Pet-friendly vacation rentals in Siena, Italy

Explore 150 pet-friendly vacation rentals, homes, and villas in Siena for your next getaway or business trip. Bring your pet along and enjoy the comfort and privacy of a home with premium amenities such as Air Condition Homes, Homes with Pools and Homes with Free Parking. Throughout your stay, settle in together, enjoy more space to relax, and experience your destination side by side. 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 stay personalized for your taste. 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 pet-friendly adventure and enjoy the journey together.

150 Pet-Friendly Homes in Siena

Casina Di Giada

Siena, Toscana, IT
2 Bedrooms 4 Guests
Aug 24 - 27
$135 night

A modern retreat to soak up the historic heart of Siena! Nestled in the charming historic centre of the medieval city of Siena, this 2-bedroom holiday apartment easily accommodates up to 4 guests. The ground-floor apartment is just a stone’s throw from the famous Il Campo square of Siena and provides you with every modern comfort for a self-sufficient holiday. Inside, the apartment offers an open-plan living room with dining and a fully-fitted kitchenette where you can effortlessly cook meals. A dishwasher, microwave, oven, induction hob and fridge with freezer are available. The apartment also offers Wi-Fi, a Smart TV and waste disposal. Sleeping Bedroom 1: An elegant double bedroom with lounging and wardrobe storage. Bedroom 2: A bedroom with an en-suite WC, 2 single beds and a wardrobe. Bathroom Bathroom 1: The full bathroom features a shower, WC and bidet. Ensuite to bedroom 2, there is a WC for added convenience. Additional • Free Wi-Fi • Central Heating • Waste Diposal • Smart TV • Hair Dryer • Car not necessary • Pets Allowed • Paid Public Parking Extra Charges Tourist tax is 2€/person/night for the first 4 days (guests below the age of 12 are exempt) and an RSD (Refundable Security Deposit) of € 100 must be paid in cash upon arrival at check-in. Please note: Check-in time is from 4-8 pm and Check-out time is from 8-10 am. Any other check-in/out time has to be previously agreed upon. The apartment is located in the historical centre in a pedestrian area not accessible to private cars. However, within a radius of 400 metres, there are 2 large public car parking. Location The apartment’s location places you right in the heart of all action in Siena. Among the must-visit attractions, the iconic Siena Cathedral stands out, as a UNESCO World Heritage site, and the Piazza del Campo, the vibrant heart of Siena with several attractions like Palazzo Pubblico with the Civic Museum, which is only a 5-minute walk from the apartment. From your convenient location, many restaurants and a supermarket are also within walking distance. Guests can also explore the famous medieval walled city of Monteriggioni and the hills and villages of the Chianti "Gallo Nero" such as Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, and Panzano in Chianti in under an hour’s car journey from here. For famous touristy spots, a visit to Florence takes about an hour’s drive from here. The nearest international airport is also in Florence.

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

Romantic Apartment In Chianti Classico

Castelnuovo Berardenga, Toscana, IT
1 Bedrooms 2 Guests
Aug 31 - Sep 2
$76 night

Explore the Chianti hills and vineyards from this Apartment for 2 in the heart of Tuscany. On the first floor of a traditional stone house in a small village, the apartment can sleep 2 people and makes an ideal getaway for a couple who wants to get to know this picturesque part of Italy. The entrance is via a flight of stone stairs which leads to a communal balcony and then the front door. The brightly painted living area is divided into 2 parts. On one side is the kitchen/diner and on the other the sitting room. The modern open kitchen is equipped with an induction hob, microwave, dishwasher, a Dolcegusto coffee maker, electric kettle and a fridge/freezer. The dining table can seat 4 people. Guests can relax on the comfortable sofa in the sitting room and watch TV. Sleeping The cosy bedroom has a painted beamed ceiling and is furnished with a double bed and a wardrobe. Bathroom The cute bathroom is appointed with a shower, basin, bidet and WC. Additional - Free Wi-Fi - Smart TV - Air conditioning - Heating - Smoke and CO detectors - Hairdryer - Suitable for children (cot and high chair available) - Small pets allowed - Bike storage room - Free public parking near the house (no parking in the village) - €300.00 security deposit by credit card for guests under 21 years of age - Check-in from 4pm, check-out by 10am. €150.00 security deposit by credit card is required. Any damages or extraordinary cleaning costs (such as uncollected rubbish, unwashed dishes, etc.) will be deducted from the deposit. Location The apartment is wonderfully located in the heart of Chianti. It is the ideal base for guests to explore the vineyards of the region and try the world-famous local wines. Castellina in Chianti (12 minute drive); Gaiole e Radda in Chianti (25 minutes); Panzano in Chianti (38 minutes) and Greve in Chianti (48 minutes). It goes without saying that guests will find a wide range of vineyards and cellars that offer wine tasting, as well as a range of restaurants serving typical Tuscan cuisine. Some of Italy’s most beautiful cities and villages are within easy reach. Florence, (1 hour and 15 minutes) offers some of the finest galleries, museums and architecture in the world. As do Siena (30 minutes) and San Gimignano (1 hour), famous for its many towers. Siena’s Palio takes place on 2nd July and 16th August. Visitors can experience the excitement of this Medieval horse race around the picturesque Piazza del Campo. For self-catering, the local markets are a treasure trove of the very best local produce, from vegetables to cheese and olive oil. Siena’s weekly market (Wednesday) is one of the largest in the area, there is also a smaller one on Friday mornings. The closest airport is Florence Peretola, a 1 hour and 15-minute drive.

