting area (with sofas and a fireplace) and dining area (with table seating four). There is a separate well-equipped kitchen, and in the sleeping area you will find one double bedroom (with double bed), one single bedroom (with single bed) and two bathrooms (with shower). Apartment nine (Sleeps 6) On the ground floor of this two-floor, 124-square metre apartment, you will find a large living room with a sitting area (with sofa), dining area (with table seating eight) and a well-equipped kitchen area. On this level you will also find a bathroom (with toilet). On the first floor, you will find one double bedroom (with double bed), two twin bedrooms, one bathroom (with bath) and one bathroom (with shower). Apartment ten (Sleeps 4) On the ground floor of this two-floor, 90-square metre apartment, you will find a living room with a sitting area (with sofas), a dining area (with table seating four) and a well-equipped kitchen area. In the sleeping area, you will find one double bedroom (with double bed), one twin bedroom (with two singles beds) and two bathrooms (with shower). A spiral staircase from the living room leads to a mezzanine floor (with sofa and TV). The apartment has a private terrace (with tables and chairs) for outside dining and air-conditioning. Apartment eleven (Sleeps 2) In this 60-square metre, first floor apartment, you will find a living room (with double sofa bed) and a kitchen/diner (with table seating four). In the sleeping area, you will find one double bedroom with ensuite bathroom (with shower) and one bathroom/utility room (with toilet and washing machine). The apartment has a private outdoor terrace (with table seating four and an umbrella) and air conditioning. Facilities: Air conditioning (apartments 3, 5, 10 & 11 included in price), Internet Wi-Fi, Satellite TV, Kitchen, Oven, Hob, Fridge freezer, Dishwasher, Coffee machine, Toaster, Washing machine (2), Dryer, Bed linen (changed weekly), Towels (changed weekly), Pool towels (refundable deposit), Garden, Swimming pool, Terrace, Sun loungers, Outdoor dining, Barbecue, Tennis Court, Bikes, Parking. Outside, the Campanella Estate is set in 1050 hectares of grounds surrounded by tall trees and flowering hedges with a large well-maintained garden and a swimming pool (16 m x 8 m; depth 0.95 m – 1.5 m; open 14 April – 22 October). In the outside living space, you will find a sun terrace (with sun loungers and chairs) and each apartment has its own private outside dining area (with tables and chairs). The estate also features a barbecue area, tennis court, bowls ground, bikes and children’s playground, which guests can use free of charge. Sleeps: 59 Code: TU963

Villa Vinsantaia

Gaiole in Chianti, IT
2 Bedrooms 2 Guests
Sep 26 - Oct 1
$512 night

Villa Vinsantaia, located on the edge of the charming village of San Sano, offers an authentic and tranquil escape in the heart of Tuscany’s renowned Chianti Classico wine region. Once a historic site for drying grapes for Vin Santo wine, this villa provides panoramic views of some of the world’s most famous vineyards, making it a perfect retreat for a couple or small family. Just a short walk to the village centre, guests can enjoy the delightful La Grotta della Rana restaurant and a small grocery shop. Thanks to its central location, the villa is perfectly positioned for exploring the best of the region. Scenic drives through the Chianti countryside lead to nearby towns, renowned wineries, and charming villages. Siena, San Gimignano, Florence, and Arezzo are all within easy reach and make for unforgettable day trips. Gaiole in Chianti is just a ten-minute drive away and offers additional restaurants, shops, a COOP supermarket, and bike rentals. The villa is surrounded by a spacious garden, complete with a shaded terrace for outdoor dining and an inviting infinity pool just steps from the villa. Inside, traditional wooden beams combine with modern comforts, including cool travertine floors and stylish furnishings. Owned by a local winery, Villa Vinsantaia offers a unique connection to the region’s wine heritage, with wine tastings just a leisurely stroll away. Immerse yourself in Tuscany’s beauty, culture, and tradition, while savouring the finest wines and enjoying a peaceful, unforgettable getaway. Ground Floor Kitchen/ Diner/ Lounge Fully equipped kitchen, induction hob, fridge/freezer, table, chairs, sofa, TV, fireplace (decoration only) washing machine, metal staircase to mezzanine floor, French door to terrace, terrace with table and chairs. Bedroom 1 Double bed (can be converted into twin beds), bedside tables, chairs, mosquito screen, air-conditioning. En-suite Bathroom Shower, sink, bidet, WC, wardrobe. Bathroom Shower, sink, bidet, WC Mezzanine Floor Bedroom 2 (low ceiling height 1,50m) Twin beds (can be converted into double bed), bedside tables, chair, wardrobe, mosquito screen. Private Pool Length: 9 meters Width: 4 meters Depth: 1.4 meters Entrance: Roman steps Opening times: April to October Fenced: No Furnished: Sunloungers and parasols Cleansed: Salt Distance from villa: 4 meters 3 uncovered spaces Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Dog up to 30kg: 10.00 € daily charge Charged based on usage: Heating Villa, Air Conditioning Arrival guide Approach road: Paved Parking: Private, onsite parking

