Vacation rentals in Siena, Italy with free parking

Explore 156 vacation rentals, homes, and villas with free parking in Siena for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Homes with Pools and Pet-Friendly Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. 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 personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

156 Homes with Free Parking in Siena

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

Refined Villa on the Hills with Tuscan Style

Siena, IT
4 Bedrooms 8 Guests
Aug 27 - 30
$1,132 night

Our Villa can be found just a few kilometers from the charming city of Siena. The Villa offers a splendid garden and a shared pool with a sunbathing and solarium area with comfortable loungers, as well as a large and spacious external area perfect for Al Fresco dining, WiFi and air conditioning. Bedroom 1: • 2 Single Beds or 1 Double Bed with Fresh Sheets and Pillowcases • External Bathroom with Shower, Bathtub , Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 2: • King-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: • 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 4: • Double-size Bed with Fresh Sheets and Pillowcases • Air conditioning • Free 24h Wi-Fi access The villa’s interiors are very bright and large with authentic and modern Tuscan furnishings arranged across the ground and first floor. Living Room The living room is provided with sofas that can accommodate up to 8 guests. There are many windows that let in natural light and a Flat TV. After the stairs to the first floor there is another spacious room with a ping pong table Dining Room The dining room is provided with a table with chairs for eight for enjoying your meal in the warm of the Villa. Al fresco dining External to the property you will find a table for al fresco dining, a sofas and armchairs for complete your relax Kitchen The typical tuscan kitchen is fully equipped with everything you need to prepare an unforgettable Italian dinner, including an oven, fridge and freezer, coffee maker, tea kettle, dishwasher, washing machine and toaster. A dream villa for families and groups of friends seeking nature, tranquility and authenticity

Villa Charming on the Hills | Mixed of Authentic and Modern Tuscan Style

Siena, IT
5 Bedrooms 10 Guests
Aug 27 - 30
$1,144 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 authentic and modern Tuscan Villa is a magnificent property consisting of 5 rooms and 5 bathrooms, that can accommodate large groups of guests of up to 10 people. Our Villa can be found just a few kilometers from the charming city of Siena. The Villa offers a splendid garden and a shared pool with a sunbathing and solarium area with comfortable loungers, as well as a large and spacious external area perfect for Al Fresco dining, WiFi and air conditioning. Bedroom 1: • 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 2: • 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 3: • 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 4: • Single Bed with Fresh Sheets and Pillowcases • Single Sofabed 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 The villa’s interiors are very bright and large with authentic and modern Tuscan furnishings arranged across the ground and first floor. Living Room The living room is provided with sofas and armchairs. There are many windows that let in natural light, a Flat TV, a complete chessboard and a spacious desk with chair. Dining Room The dining room is provided with a table with chairs for ten for enjoying your meal in the warm of the Villa. Al fresco dining External to the property you will find a table for al fresco dining, a sofas and armchairs for complete your relax Kitchen The modern 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 are also a breakfast bar with stools for 4 people. A dream villa for families and groups of friends seeking nature, tranquility and authenticity

Villa Hills on the horizon | Authentic Tuscan Style & Siena View

Siena, IT
4 Bedrooms 8 Guests
Aug 27 - 30
$1,478 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 4 rooms and 4 bathrooms, that can accommodate large groups of guests of up to 8 people. Our typical Tuscan Villa can be found just a few kilometers from the charming city of Siena. The Villa offers a splendid garden and a shared pool with a sunbathing and solarium area with comfortable loungers, as well as a large and spacious outdoor cover patio perfect for Al Fresco dining, WiFi and air conditioning. Bedroom 1: • King-size Bed with Fresh Sheets and Pillowcases • External Bathroom with Shower, Bathtub , Clean Towels & Complimentary Toiletries • Air conditioning • Free 24h Wi-Fi access Bedroom 2: • 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 3: • 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 4: • King-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 and armchairs that can accommodate up to 8 people. There are many windows that let in natural light. Al fresco dining External to the property you will find a table for al fresco dining for eight, a sofas and armchairs for complete your relax Terrace There’s direct access to a private covered terrace with an Amazing View on the Tuscany Hills and Siena 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

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

Independent Villa up to 18 guests Pool Tennis Fitness and Wellness area -VILLA GIUNCHETO

Monteroni d'Arbia, IT
9 Bedrooms 18 Guests
Sep 19 - Oct 3
$3,025 night

Independent residence (sleeps 18) composed of the main building and dependance. Main building sleeps 14 on the ground floor there is a large internal courtyard where it’s possible to eat outside, a dining room, a large living room with a fireplace, billiard table and CD player, a room with satellite TV, a large, fully equipped kitchen with a fireplace, oven, a fridge with an ice dispenser, a freezer and dishwasher, a toilet, a cellar in the basement. On the first floor there is large living room with a fireplace, computer, printer and fax, a double bedroom with en suite bathroom with bath, a double bedroom and en suite bathroom with shower and Turkish bath, a large double suite with a studio, dressing room and en suit bathroom with a hydro-massage bath, a double bedroom, a bathroom with bath, a double bedroom, two double bedrooms with a shared en suite bathroom with bath, a winter room with a fireplace. Dependance sleeps 4 with living room, kitchen, two double bedrooms with en suite bathroom with shower. Amenities Swimming pool (15 x 7.5mt), pizza oven, tennis court with a red-clay surface, five-a-side football pitch, bowls, gym and sauna 50mt away from the villa, parking, stereo in every room, internet connection, laundry. Next to the swimming pool there is a recently restored building with a kitchen, barbecue, a bathroom with shower and a stereo. Each bedroom has the air conditioning. Services on request: extra cleaning, catering, waiting staff, driver, and massages. The 35 hectare estate around the house produces olive oil and breeds cinta senese pigs. N.B. there is a very competent and helpful housekeeper who lives in a room on the ground floor. It is possible to rent the villa for a lower number of people, 14. Price upon request. Prices include consumption of water, gas, electricity (up to 300 kw), final cleaning, initial supply of linen for rooms and bathrooms (change of linen every 2/3 days), cleaning 4 hours in the morning, welcome dinner on arrival and consumption of air conditioning. The price does not include the consumption of electricity over 300 kw, the heating of the pool (€ 60 per day). On request: breakfast, lunch, dinner and cooking class. Upon arrival, customers will have to provide a security deposit of € 500.00 which will be returned to them at the end of the stay minus the cost of any damages incurred. Pets € 25.00 per week. Toddler bed € 30.00 per week. Extra bed € 80.00 per week. Check-in 3-7 pm | Check out 10 am. Open swimming pool 01 / 05-31 / 10 Upon arrival a tourist tax may be required according to the regulations of the municipality that hosts you. ***VILLA GIUNCHETO: Down Payment 30 % of the total ammount at the confirmation, balance 60 days before the arrival. Property Registration Number: IT052017B5FN97UTB3 Security Deposit of EUR500 to be collected upon arrival.

