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

Gaiole in Chianti Holiday Rentals

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Our top choices for Gaiole in Chianti holiday rentals

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is NZ$271
includes taxes & fees
12 Nov - 13 Nov
L' Eroico

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 NZ$1,702
includes taxes & fees
10 Nov - 11 Nov
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

3. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is NZ$3,124
includes taxes & fees
15 Nov - 16 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

4. 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 NZ$956
includes taxes & fees
10 Nov - 11 Nov
Farmhouse in Chianti

5. 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 NZ$587
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

6. 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 NZ$626
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

7. 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 NZ$832
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

8. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is NZ$261
includes taxes & fees
10 Nov - 11 Nov
Agriturismo La Ferrozzola

9. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is NZ$239
includes taxes & fees
11 Nov - 12 Nov
Casa Vacanze Squarcialupi

10. 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, (28 reviews)
"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...
United States
Michael F.
The price is NZ$305
includes taxes & fees
10 Nov - 11 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

11. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is NZ$521
includes taxes & fees
13 Nov - 14 Nov
Terre di Baccio

12. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (276 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is NZ$184
includes taxes & fees
26 Nov - 27 Nov
Relais Villa Olmo - Place of Charme

13. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is NZ$137
includes taxes & fees
10 Nov - 11 Nov
Chianti Village Morrocco

14. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (34 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$149
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel

15. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NZ$189
includes taxes & fees
10 Nov - 11 Nov
Villa Cassia di Baccano

16. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is NZ$316
includes taxes & fees
12 Nov - 13 Nov
Relais Villa Belpoggio - Residenza d'Epoca

17. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (61 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is NZ$201
includes taxes & fees
12 Nov - 13 Nov
Guild Living Siena Senior Resort & Residence

18. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is NZ$219
includes taxes & fees
1 Dec - 2 Dec
Antica Pieve B&B

19. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is NZ$324
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino

20. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,805 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is NZ$115
includes taxes & fees
10 Dec - 11 Dec
Hu Firenze Camping In Town
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

Find out more about Gaiole in Chianti

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gaiole in Chianti holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gaiole in Chianti. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gaiole in Chianti. Seeing all the best attractions is bound to make you fall in love with Gaiole in Chianti. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gaiole in Chianti short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Gaiole in Chianti?

Yes, there are holiday rentals close to the most popular sights in Gaiole in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Gaiole in Chianti has to offer?

Borgo Argiano: This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 18 Expedia holiday rentals, you're guaranteed 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 Terme Antica Querciolaia. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gaiole in Chianti. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.