Valliole

Gaiole in Chianti, IT
4 Bedrooms 8 Guests
Sep 26 - Oct 1
$665 night

Valliole is a 17th-century villa in the Chianti region with breathtaking postcard-perfect views across the vineyards of Chianti Classico. Set on a hill in peaceful countryside, this spacious and beautifully maintained property comfortably accommodates up to eight guests and is ideal for a relaxing holiday with family or friends. The large infinity pool with panoramic views is one of many highlights. A covered terrace and several outdoor seating areas provide plenty of space to come together or retreat for quiet moments. The location is perfect for exploring the region’s renowned wineries and castles. The prestigious Castello di Ama is just over a kilometre away and also features an impressive collection of contemporary art. The Chianti towns and villages are within easy reach, and cities such as Siena, San Gimignano, Florence and Arezzo are perfect for day trips. Radda, with its restaurants, shops and supermarket, is 15 minutes away by car. The charming villages of Lecchi and San Sano can also be reached on foot in under 30 minutes. Each has a restaurant and a small grocery store. The property comprises a two-storey main house and a separate guesthouse for two guests, ideal for those seeking extra privacy. Inside, original terracotta floors and wooden beam ceilings are combined with elegant furnishings and contemporary art. Valliole is a timeless Tuscan retreat that combines history, beauty and comfort in one unforgettable setting. Ground Floor Hall Cupboard, console table, chair, fireplace, stairs to first floor, entrance. Lounge-Diner Two sofas, two chairs, woodburning stove, table and chairs, cupboard, two sets of doors to terrace. Kitchen Fully equipped. First Floor Library Table, two chairs, wood burning stove. Bedroom 1 Twin beds (can be converted into a double bed), two wardrobes, table. En-suite Bathroom Shower, sink, WC. Bedroom 2 Double bed (cannot be converted into twin beds). En-suite Bathroom Bath, shower, WC, Sink Bedroom 3 Double bed (cannot be converted into twin beds) Bathroom Bath, shower, twin sinks, WC. Separate Annexe Kitchen-Diner Well-equipped kitchenette, table and chairs, door to terrace. Master Bedroom Double bed (cannot be converted into twin beds), wardrobe, two chairs. Bathroom Jacuzzi bath, shower, sink, WC. Private Pool Length: 12 meters Width: 6 meters Depth: 1.4 metres Entrance: Roman steps Opening times: Easter to October Fenced: No Furnished: Sunloungers, parasols, pergola, benches and outside shower, WC Cleansed: Chlorine Distance from villas: 3 meters 5 covered spaces Local charges Charged based on usage: Heating Villa Arrival guide Approach road: Unpaved, even Parking: Private, onsite parking