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

Sovicille, Tuscany, IT
6 Bedrooms 12 Guests
Aug 27 - 29
$2,225 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.

Il Fortino

Monteriggioni, Toscana, IT
2 Bedrooms 4 Guests
Sep 1 - 6
$132 night

This unique, 14th-century tower-house, set in pretty private gardens, complete with vines and looking out over the beautiful Tuscan countryside, sleeps 4 people. If you are looking for a romantic retreat, with masses of character, in the heart of the Chianti region, then this is the place for you. Arranged over three floors, this charming house has everything you need for a relaxing break, any time of year. A working fireplace in the living room will chase away any winter chills, whilst the shaded loggias will keep you cool in the summer. The spacious living room, on the raised ground floor, has a comfortable sofa and armchair. A traditional brick arch leads from the living room to the dining room with its painted wooden ceilings and bookcases. The wooden dining table seats 6. The newly renovated kitchen, with rustic tiling and wooden cupboards, is just off the dining room and is fully equipped with a cooker hob, oven, microwave, dishwasher, fridge, freezer and drip coffee machine. The master bedroom with a simple double bed and en suite bathroom is in the tower above the living area. Downstairs, on the lower ground floor, you will find a full-size pool table, which leads out onto the loggia. Adjoining this, separated by a screen, is the second bedroom, with 2 single beds and another en suite bathroom. The loggia is the ultimate in outdoor living space, furnished with a dining table seating 6 people, plus comfortable sofas for relaxing and admiring the views. There is also a TV and further tables and chairs, giving guests plenty of space to relax. For those in search of a more private area, there is a second, smaller loggia with four armchairs where you can read in peace or enjoy a cup of coffee looking out over the gardens. For sunbathing or an al fresco nap, there are 4 sun loungers just below the main loggia. In the garden, you will also find a special BBQ area and even a pizza oven, so you can cook like a local. Sleeping Bedroom 1: This pretty bedroom has a double bed, antique wooden cupboards and traditional Florentine chairs, plus an en suite bathroom. Bedroom 2: With two single beds, lots of books to read and its own en suite bathroom. Bathrooms Bathroom 1: En suite with the upstairs bedroom, this classic style bathroom is fitted with a glass shower, a washbasin, a bidet and a WC. Bathroom 2: En suite with the second bedroom, this shower room is tiled with traditional Tuscan stone tiles. It is fitted with a shower, a washbasin and a WC. Additional • No wifi • DVD player • Book library • Outside dining area • Pizza oven • Washing machine & laundry facilities • Smoke detector • Waste disposal • Hair dryer • Free parking available – a car is recommended for your stay • Extra child friendly • Please note that there are some added charges that the guests will need to pay on site. 1. A tourist tax of €2/Person/day for up to 4 days (Children below 12 years of age are exempt). 2. Heating with a pellet stove (cost based on pellet consumption). 3. Electricity has to be paid based on consumption at €0.35 kw/h. 4. Guests should pay a refundable security deposit of €200 on arrival. Location The house is in the heart of the Chianti hills, a 15-minute drive from the walled village of Monteriggioni, famous for its medieval fortifications. From here, you have easy access to Florence (1 hour 5 mins) and Siena (22 mins). The charming hill town of San Gimignano, with its many medieval towers, is definitely worth a visit (40 mins), and there are endless possibilities for visiting vineyards, fantastic local restaurants and markets. To escape into nature, there are many nature reserves in the area, including the nearby Parco Fluviale Alta Val D’Elsa (23 mins), which has some easy hiking trails and the stunning Diborrato waterfall, where you can swim in one of the river pools. For something more relaxing, visit the natural spa, the Terme di Petriolo (45 mins) for therapeutic mud treatments and thermal waters. If you are interested in wine, you can tour one of the many vineyards that surround Monteriggioni, where they make the famous local wine, Chianti Colle Senesi, and delicious extra virgin olive oil. Follow that up with lunch in one of the many excellent restaurants in the village. If you are inspired to cook at home and try out the pizza oven or BBQ, Monteriggioni’s weekly market, for local produce, takes place every Thursday and market day in Siena is Wednesday. You can find all other provisions in nearby Siena. The closest international airports are Florence (51 mins) and Pisa (1hr 25 mins)

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

Casale il Gualdo old stone house completely independent with an exclusive pool with Infinity edge -Casale il Gualdo

