
Villa vacation rentals in Gaiole in Chianti
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Top-rated villa rentals in Gaiole in Chianti
Guests agree: these villas are highly rated for location, cleanliness, and more.

The Farmhouse Cottage
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

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.

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

Tuscany Country House Villa Claudia
La Nostra Country House è incastonata in un bellissimo Casale antico, finemente ristrutturato, panoramicissimo, costruito a margine dell'antico Borgo di Canneto, insediamento rurale nel territorio di San Miniato, risalente al 785 d.c. Il Casale, immerso nella Natura ma dotato di ogni comfort moderno, vi regalerà momenti indimenticabili, potendo scegliere tra vacanze in assoluto Relax, attività culturali (vicinissime le città d'Arte della Toscana), gustosi tour enogastronomici e tanto altro!

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

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

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.

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Villa Poggio in Mandria in Chianti
Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.
Popular amenities for Gaiole in Chianti villa rentals
Private villa rentals

Charming villa 15' walk to center stunning view

Ancient tower w/ private pool Vacavilla Exclusive

Terra Antica Suites & Villas – Cervognano

The Lazy Oak

[Le rondini in Tuscany] Exclusive View Pool Villa

The Tancherina, a Tuscan heart

Beautiful Country House, near Siena with jacuzzi

[Cortona] Historic Villa with Pool and Park
Luxury villa rentals

Casale La Querce-Tuscan Farmhouse with pool & view

Valluccia 51

Romantic Villa with private pool and fabulous view

La Vignaccia (Farmhouse) - villa w/private pool

Villa "The memory of time"

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villetta dei Fagiani - pools, Jacuzzi in Florence

Dream House in Tuscany, with Amazing View and Pool
Villa rentals with a pool

Lovely Villa situated in nature

La Pieve – Tuscan Hideaway in Chianti

Il Castellaccio Villa

La Cipresseta Estate | Cipresso House

Exclusive Farmhouse Pool & View of San Gimignano

Romantic Villa with private pool - "Il Pollaio"

Beautiful tuscan country house

Pompana Rustic Charm Casale
Quick stats about villa rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti vacation rentals start at G$37,655 GYD per night before taxes and fees

Verified guest reviews
Over 40 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, 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!
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazzale Michelangelo
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Mugello Circuit
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Medici Chapels
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Basilica di Santa Croce
- Palazzo Vecchio
- Castiglion del Bosco Winery
- Teatro Verdi