Villa Agresto

Gaiole in Chianti, IT
6 Bedrooms 12 Guests
Aug 30 - Sep 3
$1,582 night

Villa Agresto is an elegant stone villa set in a private position on a hilltop, surrounded by the vineyards of the renowned Ricasoli estate. Its peaceful countryside setting and large garden with mature trees offer guests plenty of privacy and welcome shade on warm summer days. From this elevated location, guests enjoy uninterrupted 360-degree views over the picture-perfect landscape of the Chianti Classico. With spacious interiors, extensive grounds, and a generous pool, the villa is ideal for a holiday with a large family or a group of friends. Thanks to its excellent location in the heart of Chianti, the region’s most famous towns, villages, wineries and castles are all within easy reach. The popular town of Gaiole in Chianti, with restaurants, shops and a supermarket, is only a 20-minute drive away. For fine dining, head to the tiny village of Villa a Sesta, home to two Michelin-starred restaurants. Just 2.5 km from the villa, guests can visit the historic Castello di Brolio, the ancestral home of the Ricasoli family, to tour the castle and taste their celebrated wines. Siena, Florence, Arezzo and San Gimignano are all perfect for day trips. This two-storey villa, built from traditional stone, features several covered loggias furnished with dining tables and seating areas – ideal for relaxed evenings and time spent together. Inside, the décor is tastefully composed, with original beamed ceilings, terracotta floors, wooden accents and soft, harmonious colours. Stylish yet comfortable furnishings create an atmosphere where guests immediately feel at home. Villa Agresto is the perfect choice for those seeking peace, comfort and the essence of Tuscan living in a truly special setting. Ground Floor Dining Room Dining table with 12 chairs. Kitchen Fully equipped kitchen, gas hob with 4 rings, island, 2 stools. Bedroom 1 Double bed (can be converted into twin beds if requested when booking), wardrobe, chest of drawers, chair. En-suite Bathroom Shower, bidet, sink, WC. Bedroom 2 Double bed (cannot be converted into twin beds), chest of drawers, 2 chairs. En-suite Bathroom Shower, bidet, sink, WC. First Floor Atrium Sofa Lounge 2 sofas, 2 armchairs, TV, open fireplace, desk and chair. Bedroom 3 Pair of twin beds (cannot be converted into a double bed), wardrobe, chest of drawers, desk and chair, chair. Bedroom 4 Double bed (can be converted into twin beds if requested when booking), wardrobe, chest of drawers. Bedroom 5 Pair of twin beds (cannot be converted into a double bed), wardrobe, chest of drawers. En-suite Bathroom Shower, bidet, sink, WC. Bedroom 6 Double bed (cannot be converted into twin beds), chest of drawers, chair. En-suite Bathroom Shower, bidet, sink, WC. Bathroom Bathtub with shower attachment, bidet, sink, WC. Private Pool: Length: 12 metres Width: 6 metres Depth: 1.2 to 2.0 metres Entrance: Metal ladder Opening times: May to September Fenced: Yes Furnished: Sunloungers and parasols Cleansed: Chlorine Distance from villa: 20 metres Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Dog up to 30kg: 10.00 € daily charge Charged based on usage: Heating Villa, Air Conditioning Arrival guide Approach road: Unpaved, uneven, high clearance vehicle recommended Parking: Private, onsite parking