Radda in Chianti, IT
8 Bedrooms 16 Guests
Dec 12 - Jan 9
$1,659 night

Property for exclusive use Casale il Gualdo is an old stone house, completely independent, measuring 300 sq. m. and capable of holding up to 16 people with 8 double bedrooms and 6 bathrooms. The farmhouse, with an exclusive pool with Infinity edge, Wi-Fi, satellite TV and air conditioning, is perfect for groups of friends or large families. Outdoor area and swimming pool The farmhouse is surrounded by a large open area divided in smaller terraces with low stone walls, complete with tables and chairs for spending relaxing moments. The swimming pool, just a few metres from the house and accessible via a gate, is fenced off in a perfect position for admiring the surrounding woods and countryside. The pool is 11 metres by 6 with a depth of 1.5 metres and is surrounded by a bathing area with sunbeds, beach umbrellas and an outdoor shower. In front of the entrance you will find a charming pergola with tables and chairs, with a stone barbecue just a few metres away, making it ideal for outdoor meals and barbecues. The property also boast a small lake. There is parking in front of the farmhouse. Interior The house is characterized by traditional Tuscan elements like wood beams on the ceiling and cotto flooring. The main entrance leads to the living room with sofas and satellite TV, a dining room with a typical fireplace (which cannot be used) and three steps leading to the kitchen, which has outdoor access. Rounding up the ground floor are two double bedrooms, one bedroom with 2 beds, 2 bathrooms with shower, a small area with washing machine. Twelve steps down bring you to a double bedroom (with a ceiling height of 1.5-2.4 metres) with a bathroom with shower (4 steps up from the bedroom, ceiling 1.5-2 metres high). From the dining room, a staircase leads to the upper floor with a small living room with fireplace (which cannot be used) and sofa, a small kitchen ideal for making breakfast, a double bedroom with bathroom with shower, one bedroom with two beds (one of which is a ¾ bed, between a single and double bed) with bathroom with shower. Finally, this floor has another small living room with fireplace (which cannot be used) and sofas, two double bedrooms and one bathroom with shower. Location Casale il Gualdo is near Castellina in Chianti, an area filled with olive groves and vineyards. The location is very quiet and offers a great view of the surrounding landscape. Facilities The farmhouse has Wi-Fi, air conditioning in all the rooms, central heating, two baby beds, a high chair, complimentary toiletries and a hairdryer in every bathroom and parking in the property. Services The price includes: bathroom, bedroom and kitchen linen, as well as swimming towels (all changed weekly), 250 kW/h of electricity per week (extra consumption will be charged), internet, water and gas consumptions, baby bed and high chair. Upon request and to be paid for at the house are: cookery courses, dinners and tastings, hired help and babysitter. Charging for electric cars is available on request and to be paid upon consumption. Important Information The pool is open from May 1st to September 30th. Access to the house via 3.5 km of gravel road, not suitable for low cars. There is a keeper who discreetly takes care of the outdoor areas and the swimming pool and lives near the house in an independent position, maintaining your total privacy. It is not allowed to organize events of any kind (weddings, receptions, parties) unless previously agreed. Consequently, the number of people who will stay in the accommodation must not exceed the agreed number. It is forbidden to move the external and internal furnishings unless agreed with the property. The final cleaning does not include dishwashing and kitchen cleaning, which are the responsibility of the guests. Extra costs to be paid on the spot: -Tourist tax per person/day: 2,00 EUR -Final cleaning per booking in cash: 600,00 EUR -Refundable deposit (to be handed over on arrival) per booking in cash: 500,00 EUR -Electricity upon consumption above 250 kwh per week: 1,50 EUR -Heating per day: 100,00 EUR Activities and Distances The Chianti region is in the middle of Tuscany, between Florence, Siena and Arezzo and is perfect for discovering Tuscany’s history. Radda, Gaiole, Panzano are all near and can be reached via the “Strada Chiantigiana” where you can find great views. You can also reach the famous Tuscan towns and cities, full of art and culture, like Siena, Florence, Volterra, Arezzo and San Gimignano. 4.5 km Castellina in Chianti (small supermarket, shops, restaurants), 15 km Radda in Chianti, 23 km Gaiole in Chianti and Colle Val d’Elsa, 25 km Greve in Chianti, Monteriggioni and Poggibonsi, 28 km Siena, 35 km San Gimignano, 50 km Florence and Volterra. Food shops: Castellina in Chianti, 4.5 km Restaurant: Villa Casalecchi, 3 km Golf course: Circolo Golf dell’Ugolino, 40 km Airport: Firenze Peretola, 61 km Railway station: Castellina in Chianti-Monteriggioni, 15 km Shopping centre: Coop Valdelsa (Poggibonsi-SI), 19 km Property Registration Number: IT052023B5MFSKW6T9 Security Deposit of EUR500 to be collected upon arrival.

