Compare Gaiole in Chianti Villa Deals

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Featured Villas in Gaiole in Chianti

Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montisi Tuscany
At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

VIA DI SINALUNGA 65 Foiano della Chiana AR
$75 nightly
The price is $87 total per night
$87 total
Oct 31 - Nov 1
Total with taxes and fees
Guests staying at Artisti del Cavallo Tourism enjoy free WiFi in public areas, a terrace, and a garden. There's free parking and an airport shuttle for a fee. Staff members can answer questions about accommodations, and also provide a safe deposit box at the front desk. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include barbecue grills, a picnic area, and a banquet hall.
Pet friendly
Parking included
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Impruneta (Florence) Tuscany
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly villa include a garden and barbecue grills.
Pool
Hot Tub
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

San Gimignano SI, Italy
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Additional amenities include a garden and barbecue grills.
Pool
Kitchen
Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Toscana Città Metropolitana di Firenze
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Relais Badia a Passignano

Relais Badia a Passignano

Via Martiri di Pratale 12 Barberino Tavarnelle FI
Guests of this villa have access to a seasonal outdoor pool and a garden.
Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool

impruneta Toscana
Free Cancellation
$1,075 nightly
The price is $1,080 total per night
$1,080 total
Nov 1 - Nov 2
Total with taxes and fees
Guests of this villa enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. Transportation is made easy with limo/town car service. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this golf villa include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Kitchen
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

San Casciano in Val di Pesa Tuscany
Guests of this villa enjoy features like an outdoor pool, a gym, and a terrace. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Kitchen
Gorgeous view on vineyards, Stone Tuscan private Villa

Gorgeous view on vineyards, Stone Tuscan private Villa

Toscana Provincia di Siena
Guests staying at this villa enjoy a hot tub, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Gaiole in Chianti

    Castello di Spaltenna- Small Luxury Hotels of the World

    Castello di Spaltenna- Small Luxury Hotels of the World

    Via Spaltenna 13 Gaiole in Chianti SI
    $330 nightly
    The price is $374 total per night from Oct 30 to Oct 31
    $374 total
    Oct 30 - Oct 31
    Total with taxes and fees
    9.6/10 Exceptional! (295 reviews)
    Castello di Tornano Wine Resort

    Castello di Tornano Wine Resort

    Loc. Tornano Gaiole in Chianti SI
    $152 nightly
    The price is $176 total per night from Oct 26 to Oct 27
    $176 total
    Oct 26 - Oct 27
    Total with taxes and fees
    Radisson Blu Hotel, Florence

    Radisson Blu Hotel, Florence

    Via Giovanni Agnelli 33 Florence FI
    $99 nightly
    The price is $124 total per night from Nov 15 to Nov 16
    $124 total
    Nov 15 - Nov 16
    Total with taxes and fees

Luxury Villas

Book luxury villas in Gaiole in Chianti
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Gaiole in Chianti. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Gaiole in Chianti, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Gaiole in Chianti
You won’t have a problem finding your own space in Gaiole in Chianti. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Gaiole in Chianti on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Gaiole in Chianti rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Gaiole in Chianti Villas essential information

Accommodation
1767 Villas
Lowest Price
$87
Highest Price
$1,080
Popular accommodation
Montalcino: Private villa in the heart of Tuscany, private pool, A/C, Artisti del Cavallo Tourism, Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City, Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano, Villa Bartolini Baldelli - Authentic XV century villa with garden and pool, Relais Badia a Passignano, Exclusive Estate | Personal Concierge & Heated Pool, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C, Gorgeous view on vineyards, Stone Tuscan private Villa