Poggio Tondo

Castellina in Chianti, IT
3 Bedrooms 6 Guests
Sep 26 - Oct 3
$520 night

Poggio Tondo is a spacious country house in complete seclusion, set on a hill in the heart of the Chianti Classico. Surrounded by cypress trees and forest, it offers sweeping panoramic views of olive groves, vineyards, the rolling hills of Chianti and, in the distance, the skyline of Siena. With a well-kept garden, large terrace, and a beautiful pool, it is the perfect setting for a relaxing holiday with family or friends. The location is peaceful and rural, yet very well connected. The wineries Castello di Fonterutoli and Tregole can both be reached on foot. Castellina in Chianti is only four kilometres away and offers restaurants, cafés, a supermarket, and the popular Gelateria di Castellina, known for its delicious ice cream. Siena is less than half an hour away by car. San Gimignano, Florence, and Arezzo also make great destinations for day trips. The two-storey stone house with brown wooden shutters and a full-length balcony on the upper floor has the character of an alpine retreat but fits naturally into the Tuscan setting. The large terrace at the front opens out onto the garden and pool area, perfect for enjoying the outdoors. Inside, Poggio Tondo features a bright, welcoming atmosphere with tiled floors and comfortable, spacious interiors. Both floors include living and dining areas as well as kitchens. The upstairs living room opens onto the balcony, an ideal spot for morning coffee or a quiet evening with a view. Poggio Tondo offers space, privacy, and nature in perfect harmony. Ground Floor Lounge/ Diner Sofas, coffee table, TV, fireplace, side tables, long dining table, chairs, chest of drawers, mosquito screen. Kitchen Fully equipped, gas hob with 5 rings, diswasher, fridge/ freezer, chairs, mosquito screen. Bathroom Shower, sink, bidet, WC, mosquito screen. First Floor Lounge/ Diner Sofas, coffee tables, TV, table chairs, Welsh dresser, French doors to a large balcony, balcony with table and chairs, mosquito screen. Kitchen Fully equipped, gas hob with 5 rings, diswasher, fridge/ freezer, chairs, washing machine, mosquito screen. Bedroom 1 Double bed (cannot be converted into twin beds), wardrobe, chair, baby cot, ceiling fan, mosquito screen. Bathroom Shower, sink, bidet, WC, mosquito screen. Bedroom 2 Double bed (cannot be converted into twin beds), bedside tables, wardrobe, chest of drawers, ceiling fan, mosquito screen, French door to balcony. Bedroom 3 One single and one French-size bed (can’t be converted into a double), bedside table, wardrobe, ceiling fan, mosquito screen. Bathroom Shower, sink, bidet, WC, mosquito screen. Private Pool Length: 12 m Width: 4 m Depth: from 1,20 m to 1,60 m Entrance: Roman steps Opening times: always open Fenced: no Furnished: parasol, deckchairs, sundoungers Cleansed: chlorine Distance from the villa: 26 m 2 uncovered spaces Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Dog up to 30kg: 9.00 € daily charge per pet Charged based on usage: Heating Villa Arrival guide Approach road: Unpaved, even Parking: Private, onsite parking

Idyllic countryside villa with garden and pool

Barberino Tavarnelle, IT
5 Bedrooms 10 Guests
Aug 29 - Sep 5
$2,087 night

Villa Tignano has been recently fully renovated, blending a warm and elegant atmosphere with original features such as terracotta floors and exposed-beam ceilings, combined with modern comforts and designer furnishings. The villa spans two levels plus the traditional “Piccionaia” and is surrounded by expansive green areas on all sides. Guests also enjoy exclusive use of a private swimming pool. On the ground floor, an elegant entrance hall opens to a living area centered around a large stone fireplace. This cozy, welcoming space includes a sitting area and a rustic yet contemporary dining room. Both the entrance hall and dining room connect to a fully equipped, professional-sized modern kitchen. At the back of the kitchen, a small breakfast nook opens onto the garden, ideal for light meals or morning coffee. From the main dining room, a few steps lead down to the grand living room, flooded with natural light through multiple large French doors opening to the garden. The room features a large fireplace, a huge sofa, and additional seating areas. This floor also includes a small fitness room, a full bathroom with shower, and an additional guest bathroom. The upper floor hosts the sleeping area with 5 double bedrooms, each uniquely furnished with original elements and individual character. Four bedrooms are along a charming corridor featuring modern decorative touches harmoniously paired with restored original doors. Three full bathrooms, some with both showers and bathtubs, serve the bedrooms. A cozy sitting area with ample storage provides access to the top level, the “Piccionaia,” which houses the fifth bedroom with en-suite bathroom. The large private pool is situated just below the villa, with a fenced access for safety. The pool deck is furnished with sun loungers, umbrella, and relaxation area. Open from April to the end of October, the pool is not heated. The villa is set within extensive green grounds, with multiple outdoor living areas offering breathtaking views of the surrounding villages. A romantic veranda provides the perfect spot for alfresco dining in summer. Private parking is available for guests. HOME TRUTHS - A car is required to reach the villa. - The property is not designed for parties or events; any such activity requires prior authorization. In any case, please turn off the music and keep noise to a minimum after midnight out of respect for the neighbors. - Air conditioning is available only in the bedrooms. - This is a NON-SMOKING property. - There are stairs inside the property (no elevator). - Access to the pool is via a small path. -Extra cleaning of 350 euro is included when booking online at the last step OTHER THINGS TO KNOW CIR 048054LTN0137 CIN IT048054C2POEU7A7T When you make a booking, you confirm the agreement to rent directly from the owner, who is an individual. Shortly after, you will receive the contract. Additionally, we will send you confirmation of the services our company will provide to make your stay as smooth as possible. We will be on hand to offer you the support needed to access and enjoy the rented property License number: IT048054C2POEU7A7T