Casa Vedetta

Radda in Chianti, IT
7 Bedrooms 14 Guests
Aug 30 - Sep 3
$2,509 night

Casa Vedetta is located within a staggering 800-acre privately owned estate that has been settled for around a thousand years. This rural estate is made up of vast vineyards, oak forests and olive grounds where you can enjoy a peaceful escape from day-to-day life and head out on walks through the nearby hills before driving to picturesque villages for dinner.    The villa is set over three floors with plenty of space to accommodate 14 guests. The ground floor is the heart of the home, where everyone can gather together for breakfast before heading out for the day or a chat over evening drinks. The bright and airy living room retains the original wooden beams and open fireplace and has two large sofas; this room leads straight through to a formal dining room which can seat your whole party. You will find a sleek, modern kitchen with everything you could need to prepare dinner on the ground floor, while if you prefer to dine outdoors, you could use the covered woodfired pizza oven. If the kids would like a bit of space to play away from the adults, they could claim the first floor living room, which has a flat-screen TV and is close to the games room.   When night falls, you will have seven bedrooms to choose from. One of these rooms is set on the ground floor and is equipped with a disability-friendly bathroom. Another bedroom is on a mezzanine level, with a seating area and an en-suite bathroom. Two further en-suite double bedrooms can be found on the first floor, and the final three bedrooms are on the second floor.   As you step outside, you will find yourself in a manicured garden. The vast estate and vineyards surround the grounds, offering unspoilt views from everywhere around the house and garden. If you would like to treat yourself to an afternoon of pampering, why not swim in the inviting private pool before using the Turkish bath and the sauna in a spa area on the grounds. The stunning garden lends itself to outdoor living so guests can enjoy the lovely climate while dining al-fresco and unwinding on the poolside sun loungers.    If you would like to see more of the local area, you can visit the sleepy village of Lecchi in Chianti which is 5km away and an excellent spot for a wander around the historic streets and a coffee in the village square. For a wider range of shops, cafés and traditional Tuscan eateries, why not drive to Radda in Chianti, a hilltop town 8km from the home. Dotted around the verdant hills between the villages and towns of Chianti, guests will discover numerous family-run wineries and vineyards which produce famous Chianti wine. Many vineyards can be visited on a tour where guests will be taken around the production areas and vineyards and sample the wines, often accompanied by lunch.    Further afield, you could take a day trip to one of Tuscany’s best-loved cities, such as Florence and Siena. Florence is 62km away and is known for its museums and galleries, such as the world-class Uffizi Gallery. The breathtaking buildings of the Piazza del Duomo, the Ponte Vecchio bridge and the historic town hall are also well worth exploring. Florence is a beautiful city which is easily explored on foot, either independently or on a guided tour. Siena is closer to home at 32km away, smaller and less crowded. Siena’s medieval centre is incredible and leads from the Piazza del Campo. In this main square, you can enjoy dinner at a street-side restaurant with a view of the 14th-century Palazzo Pubblico and its imposing tower.  Features: Villa Interior Ground Floor - Living room with fireplace and two sofas- Dining room with dining table seating 12 guests- Fully-fitted kitchen with oven, hob, fridge freezer, dishwasher, microwave and coffee machine- Bedroom with two single beds and disability adapted en-suite bathroom with shower, sink and WC Mezzanine Level - Bedroom with double bed (160cm x 200cm), seating area, en-suite bathroom with shower, double sink, bidet and WC First Floor - Living room with sofas, piano and flatscreen TV- Games room- 2 x bedrooms with double beds (160cm x 200cm) and en-suite bathrooms with showers, double sinks, bidets and WCs Second Floor - 3x bedrooms with double beds (160cm x 200cm) and en-suite bathrooms with showers, double sinks, bidets and WCs Annexe - Spa area with sauna, shower and Turkish bath Outside Grounds - Private infinity pool with saltwater purifying system and pool lift (4m x 11m, max depth:1.4m)- Landscaped garden with lawns and trees - Covered outdoor living room- Outdoor sofas- Al-fresco dining terrace- Poolside sun loungers- Woodburning pizza oven- Barbecue - Vegetable garden- Parking Facilities  - Wi-Fi- Air-conditioning- Central heating- Smart TVs- Washing machine- Dryer- Board games - Hairdryers - Piano - Ice machine Location: If you are looking for somewhere to explore the villages and vineyards of Chianti in Tuscany, Casa Vedetta is a fantastic choice. When holidaying here, you can enjoy walks in the 800 acres of private land around the home and in the surrounding countryside, or you could visit a different hilltop village or town each day.    The house is located in a peaceful country setting where you can spend your days unwinding amongst the olive groves and fruit trees, with only the sound of the birds to be heard. You will also find a few pretty villages and towns within a 10km drive.    The closest village is a small settlement called Lecchi in Chianti, a mere 5km away. Lecchi is a good starting point for walks, hikes and days out cycling through the nearby hillside trails, which wind through ancient oak trees. You can also access natural spring pools in the forests, which are an excellent place to swim on a hot day. The village is almost 1000 years old and is a charming place to wander around; there are a few coffee shops here, a small supermarket and Monteluco castle, which the village was built around. Surrounding Lecchi in Chianti, several such castles were used as defensive fortresses in centuries gone by but are now mostly converted into private homes or wineries.    If you would like to see one of the medieval castles close up, you can drive the 4.5km to Castello di Ama. The Castello has Etruscan origins, although it was rebuilt in the 1700s along with some of the buildings of Ama village. Castello di Ama is now a vast vineyard where visitors can tour the vines and cellars and participate in wine tastings. There are impressive sculptures and installations created by world-renowned artists around the buildings, grounds and cellars.  For a large selection of shops and eateries, you can drive to Radda in Chianti, an authentically Tuscan hilltop town just 8km away, or Gaiole in Chianti, which is 14km away. Those looking to visit one of Tuscany’s cities can visit the gorgeous city of Siena, which is just 32km away or Florence, which is 62km away and is a hub for lovers of art. Both cities have unique characters and are packed with galleries, museums and awe-inspiring historic buildings.  Terms & Conditions: ? €1000 charged to client’s credit card as a pre-authorisation one month before arrival and refunded two weeks after departure, subject to full inspection. 4.00 p.m. 10.00 a.m. Yes. Yes. On request only and with prior agreement with the owner. Weddings and any special events are on request only and subject to prior arrangement with the owner and additional charges. This property has wheelchair access. However, please contact us before booking so we can discuss individual accessibility requirements with the owner to ensure that this property is suited to your specific needs. Flexible. Standard changeover clean included in the price. Guests are required to leave the accommodation clean, tidy and in the same condition as on their arrival. Any extra cleaning, laundry, maintenance and/or rubbish disposal required will be charged against the security deposit. Outside only. 4 nights. All other durations on request. Yes. Italian Visitors Tax payable locally in cash (typically costs €1-€10 per adult per night - please enquire if exact amount is required). Wi-Fi internet access included. Yes. Please note that pool opening dates are subject to local weather conditions and pool maintenance requirements and that cooler months may not be suitable for swimming. Licence number: IT052013B4ZVVOD2A2 CIR: 052013CAV0010

