Compare Gaiole in Chianti Villa Deals

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Featured Villas in Gaiole in Chianti

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.
Pool
Kitchen
Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Greve in Chianti (Firenze) Toscana
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Transportation is made easy with limo/town car service. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include local meal delivery service, a garden, and barbecue grills.
Pool
Hot Tub
CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

Strada In Chianti Città Metropolitana di Firenze
Guests of this villa have access to an outdoor pool, a gym, and a hot tub. Transportation is made easy with limo/town car service. Additional amenities include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
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
La Ruota - Village house rental in Duddova, Chianti

La Ruota - Village house rental in Duddova, Chianti

Duddova Tuscany
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

Civitella di val di chiana Province of Arezzo
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills. This family-friendly villa also has a living plant wall.
Pool
Kitchen
Marvelous home just steps from the Chianti and beyond

Marvelous home just steps from the Chianti and beyond

cavriglia Tuscany
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Wonderful private villa for 4 guests with pool, A/C, WIFI, TV and terrace

Wonderful private villa for 4 guests with pool, A/C, WIFI, TV and terrace

Asciano Tuscany
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
"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
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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
    $418 nightly
    The price is $471 total per night from Oct 5 to Oct 6
    $471 total
    Oct 5 - Oct 6
    Total with taxes and fees
    9.6/10 Exceptional! (286 reviews)
    Castello di Tornano Wine Resort

    Castello di Tornano Wine Resort

    Loc. Tornano Gaiole in Chianti SI
    $210 nightly
    The price is $241 total per night from Oct 11 to Oct 12
    $241 total
    Oct 11 - Oct 12
    Total with taxes and fees
    9.2/10 Wonderful! (124 reviews)
    Radisson Blu Hotel, Florence

    Radisson Blu Hotel, Florence

    Via Giovanni Agnelli 33 Florence FI
    $164 nightly
    The price is $196 total per night from Oct 11 to Oct 12
    $196 total
    Oct 11 - Oct 12
    Total with taxes and fees
    8.8/10 Excellent! (161 reviews)

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
1841 Villas
Lowest Price
$196
Highest Price
$471
Popular accommodation
Relais Badia a Passignano, Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti, CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5, Villa Bartolini Baldelli - Authentic XV century villa with garden and pool, La Ruota - Village house rental in Duddova, Chianti, Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment, Marvelous home just steps from the Chianti and beyond, Wonderful private villa for 4 guests with pool, A/C, WIFI, TV and terrace, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C