Casa dei Mandorli

Gaiole in Chianti, IT
1 Bedrooms 2 Guests
Sep 29 - Oct 4
$408 night

Perched high in the scenic Ama hills, Casa dei Mandorli offers a peaceful retreat for a couple, with sweeping views over a patchwork valley of olive groves and vineyards stretching to the horizon. The nearby hamlets of Ama and Casanova di Ama add charm to the landscape, while the large infinity pool provides a striking focal point for outdoor living. The villa is perfectly situated between the hilltop town of Radda in Chianti and the idyllic village of Lecchi in Chianti, offering a balance of tranquillity and convenience. Lecchi is home to the excellent Ristorante Malborghetto and a well-stocked grocery shop, while Radda offers a wider range of shops, restaurants, and a small supermarket. Historic landmarks such as Castello di Brolio and several renowned Chianti Classico wineries are within easy reach. Siena, Florence, Arezzo, and San Gimignano are also ideal destinations for memorable day trips. Built from traditional stone, Casa dei Mandorli blends rustic character with modern elegance. The beautifully maintained garden includes lawns and a large terrace set just above the private pool - an ideal spot for al fresco dining or simply enjoying the views. Inside, the villa is bright and welcoming, with contemporary country-style furnishings. The open-plan kitchen, dining and living area features large arched windows and doors that frame the surrounding garden and bring the outdoors in. The discreet owners live in a separate villa above, with two friendly dogs kept within a fenced area. They are available if needed and offer helpful local recommendations, contributing to a relaxed and memorable stay at Casa dei Mandorli. Ground Floor Lounge/ Diner Sofa, side tables, dining table, glass cabinet, chairs, fireplace (decoration only), TV, chest of drawers, air-conditioning, French door to terrace. Kitchen Fully equipped, induction hob, fridge/freezer. Bedroom Double bed (can’t be converted into twin beds), bedside tables, wardrobe, desk, chair, air-conditioning. En-suite Bathroom Shower, sink, bidet, WC. Private Pool (infinity) Length: 11 metres Width: 5 metres Depth: 1.5 metres Entrance: Roman steps Opening times: May to October Fenced: No Furnished: Pergola, table, chairs, sunloungers and parasols Cleansed: Chlorine Distance from villas: 5 metres 1 unsheltered space Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Charged based on usage: Heating Villa, Air Conditioning Arrival guide Approach road: Unpaved, even Parking: Private, onsite parking

