
Villa holiday rentals in Gaiole in Chianti
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Quick stats about villa rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti holiday rentals start at $337 AUD per night before taxes and fees

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Over 50 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Gaiole in Chianti rentals

4.9 Average rating
Gaiole in Chianti stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated villa rentals in Gaiole in Chianti
Guests agree: These villas are highly rated for location, cleanliness and more.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
ValueFamilyTV
4.93 out of 5 average rating, 256 reviews
Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
LocationFamilyBreakfast
4.9 out of 5 average rating, 241 reviews
Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.
ValueLocationBathroom
4.99 out of 5 average rating, 131 reviews
Sestuccia
Villa Sestuccia is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. In this wonderful villa there are 4 bedrooms with private bathrooms.The exterior of the villa is composed by 4 living areas: the "wisteria living", the "panorama living", the "Mondrian living", the "outdoor patio" and a vegetable garden. There is also a swimming pool, a SPA and an outdoor hot tub for 6 people. Inside the fenced property you can find a chicken coop and a beautiful vineyard. Enjoy!
LocationFamilyBathroom
4.99 out of 5 average rating, 75 reviews
Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
LocationFamilyHot tub
4.93 out of 5 average rating, 335 reviews
Riecine Capanna 4
Riecine Capanna 4 is a luxurious holiday home set on the renowned Riecine wine estate, ideal for two couples or a small family. This elegant stone house is surrounded by the typical Chianti landscape of rolling hills, vineyards and woodlands. The large pool, the beautifully maintained garden and the high-quality interior make this a truly special retreat. Guests can also look forward to a complimentary tour of the Riecine estate, including a private wine tasting.
FamilyLocationOutdoor spaces
5.0 out of 5 average rating, 9 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
ValueFamilyAccuracy
4.96 out of 5 average rating, 102 reviews
Villa La Doccia, Greve in Chianti
Villa La Doccia is located approximately 8 minutes by car from the centre of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet, peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscape. The location is perfect for those who want to relax in the countryside while still being close to the centre of Greve in Chianti.
FamilyLocationCheck-in
4.85 out of 5 average rating, 180 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
FamilyValueLong stay
4.98 out of 5 average rating, 107 reviews
Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.
LocationFamilyBathroom
4.98 out of 5 average rating, 120 reviews
The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.
FamilyLocationCheckout
5.0 out of 5 average rating, 190 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
LocationValueHospitality
4.89 out of 5 average rating, 309 reviewsPopular amenities for Gaiole in Chianti villa rentals
Private villa rentals

Podere il Trebbio
LocationValueGetting around
4.92 out of 5 average rating, 88 reviews
Casa Faraona, villa with private pool
FamilyLocationCleanliness
5.0 out of 5 average rating, 32 reviews
Montemarcoli
LocationFamilyNearby
5.0 out of 5 average rating, 34 reviews
Villa Montemaggio
LocationValueNearby
4.86 out of 5 average rating, 35 reviews
Ancient tower w/ private pool Vacavilla Exclusive
LocationValueLayout
4.83 out of 5 average rating, 30 reviews
Villa with pool in Chianti - Castellare Petroso
FamilyLocationComfort
5.0 out of 5 average rating, 33 reviews
Villa il Balocco
LocationFamilyPool
4.98 out of 5 average rating, 43 reviews
Lucignano Secondo – La Villa
FamilyLocationBathroom
4.89 out of 5 average rating, 35 reviewsLuxury villa rentals

Wine Experience Villa in Montepulciano
FamilyValueBreakfast
4.97 out of 5 average rating, 126 reviews
Villa of the 2 Olive Trees (Abbadia Isola)
ValueLocationLaundry
4.97 out of 5 average rating, 174 reviews
Podere Scaluccia Chianti Farmhouse, Florence
ValueFamilySleep quality
4.99 out of 5 average rating, 123 reviews
Villa with pool in Chianti Area
ValueFamilyComfort
4.95 out of 5 average rating, 73 reviews
Villa marielena chianti farmhouse with hot tub - v
LocationFamilyBathroom
5.0 out of 5 average rating, 10 reviews
Villa Holm stunning view 10 mn walk to city centre
FamilyLocationCondition
5.0 out of 5 average rating, 56 reviews
Casa Gioia Vallucino
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 13 reviews
Chianti Tuscany: villa with a view
FamilyLocationBiking
4.93 out of 5 average rating, 81 reviewsVilla rentals with a pool

Villa L'Olivo w/Private pool (Close San Gimignano)
FamilyLocationCondition
4.99 out of 5 average rating, 101 reviews
[Le rondini in Tuscany] Exclusive View Pool Villa
LocationFamilyCleanliness
4.92 out of 5 average rating, 25 reviews
The Villa of the Spendthrift Brigade!
FamilyLocationAmenities
5.0 out of 5 average rating, 28 reviews
La Cipresseta Estate | Cipresso House
LocationFamilyCheckout
4.98 out of 5 average rating, 41 reviews
Villa Fonte Caresino 1
LocationValueNearby
4.74 out of 5 average rating, 77 reviews
Villa Montanina - exclusive relaxation in Tuscany
ValueFamilyGetting around
4.99 out of 5 average rating, 85 reviews
Coaching House
FamilyLocationKitchen
5.0 out of 5 average rating, 67 reviews
STUNNING 5BR VILLA WITH POOL IN CHIANTI TUSCANY
FamilyValueTV
4.81 out of 5 average rating, 36 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce





