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

Holiday Homes in Gaiole in Chianti

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Gaiole in Chianti holiday homes

Interior

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 €1,398
includes taxes & fees
2 Aug - 3 Aug
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Exterior detail

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.4 out of 10, Exceptional, (23 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 €165
includes taxes & fees
3 Aug - 4 Aug
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Outdoor dining

3. 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 €260
includes taxes & fees
24 Aug - 25 Aug
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Dining

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

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is €289
includes taxes & fees
2 Aug - 3 Aug
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Pool

5. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi
Rosennano
The price is €548
includes taxes & fees
1 Aug - 2 Aug
Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi
Spa

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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is €183
includes taxes & fees
5 Aug - 6 Aug
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Pool

7. 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 €334
includes taxes & fees
1 Aug - 2 Aug
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
TV

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is €286
includes taxes & fees
2 Aug - 3 Aug
Casa Marisa in Castellina in Chianti
Outdoor dining

9. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is €544
includes taxes & fees
30 Aug - 31 Aug
The Arch Among the Hills of Castellina
Outdoor dining

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 €120
includes taxes & fees
3 Aug - 4 Aug
Peaceful corner with garden between Chianti and Crete, very close to Old Town
Interior

11. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is €191
includes taxes & fees
29 Aug - 30 Aug
Chianti Craft House Badia a Passignano
Interior

12. Little cozy house

Little cozy house
Loro Ciuffenna
The price is €84
includes taxes & fees
3 Aug - 4 Aug
Little cozy house
Pool

13. 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 €455
includes taxes & fees
27 Aug - 28 Aug
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Property grounds

14. 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 €703
includes taxes & fees
9 Aug - 10 Aug
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Outdoor dining

15. 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, (2 reviews)
"Pros: Wunderschönes charmantes, rustikales Ferienhaus in der wunderschönen Toskana. Tolle Lage, sehr freundlicher und charmanter Gastgeber. Senore Guidi und seine Ehefrau sind zauberhafte Gastgeber. Sehr hilfsbereit und zuvorkommend! Die Fotos der Unterkunft stimmen zu 100% überein! Toller Poolbereich. Senor Guidi hat zur Wein- und Olivenöl -Verkostung eingeladen und uns auf Anfrage zu einer persönlichen Begehung seiner Oliven-und-Weinberge mitgenommen. Sehr persönliche und menschliche...
Germany
Anonymous traveller
The price is €483
includes taxes & fees
8 Aug - 9 Aug
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Outdoor dining

16. House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is €264
includes taxes & fees
29 Aug - 30 Aug
House with views of the Chianti
Property grounds

17. 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, (1 review)
"Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "
France
YVES A.
The price is €191
includes taxes & fees
1 Aug - 2 Aug
Cozy Tuscan-style apartment Suitable for families. Pets allowed
Living area

18. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Greve in Chianti
10.0 out of 10, Exceptional, (10 reviews)
"This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!"
United States
Linda L.
The price is €350
includes taxes & fees
15 Aug - 16 Aug
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Outdoor pool

19. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is €127
includes taxes & fees
2 Aug - 3 Aug
Casa Vacanze Le Case
Exterior detail

20. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (9 reviews)
"Loved it!"
United States
Ryan C.
The price is €184
includes taxes & fees
29 Aug - 30 Aug
Exclusive Stone Tower.
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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Really nice hotel! The gardens at the back of the property were a really nice surprise!"
Jerome 1-night trip
Posted 7 hours ago
La Certosa di Pontignano

Find out more about Gaiole in Chianti

Gaiole in Chianti Holiday Homes information

Number of reviews
42
Accommodation
1493 Holiday Homes
Lowest Price
€84
Highest Price
€1,398