Gaiole in Chianti Vacation Rentals

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Dec 31 - Jan 1
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Jan 1 - Jan 2
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Jan 2 - Jan 4
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Jan 9 - Jan 11

Our top choices for Gaiole in Chianti vacation rentals

Front of property
L' Eroico

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
Outdoor pool, sun loungers
Rocca di Castagnoli

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is ￥26,705
￥30,845 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rocca di Castagnoli
Dining
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Gaiole in chianti
The price is ￥42,542
￥43,276 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Pool
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is ￥84,637
￥101,045 total
includes taxes & fees
Jan 13 - Jan 14, 2026
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
TV, fireplace
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (8)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is ￥190,854
￥195,260 total
includes taxes & fees
Jan 9 - Jan 10, 2026
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Pool
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is ￥1,092,433
￥1,184,234 total
includes taxes & fees
Jan 1 - Jan 2, 2026
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Dining
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
The price is ￥50,380
￥51,114 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Dining
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
The price is ￥64,518
￥65,253 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Chalet | In-room safe, cribs/infant beds, bed sheets
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1614)
"It was a grt place to stay"
United States
Sunitha
The price is ￥7,774
￥9,836 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hu Firenze Camping In Town
Quadruple Room, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is ￥11,857
￥15,394 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Al Mercato B&B
Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ￥18,492
￥20,341 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Cassia di Baccano
Birthday party area
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (423)
"A great location!"
Canada
Cheryl
The price is ￥21,902
￥24,826 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siena Vip
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is ￥14,771
￥21,757 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Palazzo al Torrione 2
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (194)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Balcony
Cameracaffè Centro

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is ￥13,815
￥16,298 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cameracaffè Centro
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ￥29,758
￥33,469 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PALAZZO DEL PAPA
Exterior
Sportland

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Exterior detail
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ￥21,765
￥24,675 total
includes taxes & fees
Jan 31 - Feb 1, 2026
Villa il Fedino
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | View from room
B&B Palazzo del Magnifico

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
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.
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Top Gaiole in Chianti Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Staff"
Young 3-night trip
Posted 2 days ago
Hotel Athena

Find out more about Gaiole in Chianti

Search for holiday rentals in Gaiole in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in Gaiole in Chianti using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Gaiole in Chianti?

Yes, we have vacation rentals close to the most popular attractions in Gaiole in Chianti, or you can choose a more secluded option if you're looking for relaxation. The spas and wineries are several reasons why visitors like Gaiole in Chianti. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Gaiole in Chianti has to offer?

Borgo Argiano: Visitors like this Gaiole in Chianti vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 34 Expedia vacation rentals, you're sure to find just the right place for your Gaiole in Chianti stay.

What’s there to see and do in Gaiole in Chianti?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

What’s a vacation rental in Gaiole in Chianti like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Gaiole in Chianti. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.