Spacious Convenient Villa with Heated Jacuzzi

Marcialla, IT
4 Bedrooms 8 Guests
Aug 27 - 31
$332 night

The spirit of Tuscan craftsmanship and rich Italian heritage runs through this resplendent countryside villa. A panoramic terrace and garden overlooks vineyards and olive groves; the richness of the region on full display. A private heated Jacuzzi and patio full of Italian greenery await outside a characterful, comfortable, and fully-modernized interior, with fine details, unparalleled comfort, and ancient sights nearby. VILLA CHIANTI’s destiny is to be a home where the past is respected and retained, while being updated with tasteful facilities that make a stay here a true pleasure. The restored rooms makes the most of exposed brick and heritage fixtures, flared with engaging visual art and framed prints. Naturally, the family-sized dining table is front and centre, set under shining lights and promising evenings of plentiful food and rich laughter. Guests can relax on the plush, cushioned suites, or experience blessed refreshment via the fine bathrooms and walk-in showers and tub. VILLA CHIANTI is conveniently located into one of the region’s most acclaimed wine district and close to one of the most famous Italian cities: Florence, situated just a short drive away. Local villages offer quiet cafes, family-run restaurants full of local delights and dishes, plus gelaterias and bakeries offering tasty treats. Local wineries will delight you with memorable wine tastings among the barrels in centuries-old cellars. Take to the lush country lanes for guided horse riding or relaxed bike rides, with majestic ruins of Villas and Churches beckoning to the hills by Florence. Most of Italy’s great cities and villages such as Volterra, Certaldo, San Gimignano, Greve in Chianti, Impruneta, Radda, Gaiole and Siena are a short drive from VILLA CHIANTI. The property is located at the ground floor of an ancient palace dating back to 1300s in the main square of the Chianti village of Marcialla. The apartment is on two floors. On the main floor the kitchen, the dining and living, a bedrooms with private patio and full bathroom. On the lower floor by the garden and pool there are 2 bedrooms and a full bathroom. The garden is accessible from both bedrooms through French windows and it features a kitchenette by the outdoor dining area. An hayloft with 1 bedroom and 1 bathroom is accessible from garden and from the hall of the building. Air conditioning, washer and clothes dryer, a fully equipped kitchen with microwave, toaster, American coffee maker, Nespresso machine, oven and a wide selection of cooking utensils and appliances is not missing. A baby cot is available (free of charge), on request. Please advise us if you will need it. Due to the thick historic stone walls, the Wi-Fi is reliable on the main floor and outdoors, but can be limited on the lower floor—the perfect excuse to unplug and relax. Please kindly note that the use of the Jacuzzi Pool is not allowed during the night. We recommend a proper use of the whirlpool, according the internal regulation that you will be requested to accept and sign on arrival. Please also take note that from September to May included heating the Jacuzzi involves an extra cost of Euro 25 per day. Chianti is one of the most beautiful and well-known areas of Tuscany. You will be surrounded by rolling hills and perched villages typical of the area between Florence and Siena, therefore we advise you to have a car available. Getting around by car can be really pleasant to savour its essence, experience its colours, scents and history. Parking free of charge, in the square in front of the house. Included in the rental price: Final Cleaning Towels and linens Electricity Gas Water Internet Wifi Not included in the rental price: Tourist tax: mandatory and required by the local municipality, where applicable. Midstay and/or weekly cleaning and change of towels and linens High chair (upon request at booking) Babycot (upon request at booking) Baby cot’s linens

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

Villa Santo Stefano up to 14 sleeps Pool-SANTO STEFANO

Monteroni d'Arbia, IT
7 Bedrooms 14 Guests
Nov 28 - Dec 26
$495 night

Accommodation Independent house 14 sleeps composed by 2 apartments Apartment Est 8 sleeps at the ground floor livingroom, a diningroom, kitchen with dishwasher and oven, a toilet. At the first floor a double bedroom, a twin bedroom, a bathroom with shower, a double bedroom, a twin bedroom, a bathroom with shower. Apartment Ovest 6 sleeps at the ground floor a livingroom, a diningroom, kitchen with dishwasher and oven, a double bedroom and a bathroom with shower. At the first floor a double bedroom, a twin bedroom, a bathroom with shower. Amenities Swimming pool (10x3.80 m) fenced with hedges and wooden fence in front of the entrance, internet connection, furnished garden, furnished portico with table and chairs, in the apartment Est a washingmachine, tv, barbecue, car parking. Possibility to add two single beds. Although part of the same property, the two accommodations are managed separately to ensure maximum privacy and tranquility: Hostel Guest Access: Guests of the hostel only have access to their designated areas, which are the reception and the paths leading to the main road. Private Villa Areas: Access to the private areas of the villas (such as gardens, terraces, swimming pools, etc.) is strictly prohibited for hostel guests and is solely reserved for guests staying in the villas. Management Commitment: Privacy and quiet are core values for the management. It is of fundamental importance to maintain a clear separation between these two environments (the hostel and the private villas), and all guests are expected to respect these rules Prices include consumption of water, gas, electricity, final cleaning, linen for rooms and bathrooms (linen change is weekly). Any consumption of air conditioning / heating is not included in the price and will be payable locally based on consumption. Upon arrival, customers will have to provide a security deposit of € 1000.00 which will be returned to them at the end of the stay minus the cost of any damages incurred. Animals € 70.00 per week. Baby cot € 30.00 per week. Extra bed € 70.00 per week in bed (up to 16 people) Tourist tax: €2 per person per night, to be paid on site. Check-in 3-7 pm | Check out 10 am Pool open 01 / 05-30 / 09 Heating not included: € 5,00 per mc Extra Cleaning: € 20,00/hour Surcharges for any parties/weddings in villa to be agreed according to period and number of people. ***VILLA SANTO STEFANO: down payment 30% of the total ammount at the confirmation Property Registration Number: IT052017B5QS5QAHJT Security Deposit of EUR1000 to be collected upon arrival.

