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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Gaiole in Chianti vacation homes

A swimming pool with a colorful inflatable ring and a water fountain.

1. 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 $648
CA $802 total
includes taxes & fees
Oct 10 - Oct 11
Farmhouse in Chianti
A dining area with a table and chairs, a sofa, and large windows with curtains.

2. '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 $1,606
CA $1,749 total
includes taxes & fees
Oct 11 - Oct 12
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
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 $129
CA $256 total
includes taxes & fees
Oct 7 - Oct 8
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $158
CA $278 total
includes taxes & fees
Oct 7 - Oct 8
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

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

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is CA $416
CA $576 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
A bedroom with a bed, a chair, a nightstand, a lamp, a decorative headboard, and a window with curtains.

6. 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
Nov 1 - Nov 2
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
An outdoor patio with a wooden pergola, a sofa, a table, and chairs.

7. Blue villa surrounded by greenery between Arezzo Florence and Siena

Blue villa surrounded by greenery between Arezzo Florence and Siena
TERRANUOVA BRACCIOLINI
Blue villa surrounded by greenery between Arezzo Florence and Siena
A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

8. 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 $565
CA $634 total
includes taxes & fees
Oct 5 - Oct 6
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
A view through a wooden door of a courtyard with stone walls and potted plants.

9. 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 $291 total
includes taxes & fees
Oct 5 - Oct 6
Chianti Craft House Badia a Passignano
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

10. 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 modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

11. Little cozy house

Little cozy house
Loro Ciuffenna
The price is CA $112
CA $141 total
includes taxes & fees
Oct 8 - Oct 9
Little cozy house
A brick building with a garden, a metal fence, and a clear sky.

12. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $345
CA $432 total
includes taxes & fees
Oct 11 - Oct 12
Casa Marisa in Castellina in Chianti
A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

13. 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 $524
CA $610 total
includes taxes & fees
Oct 7 - Oct 8
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
A clear blue pool with a view of green hills and a distant building.

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

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
The price is CA $811
CA $817 total
includes taxes & fees
Oct 5 - Oct 6
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
A stone building with a gravel path, outdoor seating, and greenery.

15. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $374
CA $437 total
includes taxes & fees
Oct 5 - Oct 6
The Arch Among the Hills of Castellina
A stone building with a sign reading "VIA DI CALZOLERIA".

16. THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart of the main street
Siena City Centre
8.4 out of 10, Very good, (5 reviews)
"I stayed for a month and found the apartment ti be very comfortable and si convenient for all that Siena has to offer."
United States
Louise B.
The price is CA $161
CA $264 total
includes taxes & fees
Oct 5 - Oct 6
THE TOLOMEI - apartment in the heart of the main street
A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

17. 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 $547
CA $616 total
includes taxes & fees
Oct 5 - Oct 6
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
A garden with various plants and flowers, a pathway, and a swing set.

18. Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is CA $224
CA $277 total
includes taxes & fees
Oct 3 - Oct 4
Apartment House with garden Tuscany Chianti , Florence 15km.
A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

19. 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 $86
CA $173 total
includes taxes & fees
Oct 7 - Oct 8
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

20. 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 $576
CA $645 total
includes taxes & fees
Oct 10 - Oct 11
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"The property was very clean and there was so much to do without even leaving it. We stayed there for a few nights only"
Kseniia 3-night trip
Posted 14 hours ago
Hu Firenze Camping In Town

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews
130
Accommodation
1602 Vacation Homes
Lowest Price
CA $141
Highest Price
CA $1,749