A stone castle with battlements overlooking a lush valley with vineyards.

Gaiole in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Gaiole in Chianti vacation homes

A dining area with a table and chairs, a sofa, and large windows with curtains.

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

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is CA $1,486
CA $1,629 total
includes taxes & fees
Oct 12 - Oct 13
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
A swimming pool with a colorful inflatable ring and a water fountain.

2. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."
Germany
Johanna K.
The price is CA $650
CA $803 total
includes taxes & fees
Oct 6 - Oct 7
Farmhouse in Chianti
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

3. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (25 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is CA $130
CA $255 total
includes taxes & fees
Oct 6 - Oct 7
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

4. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is CA $109
CA $196 total
includes taxes & fees
Oct 11 - Oct 12
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

5. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $158
CA $277 total
includes taxes & fees
Oct 8 - Oct 9
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

6. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is CA $115
CA $157 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful corner with garden between Chianti and Crete, very close to Old Town
A view through a wooden door of a courtyard with stone walls and potted plants.

7. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is CA $200
CA $290 total
includes taxes & fees
Oct 9 - Oct 10
Chianti Craft House Badia a Passignano
A brick building with a garden, a metal fence, and a clear sky.

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $346
CA $433 total
includes taxes & fees
Oct 11 - Oct 12
Casa Marisa in Castellina in Chianti
A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

9. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is CA $417
CA $577 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

10. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is CA $520
CA $589 total
includes taxes & fees
Oct 10 - Oct 11
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
A stone building with a gravel path, outdoor seating, and greenery.

11. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $375
CA $438 total
includes taxes & fees
Oct 6 - Oct 7
The Arch Among the Hills of Castellina
A clear blue pool with a view of green hills and a distant building.

12. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

13. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (4 reviews)
"Pros: Guido og Angela var helt fantastiske værter og deres medhjælper sørgede godt for os med friske grøntsager fra haven. Poolen var perfekt og altid ren og pæn. For os var det helt perfekt vi kun var to familier og at der var ro Cons: Vi har ingen kritik punkter ☺️"
Denmark
Anonymous traveller
The price is CA $567
CA $636 total
includes taxes & fees
Oct 7 - Oct 8
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

14. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveller
The price is CA $498
CA $585 total
includes taxes & fees
Oct 13 - Oct 14
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

15. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is CA $549
CA $618 total
includes taxes & fees
Oct 6 - Oct 7
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

16. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
Monteroni d'Arbia
The price is CA $152
CA $189 total
includes taxes & fees
Oct 24 - Oct 25
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
A large estate with a main building surrounded by lush greenery and vineyards.

17. Holiday Home with Vineyard Vibes

Holiday Home with Vineyard Vibes
San Casciano in Val di Pesa
9.4 out of 10, Exceptional, (30 reviews)
"I stayed here because I wanted a clean and comfortable place close to Florence for one night. The room and bathroom were tidy and provided exactly what I needed for a restful stopover."
United States
Anonymous traveller
Holiday Home with Vineyard Vibes
A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

18. Little cozy house

Little cozy house
Loro Ciuffenna
The price is CA $112
CA $141 total
includes taxes & fees
Oct 13 - Oct 14
Little cozy house
A rustic building with a brick facade, a small arched window, and a door.

19. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."
United States
Shanti R.
The price is CA $241
CA $295 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Tuscan-style apartment Suitable for families. Pets allowed
A stone building with a rustic staircase and a view of the sea.

20. Podere I Rovai-apt IL RIFUGIO-amazing view Tuscany

Podere I Rovai-apt IL RIFUGIO-amazing view Tuscany
Reggello ( Firenze )
The price is CA $128
CA $210 total
includes taxes & fees
Nov 1 - Nov 2
Podere I Rovai-apt IL RIFUGIO-amazing view Tuscany
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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Amazing hotel, amenities, food, staff & location. This was a gem to find & so enjoyable to stay at. Loved it"
Banafsheh 3-night trip
Posted 3 hours ago
Radisson Blu Hotel, Florence

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews
82
Accommodation
1602 Vacation Homes
Lowest Price
CA $141
Highest Price
CA $1,629