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

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.

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

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

Luxury Apartment in Prime Location, Tuscany Apartment 1002

Tuscany, IT
2 Bedrooms 4 Guests
Sep 22 - 26
$174 night

Property Manager is proud to present Tuscany Apartment 1002. ’Tuscany Apartment 1002’, 3-room apartment 85 m2, on the ground floor. Beautiful and tasteful furnishings: livingdining room with open-hearth fireplace and satellite TV. Exit to the garden, to the terrace. 1 double bedroom. 1 double bedroom. Exit to the garden. Kitchenette (4 hot plates, mini-oven, electric coffee machine). 2 showersbidetWC. Terrace, small garden, lawn. Terrace furniture, barbecue. Facilities: Internet (WiFi, extra). 1 pet dog allowed.Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property there is the stone house which consists of 2 parts and the owner’s farmhouse.Rustic tuscan furniture. Automatic gate. Swimming-towels available for the clients (extra). Farmhouse ’La Mirandola’, renovated. 10 km from the centre of Castellina in Chianti, 15 km from the centre of Siena, 45 km from the centre of Firenze, in a quiet position, in the countryside. For shared use: property (fenced), large, beautiful, well-kept garden with lawn and plants, swimming pool (14 x 7 m, depth 140 - 200 cm, 24.04.-16.10.). Table tennis, terrace, garden furniture. Private: terrace, garden furniture, barbecue. In the house: breakfast room, internet access (all extra), central heating system, washing machine (for shared use, extra), heating to be paid on the spot, heating available only from 01.11. to 15.04.. Room cleaning on request (extra). Breakfast possible. Roofed, parking at the house. Shop 2 km, railway station ’Castellina Scalo’ 2 km. Golf course 15 km, tennis 3 km, riding stable 2 km. Please note: the owner lives on the same property.

L’Oliveta at Montebuoni

Gaiole in Chianti, IT
2 Bedrooms 4 Guests
Sep 19 - 23
$263 night

Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a wine and olive oil estate, its original stone buildings have been carefully restored into attractive holiday homes and apartments. Set along the crest of a gently rolling hill, Montebuoni enjoys sweeping, postcard-perfect views across vineyards and countryside in every direction. The peaceful setting and natural beauty create an atmosphere that invites you to slow down and unwind. Guests can enjoy a shared pool, a separate children’s pool, and a tennis court, with tennis rackets provided.The hamlet is car free, with parking at the entrance, which adds to its relaxed, village-like character. The picturesque village of Lecchi is just 1.5 km away and can be reached on foot via a well-maintained, gently hilly path. Here you will find the excellent Ristorante Malborghetto and a small grocery shop. Another charming village within walking distance is San Sano. The medieval town of Radda in Chianti, with shops and good restaurants, lies about 8 km away. Surrounded by the Chianti Classico wine region, Montebuoni is close to renowned wineries such as Castello di Ama and Castello di Brolio. Siena, Arezzo and Florence are all great options for memorable day trips. About the villa L’Oliveta is a cosy detached cottage with its own private garden and a spacious terrace shaded by a pergola. Surrounded by scented plants and olive groves, it is perfect for relaxed alfresco meals or unwinding with a chilled drink and a good book. A plunge pool offers welcome refreshment, while beautiful views stretch across vineyards and the gentle Chianti hills. Inside, wooden beamed ceilings, terracotta floors and tasteful, comfortable furnishings create a warm and inviting atmosphere. Ground Floor Kitchen Fully equipped kitchen, small fridge/freezer, gas hob. Diner with Lounge Dining table, sofas, wood burning stove, TV Bedroom 1 Double bed (cannot be converted into twin beds), wardrobe, chest of drawers. Bedroom 2 Pair of twin beds (cannot be converted into a double bed), wardrobe, chest of drawers. Bathroom Shower, sink, WC. Shared Pool Length: 15 metres Width: 7.5 metres Depth: 1.5 metres Entrance: Roman steps Opening times: April to October Fenced: Yes Furnished: Sunloungers and parasols Cleansed: Chlorine Distance from villa: 100 metres Tennis Court Surface: Astro-turf Playing equipment: Provided Distance from villa: 150 metres 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: Public, onsite parking