Villa Solatio

Gaiole in Chianti, IT
4 Bedrooms 8 Guests
Aug 27 - Sep 1
$706 night

Villa Solatio is a former farmhouse that has been restored with great care and respect for its history. Today, this charming holiday home combines authentic Tuscan character with a high level of comfort. Set on a fourteen-hectare estate in the Chianti Classico, surrounded by olive groves, vineyards and oak forests, it offers an ideal setting for a relaxing and genuine Tuscan stay. The location in the heart of Chianti provides easy access to the region’s renowned wineries, castles and picturesque towns. Siena, San Gimignano, Florence and Arezzo are all within convenient reach for day trips. Lecchi, four kilometres away, offers the well-known Ristorante Malborghetto and a small, well-stocked grocery shop. Additional shops and restaurants can be found in Radda, six kilometres away. The outdoor areas highlight the beauty of the property. A courtyard beneath a pergola covered with old vines sits just outside the kitchen, creating a delightful space for outdoor meals. Nearby are an outdoor kitchen with a grill and a former bread oven now used for pizza, as well as a sheltered dining area with a large table. A terrace runs along the side of the house, opening up views of the surrounding countryside. Terracotta planters filled with flowering plants and lemon trees add Mediterranean charm, while the generous pool lies just a few steps away. Inside, the rooms have been restored with sensitivity and attention to detail. Gently arched brick ceilings and rustic wooden beam ceilings lend a warm, traditional atmosphere. Terracotta floors and whitewashed walls provide a calm backdrop for artworks. A harmonious mix of rustic and contemporary furnishings, carefully selected textiles and decorative pieces creates a welcoming living environment. A retractable screen in the living room allows for enjoyable film evenings, complemented by a private billiard table. Ground Floor Kitchen Fully equipped, wood fire and gas fire oven, fridge/freezer, centred food preparation table, French doors to garden, terrace with two tables and chairs. Dining Room Table and chairs, piano, chests of drawers, French door to garden. Living Room 1 Billiard table, scoreboard, sofa, armchairs, chair, coffee table, bookshelves, side table, French doors to garden and one door to the pool area. Bathroom Sink, bidet, WC. Bedroom 1 Double bed (cannot be converted to twin beds), TV, bedside tables, chair, wardrobe, mosquito screens. En-suite Bathroom Shower, sink. First Floor Living Room 2 Sofas, coffee table, round table for playing cards with chairs, large working fireplace, side table, air-conditioning. Bedroom 2 Twin beds (can be converted into a double bed) one bedside table, table, chair, mosquito screens, air-conditioning. En-suite Bathroom Shower, sink, WC, shelf, air-conditioning. Bedroom 3 Double bed (cannot be converted to twins), two bedside tables, chair, wardrobe, mosquito screens, air-conditioning. En-suite Bathroom Shower, sink, WC, shelf, air-conditioning. Suite Lounge Two sofas, air-conditioning. Bedroom 4 Double bed (cannot be converted to twins), bedside tables, chest of drawers, desk and chair, wardrobe, mosquito screens, air-conditioning. En-suite Bathroom Bath, Shower, sink, WC, shelf, air-conditioning. Private Pool Length: 12 meters Width: 6 meters Entrance: Metal ladder Open: May to Sep Fenced: no Cleansed: Chlorine Furnished: Sunloungers, parasol, gazebo Distance from the villa: 10m 2 uncovered spaces Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Dog up to 30kg: 7.00 € daily charge per pet Charged based on usage: Heating Villa, Air Conditioning Arrival guide Approach road: Unpaved, uneven, high clearance vehicle recommended, uphill segments, experienced drivers recommended Parking: Private, onsite parking

Bellosguardo

Castellina in Chianti, IT
3 Bedrooms 6 Guests
Oct 3 - 10
$382 night

Bellosguardo is a charming Chianti holiday home set on a hill, offering stunning panoramic views over vineyards and the gentle, green hills of Chianti. This country house is the perfect choice for a holiday with family or friends. The beautifully maintained garden invites guests to relax, and the large pool provides the ideal spot for unwinding. Guests enjoy a peaceful location just a short drive from Castellina in Chianti . The villa is located in the heart of the Chianti Classico, with easy access to the region’s famous wineries, castles and picturesque villages. Siena is just a 30-minute drive away, and San Gimignano, Florence and Arezzo are all excellent options for day trips. The village of Quercegrossa is only 4 km away and offers a few restaurants and a small grocery store. Castellina in Chianti, about 15 minutes by car, has good restaurants, shops and a COOP supermarket. We especially recommend the delicious ice cream from the Gelateria di Castellina. The two-storey stone house features a covered terrace, perfect for shared meals and spending time together, as well as a balcony. Inside, the decor is cosy and comfortable, full of thoughtful details. Tuscan touches like vaulted brick ceilings combine with colourfully painted walls and artistic murals to create a warm and homely atmosphere. The owner lives next door, and there is an additional guest apartment with a separate entrance, occasionally used by the owner’s family and their guests. The pool is for the exclusive use of the holiday guests. Please note that pets are not allowed on the upper floor. Ground Floor Lounge Sofa, two armchairs, couch, writing bureau, chair, piano, fireplace, door to garden. Dining Room Table and chairs, couch, double doors to furnished terrace. Kitchen Main entrance, fully equipped, plus table and chairs. Laundry Room Fully equipped. First Floor Study Two armchairs, desk, bookcase, double doors to balcony. Bedroom 1 Twin beds (can be converted into a double), wardrobe, armchair, two chairs, mosquito screens. Bedroom 2 Double bed (cannot be converted into twins), wardrobe, chest of drawers, desk, chair, mosquito screens, double doors to balcony. Bedroom 3 Double bed (cannot be converted into twins), wardrobe, chest of drawers, mosquito screens. Bathroom 1 Shower, sink, WC. Bathroom 2 Bath, sink, WC Private Pool: Length: 13 metres Width: 6.5 metres Depth: 0.90 – 2.20 metres Entrance: Roman steps Opening times: May to September, weather permitting Fenced: No Furnished: Sunloungers Cleansed: Chlorine Distance from villa: 7 metres 2 uncovered spaces Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Charged based on usage: Heating Villa Arrival guide Approach road: Unpaved, even Parking: Private, onsite parking