Villa Gaiole

Radda in Chianti, IT
7 Bedrooms 14 Guests
Sep 4 - 9
$5,384 night

Offering panoramic vistas over Chianti’s rolling hills and woodlands, Villa Gaiole is a serene Tuscan retreat that sleeps up to 14 guests across seven luxurious bedrooms. This 400-year-old property, once a rustic farmhouse surrounded by vineyards and olive groves, has been beautifully restored to balance historic charm with modern comfort. The villa is divided between the main building and a smaller annexe, both full of character with exposed beams, stonework, and open fireplaces. Inside, you’ll find spacious, light-filled living areas thanks to vast floor-to-ceiling windows that frame the valley views. The ground floor is the social hub, with a welcoming lounge, a feature fireplace, a dining room, and a fully equipped kitchen—though catering packages with a private chef can also be arranged. Additional highlights include a wine cellar, games room, fully equipped gym, and a second sitting room, ensuring plenty of space for everyone. Each of the seven bedrooms is tastefully decorated and has its own en-suite bathroom. Six boast super king-sized beds, while one can be set up as a twin or double. Two of the bedrooms are housed in the annexe, perfect for families or guests who’d like a little extra privacy. Step outside to discover two hectares of gardens, olive groves, and vineyards. The heated infinity pool is the star attraction, complemented by numerous terraces, shaded dining spaces, and sun loungers ideal for lazy afternoons. The villa’s concierge team can arrange extras such as truffle hunting, pizza-making classes, yoga, or guided tours. Though wonderfully peaceful, Villa Gaiole is close to picturesque Chianti villages and only 28km from Siena, making it an excellent base for exploring Tuscany’s art, food, and medieval history. Villa Gaiole offers the perfect blend of tradition, elegance, and comfort for an unforgettable group holiday in Tuscany. Features: 10-person capacity: main villa only14-person capacity: main villa and annexe The Villa (800m2 over two floors) Ground Floor- Living room with sofas, desk fireplace and TV- Games room with seating area, pool table and football table- Dining room with table seating 14- Fully-fitted kitchen with breakfast bar- Guest WC- Gym and Wine cellar- Internal courtyard- Bedroom with super king-sized double bed, seating area an en-suite bathroom with shower (accessible from the courtyard) First Floor- Sitting room with bookshelves and TV- Bedroom with super king-sized double bed, seating area an en-suite bathroom with bath, double sink and WC- 2x bedroom with super king-sized double bed and en-suite bathroom with shower, sink and WC- Bedroom with twin beds or a super king-sized bed and en-suite bathroom with shower, sink and WC Annexe- 2x bedroom with super king-sized double bed, sofa bed(for up to two children) and en-suite bathroom with shower, sink and WC Outside Grounds (20,000m2) - Private heated swimming pool, with safety cover (12m x 6m, 1-3m deep) open approximately start of April- end of October- Two hectares of private grounds, olive groves and vineyards- Covered dining pergola- Al-fresco dining terrace- Wraparound terrace with outdoor sofas- Sun loungers and deck chairs - Barbecue- Pizza oven- Parking Facilities  - Wi-Fi- Air-conditioning- Underfloor heating- Home office - TVs- Sound system- Film projector- Iron and ironing board - Gym equipment - Pool table- Football table- Board games and toys Extra Sustainability Gems About the Property The owners have installed solar panels and a wood pellet burner for hot water, as well as their our own fresh water well (natural and treated) which they encourage guests to use as opposed to buying plastic bottles of water.  Location: Villa Gaiole boasts an enviable position overlooking the rolling hills of Chianti, immersing guests in one of Tuscany’s most iconic landscapes. Scenic walking trails, medieval hamlets, vineyards, and olive groves lie on the doorstep, perfect for countryside exploration at your own pace. Wine enthusiasts can enjoy tastings at local farms or tours at nearby wineries, while food lovers will relish dining in rustic trattorias dotted throughout picturesque villages. Just 5km away, Gaiole in Chianti is a charming spot often ranked among Europe’s best places to live. Its rich history includes a number of castles—some now wineries, others open to the public—and a long tradition of ceramics. Lecchi in Chianti, 6km away, offers shops, cafés, and traditional eateries for an authentic experience. Radda in Chianti, 12km away, provides a wider array of restaurants and shops. Once the headquarters of the Chianti League in the 15th century, this town enchants with winding medieval streets and historic landmarks such as the Palazzo dei Podestà and the Church of San Niccolò. For a longer excursion, Siena lies just 28km from the villa. A medieval jewel, the city is packed with art galleries, museums, and iconic sights, including the Duomo di Siena and the Palazzo Pubblico. Its lively piazzas and rich café culture make it a must-see for visitors seeking Tuscany’s history and charm. Terms & Conditions: ? An Accidental Damage Waiver of EUR 199 will be added to each booking to protect guests for up to EUR 2,500 in accidental damages at the villa. The waiver provides a limited damage cover in case of any damage to the property or its contents (except in the case of deliberate or reckless acts) up to the value of €2,500. It is essential to report any damage during your stay for the waiver to apply. For damages of a value which is above EUR 2,500 guests will be asked to pay based upon the value of the damage caused. 4.00 p.m. Check-in outside this time may be subject to an extra cost. Please enquire for more details. 10.00 a.m. Yes. Yes, with mid-week linen change for one-week stays. Pets are not allowed. Please note home security devices may be installed at the villa, please enquire for further information. Please note that your booking will only be confirmed once we have checked availability with the owner or their property manager. Please note that published rates are only valid for the current year. Any bookings for subsequent years will be on request only and correct rates will be confirmed at the time of booking. Please note that the use of any external caterers and/or contractors is not permitted. Flexible. Standard changeover clean included in the price, applicable for stays of 7 nights. Guests are required to leave the accommodation clean, tidy and in the same condition as on their arrival. Any extra cleaning, laundry, maintenance and/or rubbish disposal required will be charged against the security deposit. Outside only. 7 nights from mid-June to mid-August. 4 nights between January to April and October to December. 5 nights in all other periods. Estimated cost will be provided based on the week booked. Please enquire for exact amount, payable locally. Included from mid-April to mid-October, and at an extra cost for the low season (October to mid-April), payable locally. Please note that like all heated pools, pool heating and water temperature are reliant on weather and outside temperatures. Italian Visitors Tax payable locally in cash (typically costs €1-€10 per person per night- please enquire if exact amount is required). The pool is open approximately April to end-October. Please note that pool opening dates are subject to local weather conditions and pool maintenance requirements and that cooler months may not be suitable for swimming. Licence number: IT052013B4ARQLP4UZ / 052013CAV0037