La Vigna at Montebuoni

Gaiole in Chianti, IT
2 Bedrooms 4 Guests
Sep 8 - 12
$255 night

Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a wine and olive oil estate, its original stone buildings have been carefully restored into attractive holiday homes and apartments. Set along the crest of a gently rolling hill, Montebuoni enjoys sweeping, postcard-perfect views across vineyards and countryside in every direction. The peaceful setting and natural beauty create an atmosphere that invites you to slow down and unwind. Guests can enjoy a shared pool, a separate children’s pool, and a tennis court, with tennis rackets provided.The hamlet is car free, with parking at the entrance, which adds to its relaxed, village-like character. The picturesque village of Lecchi is just 1.5 km away and can be reached on foot via a well-maintained, gently hilly path. Here you will find the excellent Ristorante Malborghetto and a small grocery shop. Another charming village within walking distance is San Sano. The medieval town of Radda in Chianti, with shops and good restaurants, lies about 8 km away. Surrounded by the Chianti Classico wine region, Montebuoni is close to renowned wineries such as Castello di Ama and Castello di Brolio. Siena, Arezzo and Florence are all great options for memorable day trips. About the villa La Vigna is a beautiful semi-detached cottage with its own private garden and a spacious dining terrace, perfect for enjoying meals outdoors or relaxing with a chilled drink and a good book, surrounded by scented plants and olive groves. A private hot tub adds an extra touch of comfort. Inside, white-painted wooden beamed ceilings, terracotta floors and comfortable furnishings create a bright and welcoming atmosphere. Ground Floor Kitchen Diner Fully equipped kitchen,fridge/freezer, gas hob, dining table, spiral stairs. Lounge Double sofas, open fire place, TV First Floor Bedroom 1 Double bed (can be converted into twins), wardrobe, armchair, air-conditioning, Bathroom Shower, sink, WC. Bedroom 2 Double bed (can be converted into twins), wardrobe, armchair, air-conditioning. Shared Pool Length: 15 metres Width: 7.5 metres Depth: 1.5 metres Entrance: Roman steps Opening times: April to October Fenced: Yes Furnished: Sunloungers and parasols Cleansed: Chlorine Distance from villa: 100 metres Tennis Court Surface: Astro-turf Playing equipment: Provided Distance from villa: 150 metres 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, Heating Hot Tub Arrival guide Approach road: Unpaved, even Parking: Public, 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

The Ultimate Apartment in the Perfect Location, Tuscany Apartment 1007

Tuscany, IT
1 Bedrooms 2 Guests
Nov 25 - 28
$168 night

Property Manager is proud to present Tuscany Apartment 1007. ’Tuscany Apartment 1007’, 2-room apartment 45 m2, on the ground floor. Rustic and cosy furnishings: living room with dining table, TV and radio. Exit to the terrace. 1 room with 1 french bed (160 cm), showerWC. Kitchenette (mini-oven, 4 gas rings, toaster, electric coffee machine). Gas heating. Comfortable furnishings in the country house style. Small terrace roofed. Terrace furniture. Beautiful view of the garden and the countryside. Facilities: children’s high chair, baby cot. Internet (WiFi). Please note: non-smokers only. Maximum 1 pet dog allowed. Private entrance.Beautiful on a vinyard country house ’Cellole’, detached, surrounded by trees and vineyards. 6 apartments in the residence. 2.5 km from the centre of Castellina in Chianti, 11 km from the centre of Radda in Chianti, outside the resort, 17 km from the centre of Siena, in an elevated position on a slope, 92 km from the sea, in the countryside. For shared use: property 11 ha with plants and trees, swimming pool (12 x 6 m, depth 120 - 220 cm, 15.04.-31.10.). ShowerWC in the pool area, pergola, terrace, garden furniture, barbecue. In the complex: reception, WiFi, washing machine (extra) (for shared use, extra). Motor access (150 m via unmade road). Parking on the premises. Supermarket 2.5 km, railway station ’Poggibonsi’ 14 km, sandy beach ’Marina di Bibbona’ 92 km. Nearby attractions: Monteriggioni 10 km, Wine area Chianti Classico 10 m. Local sale of farm products. Please note: the owner has a dog.