Amazing Country Farmhouse with Lovely Wooden Beams

San Gusmé, IT
7 Bedrooms 14 Guests
Aug 23 - 28
$2,280 night

The price includes: - Utilities (water - gas for kitchen use - electricity) - pool and park maintenance - wireless internet connection - weekly linen, initial and final cleaning - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage to the property during your stay (up to the maximum of € 1,500.00 and with the limitations provided). The Price does not Include: - Mandatory extra cleaning in case of animals (€ 50,00/week/animal) - Tourist Tax(where applicable) RECEPTIVE STRUCTURE. Villa Santa Maria is a typical late-19th-century country farmhouse, fully restored and set within a wine estate in the heart of the Chianti Classico region. The stone-built house, respecting its original design, preserves wooden beams and terracotta tiles on the ceilings, terracotta floors, and a charming travertine staircase. From the windows, guests can enjoy stunning views over the surrounding countryside and hills, renowned worldwide. Staying at Villa Santa Maria means immersing yourself in the living reality of the farm: guests can book a private, tailor-made tasting experience of Chianti Classico, Riserva, and extra virgin olive oil, held directly on-site. The experience takes you through the Chianti Classico territory, the Berardenga area, and the history of Santa Maria, with the possibility of pairing the tastings with carefully selected local products. The hillside location ensures ideal temperatures for a pleasant stay, while the Villa’s position makes it a perfect starting point for excursions to charming Chianti Classico towns such as Castellina, Radda, and Greve, or to art cities like Florence and Siena. Interior: MAIN HOUSE. The main building is built on two levels. The ground floor, features a large living area with fireplace and TV which is connected to dining area and to the fully equipped kitchen. Also on this floor there is a double bedroom, a twin bedroom (with divisible bed) and two bathrooms, one with bath tub and one with shower and a storeroom. The entire ground floor is well connected to the outdoors by traditional French doors. From the ground floor an internal staircase leads to the upstairs which consists of a large living area with sofas and fireplace, Three double bedrooms (1 with divisible bed) with en-suite bathrooms (one with a bath tub and two with shower). DEPENDANCE. A few metres from the main house there is a dependance composed by a living room, a kitchenette, two double bedrooms, a bathroom with shower, an en-suite service bathroom. Park: The park cover an area of about 4 acres of lush olive groves and vineyards. Near the park, there is a rich forest that allows gusts to go for walks in the shade. At the back of the house, in a large brick paved room, equipped with two large sun umbrellas give shade to a table and chairs perfect for lunches and dinners whilst admiring the unique views over the Tuscan hills, beside is located the area with table tennis.Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens’ grass could be different at the moment of your arrival at the villa. Swimming Pool: The infinity pool, is about 30 meters from the house and is accessed via a staircase. The rectangular shaped pool measures 5 x 15m with a depth varying from 0.90 but 1.40 m. The depuration of the water is by salt. The pool area is equipped with sun beds in order to make the most of the sunny days in complete relaxation. The swimming pool is open from the last Saturday of April till the first Saturday of October Pets: Yes. € 50,00 per animal per week to be paid on site Extra on Request: - Linen change (€ 15,00/person) - Extra cleaning (€ 22,00/hour/cleaner) - Heating (on consumption up to date market prices - Firewood (€ 20,00/100 Kg) Property Registration Number: 052006AAT0072