Casalunga beautiful farmhouse with swimming pool and garden-CASALUNGA

Buonconvento, IT
6 Bedrooms 13 Guests
Nov 28 - Dec 26
$210 night

A lovely, well furnished house (sleeps 13) consisting of two apartments connected by external staircase, surrounded by fields of sunflowers in a quiet, peaceful location between Buonconvento and Monteroni d’Arbia, a few kilometers from Siena. Girasole from 8 beds on the first floor consists of a living room with fireplace (decorative only), TV, fridge, three double bedrooms, one twin bedroom, two bathrooms with shower. External loggia. Stalla for 5 people on the ground floor consists of a large living room with table seating 12, music and mp3 player, living room with fireplace and TV, large kitchen with microwave and dishwasher, kettle, a double bedroom with third bed, a small bathroom with shower, a bedroom matrimonial. In front of the house a large covered patio with a table for 16 people. Services Enclosed semi-enclosed pool (9 x 4.5 m - depth 1.50 m) outdoor equipped green space, parking in front of the house, , built-in barbecue, free wi-fi internet connection, mosquito nets (rooms), washing machine. On request Beautician, home cook, maid for cleaning and ironing in the house, tour guide Siena and surroundings. Prices include water, gas, final cleaning, linen for rooms and bathrooms (linen change is weekly). Any heating consumption is not included in the price and will be payable locally based on consumption (60€ per day) Upon arrival, customers will have to provide a security deposit of € 500.00 which will be returned to them at the end of the stay minus the cost of any damages incurred. Pets € 30.00 per week. Baby cot € 20.00 per week. Extra bed € 80.00 per week. Check-in 3-7 pm | Check out 09 am. Swimming pool: Open from May to September, weather permitting. The house does not have outdoor car charging stations and does not have a facility suitable for charging with the home system. Information for the nearest charging stations will be provided if needed. Upon arrival a tourist tax may be required according to the regulations of the municipality that hosts you. Property Registration Number: IT052003B4XJWJ3EPS Security Deposit of EUR500 to be collected upon arrival.

La Pieve Di San Martino - APT Girasole

Colle Val d'Elsa, Toscana, IT
1 Bedrooms 4 Guests
Aug 30 - Sep 1
$125 night

Relax and reset at this gorgeous countryside escape for 4 surrounded by vineyards, olive groves, and cypress-lined landscapes. Features a private terrace for alfresco mealtimes, a shared pool, BBQ and plenty of outdoor space. The ideal base to discover the magic of the Tuscan countryside, the property is one of 4 apartments in a historic townhouse just outside the village of Pian dell’Olmino. Nestled in the rolling hills between Siena (a 35-minute drive) and Florence (a 1-hour drive), the property provides easy access to many of Tuscany’s historic towns and wineries of the wider Chianti region. The apartment is situated on the ground floor and enjoys direct access to a private panoramic terrace that’s furnished with a table, chairs, and an umbrella. The perfect setting for a slow breakfast, an evening aperitivo, or a quiet night under the stars. There’s also a shared swimming pool with countryside views, a BBQ and a garden that’s ideal for reading, sunbathing, or unwinding. The property’s characterful, air-conditioned interior features many original features, including a cool terracotta tiled floor, rustic wood-beamed ceiling, and exposed stone walls. Guests can relax in the cosy living room, furnished with a sofa bed and a flat-screen TV, and featuring floor-to-ceiling windows that open onto the shared terrace and garden. The separate, eat-in kitchen is fitted with a dining table, a Moka coffee machine, an oven and a Cooker Hob. This space overlooks the pool and enjoys direct access to a private terrace. Outside, there’s also a laundry room with shared washing machines (near the pool). Sleeping Bedroom 1: The quiet, light-filled ensuite bedroom is furnished with a double bed and a wardrobe and luggage storage make it ideal for longer stays. Extra: There is also a double sofa bed in the living room Bathrooms Bathroom 1: The ensuite bathroom is fitted with a shower, a bidet, a washbasin and a WC Additional • Honeymoon Suite • Private Terrace • Shared Outdoor Pool (available from May 1st to October 1st) • Outdoor Shared Dining • Shared Garden • Shared Terrace • Shared BBQ • Airconditioning • Washing Machine (Shared) • Paid Laundry Facilities • Free Wi-Fl • Laptop Friendly Workspace • Central Heating • Fireplace • Car Recomnended • Private Parking Space • Free Public Parking • Child Friendly • Suitable for Elderly • Pets Allowed • Smoking Prohibited Extra Charges & Information: Tourist tax: €2.00 per person per night (max 5 days, children under 12 exempt) Minimum stay: 3 nights (April/May/October/November), 5 nights (June/July/August/September) Direct booking: 30% deposit required at booking, balance due 10 days before check-in Cancellation policy: 30% for cancellations over 30 days, 50% for 16-29 days, 90% for 7-15 days, 100% for less than 7 days or no-show Optional extras: Available on request through local partners: Tuscan breakfast delivered to your door · Poolside aperitivo · Special dinners & pizza nights · Birthday cakes · Wine tasting tours · Val d’Elsa biketours · Professional photo shoot on the estate · Local wine selection available to purchase The entire property can also be reserved exclusively for small events, intimate ceremonies, or private gatherings. Location: The apartment is nestled in the tranquil Tuscan countryside, just outside the village of Pian dell’Olmino within the breathtaking landscapes of the wider Chianti region. Siena is a 35-minute drive, Florence is a 1-hour drive, and San Gimignano is just a 15-minute drive away. Visitors can enjoy wine tasting, olive oil farms, scenic walks, cycling routes, and authentic Tuscan cuisine in the surrounding countryside. The closest winery is just a 5-minute drive away, with many more within a 10-15 minute drive from the accommodation. Nature lovers will enjoy the forested trails of Parco Fluviale Alta Val D’Elsa, which follow a stretch of river renowned for its turquoise colour and picturesque swimming spots. There are several restaurants within a 5-minute drive and a grocery store within a 10-minute drive. The closest international airport is Florence Airport (FLR), approximately a 50–60 minute drive away.