Casacorvo Minore at Borgo Gaiole

Gaiole in Chianti, IT
1 Bedrooms 2 Guests
Aug 30 - Sep 3
$157 night

Overlooking the lively Chianti town of Gaiole, Borgo Gaiole is a spacious and carefully maintained estate with around 40 holiday accommodations, built in the traditional Tuscan style using natural stone and terracotta. The communal pathways and courtyards are thoughtfully cared for and decorated with flowering plants, creating a welcoming and relaxed atmosphere throughout the property. A covered car park on the lower level adds convenience, with both stairs and a lift leading up to the central courtyard. One of the highlights is the large shared swimming pool, designed in an elegant mezzaluna shape and measuring up to 25 metres at its longest point, ideal for swimming, cooling off and relaxing by the water. A fitness room is also available for guests to use during their stay. The centre of Gaiole can be reached on foot in less than ten minutes and offers a good selection of shops, a Coop supermarket, cafés and excellent restaurants. The town is well known for the annual vintage cycling event L’Eroica and is an appealing base for exploring the surrounding countryside by bike, with cycle hire available locally. Set in the heart of the Chianti Classico, the area is rich in renowned wineries, charming medieval villages and scenic landscapes. Siena, Arezzo and Florence are all within easy reach for rewarding day trips. About the villa Casacorvo Minore is a welcoming first floor holiday apartment with traditional wooden beamed ceilings and terracotta floors. It is comfortably furnished and offers a warm atmosphere. The pretty terrace garden with flowering plants and olive trees overlooks Gaiole and the Chianti hills and is furnished with a table and chairs for outdoor dining. First Floor Kitchen/ Diner/ Lounge Fully equipped kitchen with electric hob, fridge/ freezer, dining table, chairs, side table, sofa, armchair, coffee table, sat TV, air-conditioning, book-shelf, French door to two terraces, terraces with table and chairs. Bedroom 1 Double bed (cannot be converted into twin beds), bedside tables, armchair, wardrobe, chest of drawers, air-conditioning. Bathroom Bath with shower attachment, sink, bidet, WC. Laundry room (communal) Washing machine,dryer. Gym (communal) Well-equipped with bicycle and rowing machines, weights. Shared Pool Length: 27 metres Width: 9 metres Depth: 1.3 metres Entrance: Metal ladder Opening times: Easter to October Fenced: Yes Furnished: Sunloungers and parasols Cleansed: Chlorine Distance from villa: 20 - 40 metres The area is surrounded by various villas, which look onto the pool. From the pool there are pretty views over the roof tops onto Gaiole and the Chianti hills beyond the town. There is a small gym with showers available for guests and residents to use. 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: Paved Parking: Public, onsite parking

Large beautiful villa in Tuscan Hills of Chianti Stunning gardens and large pool

Tuscany, Toscana, IT
9 Bedrooms 18 Guests
Aug 24 - 29
$6,063 night

Don’t miss the  Chianti Classico, a luxurious Tuscany countryside retreat nestled among the beautiful  hills of Chianti. Wander in a private woodland, stroll  wildflower meadows, or take a dip in the 9-metre outdoor pool. With lavish interiors and many hidden treasures, The villa of Chianti Classico offers a magical experience around every corner. The villa has belonged to the same family for more than a hundred years, and has recently been artfully decorated by Princess Marianita Ruspoli in an elegant and timeless style with antique furnishings, oil paintings, porcelains and luxury fabrics in peaceful shades of whites, beiges, light blues and reds. As the villa sleeps up to eighteen guests and four staff, it makes the perfect accommodation for a large group of friends or family, looking to discover all that Tuscany has to offer in a unique and luxurious historic setting. The villa’s extensive private garden is a lovely space for the whole family to enjoy. The terrace seating overlooks breathtaking views, perfect for savouring your morning coffee or sipping a cocktail while viewing a stunning Tuscan sunset. Whether you’re looking for a weekend escape, a romantic retreat, or a family holiday, this historic Tuscan villa is the perfect oasis for creating unforgettable memories. The villa is equipped with all modern amenities, including plasma TVs with satellite channels, Netflix and DVD/Blu-Ray players, Wi-Fi, central heating and working fireplaces, washing machine and dishwasher, luxury tableware, and even exercise equipment. On request, we can arrange for you to experience Tuscany’s legendary flavors any way you wish! Our chef can come and cook you a lunch or dinner using the best local ingredients, or provide a lesson on real Italian-style cooking one evening. We can take you to the local organic shop to do the food shopping for the week, or you can ask for a cook to take care of the meals for the whole duration of your stay. Finally, don’t forget to ask about arranging a private wine-tasting to find the perfect accompaniment for your meals! At Chianti, Classico we offer additional services and experiences, including a tour of the Chianti Classico Gallo Nero wine cellars, Tuscan cookery classes, bird-watching in the tree house, outdoor drawing and painting classes, and much more. Located just a short drive from Florence and Siena and surrounded by our beautiful private wine estate, which includes Chianti cellars and olive groves, Villa Castellina in Chianti is the perfect place to relax and experience the beauty of Tuscany. Book now and indulge in the luxury of a boutique hotel combined with the flexibility of a private home. Please Note: This property includes access to a private chef (available at an additional cost). For privacy and security reasons, outside chef or catering services are not permitted. Property Registration Number: IT052005C2SYPIZD6L