Prestigious Airy Villa Overlooking the Ombrone Valley

Vescovado, IT
7 Bedrooms 21 Guests
Sep 30 - Oct 5
$991 night

The rate includes: - Utilities: electricity - water - gas for kitchen use and hot water - weekly linen, initial and final cleaning - Zer0Dep Guarantee = You do not pay the security deposit on balance or on arrival and you have EuropAssistance coverage in case of accidental damage caused to the property during your stay (up to the maximum of 1,500.00€ and with the restrictions provided). The rate does not include: Mandatory extra cleaning in case of the presence of animals (€50.00 per pet per week or part of the week). The admission of animals to the facility must be authorized in advance by the owner after communicating the number of animals, size and breed. Tourist tax (not required) Villa Angelini is an ancient historic residence located in the medieval village of Vescovado di Murlo, conveniently located a few steps from the town’s shops and services. Located in a hilly position, the villa enjoys a panoramic view that extends between olive groves and fields to the Val d’Ombrone and Montalcino. Arranged on three levels, the villa has the typical elements of Tuscan architecture, such as vaulted brick ceilings, terracotta floors and a decor that mixes period wooden furniture with classic rustic elements. The spacious interiors include seven bedrooms (in the full version), numerous living areas, a games room, and a professional kitchen, making the property ideal for large groups of all ages. Outside, a large garden houses a beautiful porch with a dining table. The location is ideal for visiting Tuscany’s vineyards, thermal baths and historic cities, with Siena about a 30-minute drive away. THE PROPERTY HAS UNDERGONE A CHECK-UP CARRIED OUT BY ONE OF OUR TECHNICAL MANAGERS, TO GUARANTEE THE CORRESPONDENCE OF THE DESCRIPTION, THE ACCESSORIES LISTED ON THE SITE AND THEIR STATE OF OPERATION/MAINTENANCE Interiors: The villa is spread over three floors. GROUND FLOOR — Entrance with corridor; old bread oven transformed into a games room with ping-pong table; three service bathrooms and laundry; large professional kitchen; dining room with fireplace; living room with sofas and TV. Most of the rooms on this level have large windows with direct access to the garden. FIRST FLOOR — Accessible via internal staircase or from the original main entrance of the villa; two double bedrooms with joinable beds and en-suite bathroom with shower; a double bedroom with en-suite bathroom with bathtub; the ancient kitchen, preserved with the original Tuscan fireplace. SECOND FLOOR — Accessible through a travertine staircase; four double bedrooms with en-suite bathroom with bathtub. It is possible to add a single bed in each of the rooms. Air conditioning in the rooms. Park: The villa is surrounded by about 6,500 square meters of fenced garden, distributed on different levels. The area in front of the house is paved with stone and lawn, with a shaded dining area covered by a large porch, wooden tables, umbrellas, barbecue and vases with flowers. Steps lead to a lower level planted with olive trees, shrubs and lawn, connected by stone paths. This area offers additional space for outdoor relaxation surrounded by greenery. N.B.: Please note that the photo shoots are usually carried out in spring, so the colors and blooms of the gardens, lawns and parks may be different when you enter the villa. Pool: The pool is located about 70 m from the villa and is completely fenced. Rectangular in shape, it measures 12 x 6 m with a maximum depth of 2.50 m; access to the water is via steps. The surrounding solarium is paved with travertine and furnished with sun loungers, tables, umbrellas and an outdoor shower. The pool is open from the last Saturday in April to the first Saturday in October. Extra On Request: extra cleaning (€ 22,00/hour/cleaner) extra linen (€ 15,00/person) heating (on consumption up to date market prices) firewood (€ 20,00/100 kg) Property Registration Number: 052019LTI0001

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