Villa Piandolce - Radda In Chianti

SI, Tuscany, IT
6 Bedrooms 12 Guests
Aug 29 - Sep 5
$5,540 night

VILLA PIANDOLCE - RADDA IN CHIANTI - SIENA AREA The property offers all modern technology and comforts. In the immediate area of the town of Radda, guests can easily explore the unique regions of Florence, Siena, San Gimignano, and Chianti or relax at the villa, enjoying wine tastings, the gym, and the wellness area around the private pool. The villa combines modern comforts with preserved historic features and original materials. You’ll find archways, vaulted ceilings, irregular stone walls, and large windows that illuminate the interior and offer views of the surrounding hills, all contributing to an atmosphere of peace and tranquillity. Outside the villa is a patio equipped with a BBQ, pizza oven, and an "al fresco" dining area. This part also features a garden area with a private heated swimming pool (open from 1 April to 1 November), umbrellas, deck chairs, and children’s games. On the opposite side of the villa, there’s a delightful gazebo furnished with tables and chairs, perfect for enjoying breakfast or dinner in serene surroundings. Inside, the villa has three levels: a lower floor, a ground floor, and a first floor, which is served by an elevator. On the lower floor, you will have a wine cellar with a selection of wines for sale, a gym room (with weights, rower, cyclist, yoga equipment, TV), a Wellness area with its Turkish bath, basin and shower and two bathrooms: one with the bathtub and one with shower. To complete the layout there is an equipped laundry with washing machine and dryer. On the ground floor, there is a sitting room with two divans and two armchairs, TV and fireplace, a dining room, TV SAT, mobile bar, a professional kitchen, table and TV, a bedroom with two single beds, and a separate guest bathroom. On the first floor, you have a sitting room with divans, armchairs, a smart TV and a fireplace, a bar with glasses, a wine fridge, an ice maker, and a little fridge. The sleeping area consists of 5 double bedrooms with ensuite bathroom equipped with shower. The villa also comprises an annexe on the ground floor with a double bedroom, kitchen, en-suite bathroom, living room, TV, fireplace. Sleeps 12 TU1046 Amenities: EV Charge Point, Heated swimming pool, Outdoor seating, Parking, Ping pong table, Blender, Coffee maker, Dishwasher, Fridge with ice maker, Fruit juicer, Microwave, Oven, Toaster, Water boiler, Wi -Fi, Air conditioning, Clothes-dryer, Courtesy line in each bathroom, Elevator, Fireplace, Garage, Hairdryers in all bathrooms, Heating, Iron and ironing table, Mosquito screens, Alarm system, Emergency first aid kit, Fenced property, Fire extinguisher, DVD player, Stereo HI FI Bluetooth, Laundry, Pool and bath towels, Bed linens, BBQ, Pizza Oven, Children Playground. Included in price: - Welcome dinner light welcome dinner on Monday, Wine tasting wine in our cellar (Wednesday 14:30) - Continental buffet breakfast served indoor or outdoor except on Sunday - Daily cleaning included (5hrs/6 days per week - no Sunday) Distances: Nearest shops and restaurants: Radda in Chianti 1,5km Nearest towns: Radda in Chianti 1,5km, Gaiole in Chianti 6km, Castellina in Chianti 14km Nearest airport: Florence 64km, Pisa 103km Things to do: - Castello di Brolio: a stunning castle surrounded by vineyards, home to the famous Barone Ricasoli winery, and offering panoramic views of Chianti. - Siena: a must-visit city for its Piazza del Campo, the majestic Siena Cathedral, and the historic Palio horse race. - San Gimignano: famous for its medieval towers, historic center, and world-renowned gelato.

Vacation Rentals in Siena by Amenities & Features

More space, more privacy, more points with every home rental.

What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near Siena

Saved Home Image
Sign in or join now to view and save the homes you love