Casino di Vescine

Radda in Chianti, IT
4 Bedrooms 6 Guests
Sep 26 - Oct 1
$588 night

Casino di Vescine is a charming Chianti country house in a peaceful, private setting surrounded by olive groves and the gentle green hills of the region. This traditional Tuscan property offers the ideal space for a relaxing holiday with family or friends. The large, well-maintained garden is dotted with mature trees, flowering plants, and inviting corners for dining and lounging outdoors. A particular highlight is the fenced swimming pool, making it especially suitable for families with young children. Located in the heart of the Chianti Classico, the villa provides easy access to the region’s renowned wineries and castles as well as its historic towns and villages. Radda in Chianti is only a 10-minute drive away and offers restaurants, shops, and all essential services. Castellina in Chianti is also within easy reach, and we recommend stopping for an artisanal ice cream at the Gelateria di Castellina. A good local restaurant can be found just 1.5 km from the house. The stone-built farmhouse is arranged over two floors and features a large covered terrace, perfect for shared dinners and barbecues. Additional seating areas are spread throughout the garden, offering both sun and shade. Inside, the villa combines traditional Tuscan elements such as terracotta floors and wood-beamed ceilings with a cosy and stylish interior. The result is a welcoming atmosphere where guests can unwind and enjoy the beauty of the Chianti countryside. Ground Floor Lounge Three sofas, two armchairs, two coffee tables, sideboard, TV, desk, fireplace, entrance. Kitchen-Diner Fully equipped, table and chairs, dresser, fireplace, frigde. Bedroom 1 Double bed (cannot be converted to twins), wardrobe. Bedroom 2 Twin beds (cannot be converted to double), wardrobe, chair, doors to garden. Bathroom Shower, sink, WC. First Floor Bedroom 3 Double bed (cannot be converted to twins), wardrobe, chest of drawers, chair. En-suite Bathroom Bath with overhead shower, bidet, sink, WC. Bedroom 4 Double bed (cannot be converted to twins), wardrobe, desk and chair. En-suite Bathroom Shower, bidet, sink, WC. Private Pool Length: 12 metres Width: 6 metres Depth: 0.96 - 2.6 metres Entrance: Roman steps Opening times: May to September Fenced: Yes Furnished: Sunloungers, parasols, pagoda with table and chairs Cleansed: Chlorine Distance from villa: 23 metres Local charges Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply. Dog up to 30kg: 8.50 € daily charge per pet Charged based on usage: Heating Villa, Air Conditioning Arrival guide Approach road: Paved Parking: Private, onsite parking

Chianti Classico Home Panoramic View 4

Castellina In Chianti, Toscana, IT
2 Bedrooms 4 Guests
Aug 24 - 27
$150 night

Explore Tuscany and the famous Chianti Classico region from this authentic Tuscan house in the heart of Castellina in Chianti. This beautifully restored old townhouse sleeps 4 people and makes an ideal base for friends or family who want a holiday that combines gastromony, vineyards and the historic cities of Tuscany. The front door is just off the main square, and reached through a peaceful, private garden, with magnificent views over the neighbouring countryside. Elegant stairs lead from the entrance hall up to the first-floor living area. With terracotta floors and antique furniture, the apartment retains its original charm. The spacious living room is furnished with a sofa and armchairs, an open fireplace and a Smart TV. The adjacent kitchen/dining area includes a dining table and a well-equipped kitchen. The kitchen includes a cooker hob, oven, microwave, dishwasher, fridge and coffee machine. Sleeping There are 2 lovely bedrooms, each tastefully decorated with antique furniture including a double bed, wardrobe and chest of drawers. Each bedroom has an en suite bathroom. Bathrooms The 2 en suite bathrooms are all equipped with a shower, basin, bidet and WC. Additional • Free Wifi • Smart TV • Private, fenced garden • Central heating (available 15th October to 15th April) & open fireplace (wood not included) • Fan • Hair dryer • Waste disposal • Washing machine & dryer • Child-friendly • Pets allowed • Public parking (free and paid) outside the village walls, car essential • Check-in from 4.00pm Check out by 10.00am • € 700.00 security deposit by credit card for guests under 21 years of age • Tourist tax paid at the time of booking. Extra costs €350.00 security deposit by credit card is required. Any damages or extraordinary cleaning costs (such as uncollected rubbish, unwashed dishes, etc.) will be deducted from the deposit. Heating = €15 per day from October 15 to April 15, payable at the time of booking; Small pets allowed = €15 per stay, payable at the time of booking Location The house is located in the centre of the village, in the pedestrian area, opposite the Church of San Salvatore and next to the ancient underground walkway of Via delle Volte, which runs along Castellina’s medieval walls. The square has several restaurants and bars where visitors can soak up the atmosphere. The location is ideal for a relaxing holiday with family and friends. It makes an excellent base for gastronomic itineraries through the vineyards of Chianti. For self-catering, the local markets are a treasure trove of the very best local produce, from vegetables to cheese and olive oil. Some of Italy’s most beautiful cities and villages are within easy reach. Florence, is just 45 minutes away and offers some of the finest galleries, museums and architecture in the world. As do the cities of Siena (30 minutes) and Pisa, with its Leaning Tower (1 hour, 30 minutes) and San Gimignano (40 minutes), famous for its many towers. The closest airports are Florence, which is a 45 minute drive, and Pisa, which is 1 hour 25 minutes away.

La Pieve Di San Martino - APT Girasole

Colle Val d'Elsa, Toscana, IT
1 Bedrooms 4 Guests
Aug 30 - Sep 1
$126 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.

