Compare Gaiole in Chianti Villa Deals

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Featured Villas in Gaiole in Chianti

Villa with Concierge service and heated pool

Villa with Concierge service and heated pool

impruneta Toscana
$1,720 nightly
The price is $1,725 total per night
$1,725 total
Aug 17 - Aug 18
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
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

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
"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 a garden.
Pool
Kitchen
Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena

Fonterutoli Provincia di Siena
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This villa also has a garden.
Pool
Hot Tub
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 in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino, exclusive for you, stunning view!!!

Montalcino Provincia di Siena
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Hot Tub
Luxury villa just 14 km from Florence. Sleeps 16 with sauna & gym!

Luxury villa just 14 km from Florence. Sleeps 16 with sauna & gym!

Firenze Toscana
Guests of this villa enjoy features like a gym, a sauna, and laundry facilities. Other amenities at this family-friendly villa include barbecue grills and a garden.
Pool
Kitchen
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Monteriggioni SIENA Toscana
At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. Transportation is made easy with limo/town car service. This family-friendly villa also has barbecue grills.
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
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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
    $391 nightly
    The price is $441 total per night from Aug 9 to Aug 10
    $441 total
    Aug 9 - Aug 10
    Total with taxes and fees
    9.6/10 Exceptional! (278 reviews)
    Castello di Tornano Wine Resort

    Castello di Tornano Wine Resort

    Loc. Tornano Gaiole in Chianti SI
    $220 nightly
    The price is $251 total per night from Aug 6 to Aug 7
    $251 total
    Aug 6 - Aug 7
    Total with taxes and fees
    9/10 Wonderful! (116 reviews)
    Ultimo Mulino Wellness Country Hotel

    Ultimo Mulino Wellness Country Hotel

    Localita La Ripresa di Vistareni Gaiole in Chianti SI
    $164 nightly
    The price is $189 total per night from Aug 24 to Aug 25
    $189 total
    Aug 24 - Aug 25
    Total with taxes and fees
    8.8/10 Excellent! (160 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
1879 Villas
Lowest Price
$189
Highest Price
$1,725
Popular accommodation
Villa with Concierge service and heated pool, Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C, Private villa in the heart of chianti with view of siena, Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City, Villa in Montalcino, exclusive for you, stunning view!!!, Luxury villa just 14 km from Florence. Sleeps 16 with sauna & gym!, Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence. , Villa Bartolini Baldelli - Authentic XV century villa with garden and pool