
Villa vacation 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 vacation rentals start at G$50,104 GYD per night before taxes and fees

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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!
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
FamilyValueHeating

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
FamilyLocationLong stay

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
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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.
FamilyLocationWifi

Villa La Doccia, Greve in Chianti
Villa La Doccia is located about an 8-minute drive from the center of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet and peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscapes. The location is ideal for those who want to relax in the countryside but at the same time be close to the center of Greve in Chianti.
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Il Vichiaccio: Florence Villa with Jacuzzi
Cozy Chianti Villa close to Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!
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Sestuccina
Sestuccia Cantina is romantic cottage with two double bedrooms and sofa bed in the living room. The villa is located a few kilometers from Gaiole in Chianti and is surrounded by vineyards, with incredible views of Orchard Castle, The villa is completely built in stone with a beautiful shaded terrace. Guests have access to a relaxing bar area with heated Jacuzzi for 6 persons. Inside the park there is a Chicken Coop with fresh eggs every morning and organic garden.
FamilyLocationHospitality

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.
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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.
LocationFamilyHospitality

Casanova di Bricciano
Set on the grounds of a family-run organic winery, this stone-built villa offers a harmonious blend of Tuscan charm and modern comfort. Positioned above a tiny hamlet in the rolling Chianti hills, it enjoys panoramic views over vineyards, olive groves and forested slopes. With a spacious interior and generous outdoor areas, the villa is ideal for a memorable stay with family or friends.
FamilyLocationNearby

"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).
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Agriturismo Podere Scaluccia Chianti, Florence
The farmhouse is located 15 minutes (8 km) from the center of Florence, a city rich in art and culture, and is surrounded by beautiful panoramic views of the hills, at the entrance to Chianti. The house is old: traditional materials such as stone, wood and terracotta are the main features. The outdoor garden is available to everyone! To learn more, search for Podere Scaluccia
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Popular amenities for Gaiole in Chianti villa rentals
Private villa rentals

The Tower
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Casa Faraona, villa with private pool
LocationFamilyKitchen

Montemarcoli
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Villa il Balocco
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Villa with pool in Chianti - Castellare Petroso
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Ancient tower w/ private pool Vacavilla Exclusive
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Lucignano Secondo – La Villa
LocationFamilyKitchen

La Fornace di Tremoleto – Villa with Private Pool
FamilyLocationAir conditioning
Luxury villa rentals

Luxury Villa in the very heart of Chianti
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Villa dei 2 Ulivi (Abbadia Isola)
ValueFamilyHeating

Wine Experience Villa in Montepulciano
ValueLocationHeating

Tuscany View - Villa Arianna
FamilyValueCheck-in

L'Apparita del Peruzzi | Villa | Private Pool & AC
LocationFamilyComfort

Villa marielena chianti farmhouse with hot tub - v
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romignano wine farm
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Chianti Tuscany: villa with a view
LocationFamilyComfort
Villa rentals with a pool

Farmhouse in Chianti
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[Le rondini in Tuscany] Exclusive View Pool Villa
LocationFamilyView

Coaching House
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Villa in Tuscany with panoramic private pool
LocationFamilyHospitality

The Lazy Oak
LocationFamilyGrill

Villa Fontecaresino 1
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Villa La Poggerina, private pool and amazing view
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Exclusive Tuscan Villa with private pool
LocationFamilyQuiet
Destinations 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
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Basilica of Santa Croce
- Medici Chapel