Chianti Classico Home Panoramic View 6

Castellina In Chianti, Toscana, IT
3 Bedrooms 6 Guests
Aug 24 - 27
$220 night

A charming Tuscan home in the heart of Castellina in Chianti. This beautifully restored old townhouse sleeps 6 people and makes an ideal base for exploring the glorious Chianti Classico region and the historic cities of Tuscany. The front door is just off the main square, and reached through a peaceful, private garden, with magnificent views over the neighbouring countryside. Elegant stairs lead from the entrance hall up to the first-floor living area. With terracotta floors and antique furniture, the apartment retains its original charm. The spacious living room is furnished with a sofa and armchairs, an open fireplace and a Smart TV. The adjacent kitchen/dining area includes a dining table and a well-equipped kitchen. The kitchen includes a cooker hob, oven, microwave, dishwasher, fridge and coffee machine. Sleeping There are 3 lovely bedrooms, each tastefully decorated with antique furniture including a double bed, wardrobe and chest of drawers. Each bedroom has an en suite bathroom. Bathrooms The 3 en suite bathrooms are all equipped with a shower, basin, bidet and WC. Additional • Free Wifi • Smart TV • Private, fenced garden • Central heating (available from 15th October to 15th April) & open fireplace (wood not included) • Fan • Hair dryer • Washing machine & dryer • Child-friendly • Pets allowed • Public parking (free and paid) outside the village walls • Check-in from 4.00pm, Check out before 10.00am • €700.00 security deposit by credit card for guests under 21 years of age • Tourist tax paid at the time of booking. Extra costs €350.00 security deposit by credit card is required. Any damages or extraordinary cleaning costs (such as uncollected rubbish, unwashed dishes, etc.) will be deducted from the deposit. Heating = €15 per day from October 15 to April 15, payable at the time of booking; Small pets allowed = €15 per stay, payable at the time of booking Location The house is located in the centre of the village, in the pedestrian area, opposite the Church of San Salvatore and next to the ancient underground walkway of Via delle Volte, which runs along Castellina’s medieval walls. The square has several restaurants and bars where visitors can soak up the atmosphere. The location is ideal for a relaxing holiday with family and friends. It makes an excellent base for gastronomic itineraries through the vineyards of Chianti. For self-catering, the local markets are a treasure trove of the very best local produce, from vegetables to cheese and olive oil. Some of Italy’s most beautiful cities and villages are within easy reach. Florence, is just 45 minutes away and offers some of the finest galleries, museums and architecture in the world. As do the cities of Siena (30 minutes) and Pisa, with its Leaning Tower (1 hour, 30 minutes) and San Gimignano (40 minutes), famous for its many towers. The closest airports are Florence, which is a 45 minute drive, and Pisa, which is 1 hour 25 minutes away.

Villa with First Class Amenities, Tuscany Villa 1093

Villa, IT
3 Bedrooms 8 Guests
Oct 17 - 24
$395 night

Property Manager is proud to present Tuscany Villa 1093. "Tuscany Villa 1093", 4-room house 95 m2 on 2 levels. Beautiful and tasteful furnishings: livingsleeping room with 1 double sofabed, open-hearth fireplace, satellite TV, radio, CD-player and DVD. Exit to the terrace. 1 room with 1 french bed (160 cm), showerbidetWC. Exit to the garden. 1 room with 2 beds and showerWC. Exit to the garden. Open kitchen (oven, dishwasher, 5 gas rings, toaster, kettle, microwave, freezer, electric coffee machine) with dining table. Exit to the garden. Upper floor: 1 room with sloping ceilings with 1 french bed (160 cm). ShowerWC. Gas heating, air-conditioning. Comfortable furnishings in the country house style. 2 terraces, porch. Terrace furniture, barbecue, deck chairs, box-room. Beautiful view of the garden, the countryside and the forest. Facilities: washing machine, safe, iron, mosquito net, children's high chair, baby cot. Internet (WiFi, free). Please note: non-smokers only. Maximum 2 small pets dogs allowed.Guided bike and mountain bike tours on request (order, payment on site), mountain bike rental. very beautiful, cosy, rustic single-family house "Villa del Poggio", surrounded by trees and vineyards. 2 km from the centre of Radda in Chianti, 12 km from the centre of Castellina in Chianti, 23 km from the centre of Montevarchi, in the residential district, in the countryside. Private: beautiful, well-kept garden 5'000 m2 (fenced) with lawn and trees, orchard, lawn for sunbathing, swimming pool (12 x 5 m, 02.05.-14.10.). Table tennis, arbour, terrace, garden furniture. Available: bicycles (6). Parking (for 3 cars) on the premises. Grocery 2 km, supermarket 3 km, bus stop 2 km, railway station "Montevarchi" 23 km, outdoor swimming pool 12 km, indoor swimming pool 23 km. Cooking courses bookable on request. Please note: the owner lives on the same property.

Villa Incanto - countryside villa near Siena

Monteroni d'Arbia, Tuscany, IT
9 Bedrooms 18 Guests
Sep 19 - 26
$4,560 night

VILLA INCANTO - SIENA AREA Villa Incanto is a private property immersed in the Tuscan countryside. It is an excellent choice for a relaxing holiday enjoying privacy with the benefit of a private swimming pool and it is also an ideal location for visiting Siena and other cities. Villa Incanto is an independent property comprising of a three-storey main house and an annex. Ground floor: living room with fireplace, pool table, CD reader, sat TV; dining room; kitchen equipped with fireplace, oven, fridge/freezer and dishwasher. There is also a wine cellar in the basement. First floor: living room with fireplace, PC and printer; one double bedroom with en-suite bathroom with bathtub; one double bedroom with en-suite bathroom with shower and Turkish bath; suite with a double bed, office area, dressing room and bathroom with Jacuzzi; two double bedrooms; two double bedrooms with en-suite bathroom with bathtub (the 2 bedrooms share 1 bathroom); bathroom with bathtub. Annex: living area; kitchen; two double bedrooms with en-suite bathrooms with shower. Outside area: private swimming pool (7.5m x 15m); pizza oven; recently refurbished hut with kitchen, BBQ and a bathroom with shower; clay tennis court; five-a-side football field; gym and sauna at 50m from the house; private parking. Facilities: private pool, external kitchen, BBQ, pizza oven, air conditioning (1 unit per bedroom), laundry room, clay tennis court, five-a-side football field, gym and sauna, pool table, bowls area, sat TV, oven, fridge/freezer, dishwasher, wine cellar, private parking, internet WIFI PLEASE NOTE: there is a very competent and helpful housekeeper who lives in a room on the ground floor. Services upon request (extra cost): extra cleaning, catering, table service, driver, and masseur. Sleeps 18 - TU760 Distances Nearest towns: Ville di Corsano 2km, Siena 19km, Monteriggioni 29km. Airports: Pisa 127km, Florence 90km

Villa Incanto - countryside villa near Siena

Monteroni d'Arbia, Tuscany, IT
7 Bedrooms 14 Guests
Sep 19 - 26
$4,023 night

VILLA INCANTO - SIENA AREA Villa Incanto is a private property immersed in the Tuscan countryside. It is an excellent choice for a relaxing holiday enjoying privacy with the benefit of a private swimming pool and it is also an ideal location for visiting Siena and other cities. Villa Incanto is an independent property comprising of a three-storey main house and an annex. Ground floor: living room with fireplace, pool table, CD reader, sat TV; dining room; kitchen equipped with fireplace, oven, fridge/freezer and dishwasher. There is also a wine cellar in the basement. First floor: living room with fireplace, PC and printer; one double bedroom with en-suite bathroom with bathtub; one double bedroom with en-suite bathroom with shower and Turkish bath; suite with a double bed, office area, dressing room and bathroom with Jacuzzi; two double bedrooms; two double bedrooms with en-suite bathroom with bathtub (the 2 bedrooms share 1 bathroom); bathroom with bathtub. Annex (closed off when the villa is booked with under occupancy price for 14 guests): living area; kitchen; two double bedrooms with en-suite bathrooms with shower. Outside area: private swimming pool (7.5m x 15m); pizza oven; recently refurbished hut with kitchen, BBQ and a bathroom with shower; clay tennis court; five-a-side football field; gym and sauna at 50m from the house; private parking. Facilities: private pool, external kitchen, BBQ, pizza oven, air conditioning (1 unit per bedroom), laundry room, clay tennis court, five-a-side football field, gym and sauna, pool table, bowls area, sat TV, oven, fridge/freezer, dishwasher, wine cellar, private parking, internet WIFI PLEASE NOTE: there is a very competent and helpful housekeeper who lives in a room on the ground floor. Services upon request (extra cost): extra cleaning, catering, table service, driver, and masseur. Sleeps 14 - TU760x Distances Nearest towns: Ville di Corsano 2km, Siena 19km, Monteriggioni 29km. Airports: Pisa 127km, Florence 90km

Villa Vigneto

Gaiole in Chianti, IT
4 Bedrooms 8 Guests
Aug 24 - 28
$2,857 night

Featured as the villa in Gino’s Italian Escape, latest ITV Series aired in November 2019. Read more here Villa Vigneto is situated at the very heart of Chianti Classico, about 5 km from Gaiole in Chianti, a medieval village famous for L’Eroica vintage cycling race. The villa sits nestled amongst the vines of an organic winery producing high quality wines and olive oil. This is a traditional Chianti-style villa with a burnt-red tiled roof and magnificent stone walls. Inside the house is beautifully furnished in an authentic Sienese-style with high ceilings, exposed beams and gorgeous terracotta tiles. Air-conditioned throughout the villa accommodates 8 guests with 4 double bedrooms and 4 bathrooms. Measuring approximately 240m2, the villa is surrounded by large terraces (400m2), balconies and 3000m2 of expansive gardens. Spread out over three levels the ground floor houses the living room, sitting area, kitchen, dining area, master bedroom with en-suite, twin bedroom and family bathroom. The sitting area has a large fireplace and is wonderfully cosy in the cooler months. Up on the first floor is another bathroom and a spacious double bedroom with access to a large roof terrace with breath-taking views of the surrounding landscape. The top floor contains a double bedroom and private bathroom complete with 2-person spa bath. Outside is a heated pool and sun loungers where you can sit back and relax, drink in hand, surrounded by lush grapevines. Detox in the sauna, enjoy a spot of tennis. The property also has its own cellar restaurant and plenty of hiking trails to explore. Features: Ground Floor - Kitchen with dishwasher, fridge/freezer, microwave and oven- Living room with 2 sofa-beds- Sitting area with large open fireplace- Dining room with table and chairs for 10 guests- Bedroom with double bed and en-suite bathroom with shower and WC- Twin bedroom and en-suite bathroom with shower and WC First Floor - Bedroom with double bed and direct access to roof terrace- Bathroom with shower and WC- Terrace (120m2) Second Floor - Bedroom with double bed and en-suite bathroom with spa bath and WC Outside Grounds - Heated swimming pool - Covered terrace (300m2)- Outdoor furniture- Barbecue Facilities - Wi-Fi- TV- Reception is open from 8.30 a.m. to 7.30 p.m.- The Winery Restaurant (open Tu-Su) offers buffet breakfast (8.30 a.m. to 10.30 a.m.), light lunches (12.30 p.m. - 4.00 p.m.) and dinner (7.30 p.m. - 9.30 p.m.) (subject to availability) Location: The villa, located in a winery, is a 5-minute drive from Gaiole in Chianti, 30 minutes from Siena and one hour from Florence. Quiet and picturesque, Forbes has previously listed Gaiole as the number one most idyllic place to live in Europe! It indeed is a haven for history buffs and hikers with castles speckling the hills. Gaiole hosts the world famous L’Eroica, a 200 km vintage bike race that takes its participants south travelling through the beautiful countryside of Chianti, Siena, Val d’Arbia, Montalcino, Val d’Orcia and Crete Senesi. The Paolo di Siena, an ancient bareback horse race, has been held in Siena’s civic hub, Piazza del Campo, since 1644. This is a genuinely authentic Sienese experience, and the atmosphere is always electric. As you can probably guess from the name, Chianti is brimming with wineries, many of which are open to visitors. Terms & Conditions: ? Credit card details are required 2 weeks prior to departure for pre-authorisation. 5:00 p.m. to 9.00 p.m. Check-in outside this time may be subject to an extra cost. Please enquire for more details. 8.30 a.m. to 10.30 a.m. Yes. Yes. On request only and with prior agreement with the owner. If accepted, a pet supplement of €30 per pet per week (then €15 for each of the following days) will apply (payable locally). A sofa bed is available on request for 2 additional guests, subject to an extra charge. To be requested at the time of booking, please enquire for further details. A cot is available on request, subject to an extra charge of €20 per day, to be requested at the time of booking, payable locally. Please note that your booking will only be confirmed once we have checked availability with the owner. 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. 3 nights. All other durations on request. Extra cost, payable locally and based on consumption. Available only in low and mid season. Extra €100 per day, 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 adult per night- please enquire if exact amount is required). Wi-Fi connection included. Licence number: CIR: 052013LTN0291 / CIN: IT052013C24O5HRCU6

Nice Country Home in Chianti with a view of Elsa Valley

Castellina in Chianti, IT
4 Bedrooms 8 Guests
Oct 31 - Nov 7
$1,956 night

Villa Di Castellina is an elegant country house in the charming village of Castellina in Chianti in the heart of Chianti Classico. Lined with oaks and holm oaks, the typical vegetation in Chianti, a hidden road on the western slope of the high hills leads down from Castellina to the Villa. From here, there is a magnificent view of the Elsa valley. (Access road asphalted until about 200m before the house). The center of Castellina in Chianti is 4 km away, and other famous villages such as Radda, Gaiole, Panzano, and Greve, and beautiful cities such as Florence and Siena are only a few minutes away by car. The history of Villa La Casina dates back to the 10th century. After restoration and modernization, even the beautiful driveway puts you in a special mood, where flowers, lavender, and rosemary fill the entrance area. Interiors are spacious and comfortably furnished. The elegant furnishings create an exclusive ambiance. Just as impressive as the interiors are the outdoor areas with breathtaking views of the ancient, traditional terraces of the Antico Podere vineyard. The Villa has been finely restored and provides A / C in the rooms, TV, Wifi, oven, double fridge / freezer, dishwasher, a good selection of pots, plates, dishes and glasses for 12 people. Toaster, kettle, coffee machine, microwave. Outside, a splendid private swimming pool is available for guests. The price also includes an intermediate cleaning of four hours / week, WiFi internet and a first supply of kitchen products. Service on request - Private chef service/cooking lessons - Daily villa cleaning - Car with driver - Bicycle rental - Private guided tours - Personal trainer - Yoga instructor

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