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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Gaiole in Chianti vacation rentals

Exterior

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 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 AED 519
AED 605 total
includes taxes & fees
6 Aug - 7 Aug
L' Eroico
Exterior

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is AED 1,006
AED 1,141 total
includes taxes & fees
17 Aug - 18 Aug
Borgo Argenina
Interior

3. Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi

Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi
Gaiole in Chianti
The price is AED 3,254
AED 3,633 total
includes taxes & fees
9 Aug - 10 Aug
Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi
Outdoor pool

4. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...
United States
Lara W.
The price is AED 1,906
AED 2,330 total
includes taxes & fees
1 Sep - 2 Sep
Farmhouse in Chianti
Outdoor dining

5. 'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
Gaiole in Chianti
9.6 out of 10, Exceptional, (5 reviews)
"Georgeous clean home in home in an idyllic town! We had a fantastic stay here. I would very happily return."
Germany
Mariah M.
The price is AED 1,015
AED 1,158 total
includes taxes & fees
2 Sep - 3 Sep
'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
Property grounds

6. "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, (9 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is AED 6,977
AED 7,078 total
includes taxes & fees
13 Aug - 14 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Outdoor dining

7. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very Good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveler
The price is AED 4,445
AED 5,236 total
includes taxes & fees
7 Aug - 8 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

8. 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
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Exterior

9. 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 AED 1,498
AED 1,515 total
includes taxes & fees
11 Aug - 12 Aug
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Exterior

10. 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 AED 1,653
AED 1,670 total
includes taxes & fees
23 Aug - 24 Aug
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

11. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (37 reviews)
"Great spot"
Canada
Philippe
The price is AED 633
AED 697 total
includes taxes & fees
10 Aug - 11 Aug
Villa di Sotto
Lounge

12. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is AED 330
AED 380 total
includes taxes & fees
6 Aug - 7 Aug
Mariani Bed & Breakfast
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

13. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is AED 462
AED 516 total
includes taxes & fees
18 Aug - 19 Aug
Borgo di Erboli
Aerial view

14. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is AED 611
AED 689 total
includes taxes & fees
9 Aug - 10 Aug
Villa Curina Resort
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

15. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is AED 450
AED 511 total
includes taxes & fees
30 Aug - 31 Aug
Residenzia del Sogno
Exterior detail

16. 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 AED 342
AED 672 total
includes taxes & fees
7 Aug - 8 Aug
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Outdoor pool

17. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very Good, (56 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
Villa Rosa Panzano
Exterior

18. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (328 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is AED 371
AED 420 total
includes taxes & fees
11 Aug - 12 Aug
Hu Norcenni Girasole Village
Studio, Patio, Ground Floor | Terrace/patio

19. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (54 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is AED 402
AED 460 total
includes taxes & fees
6 Aug - 7 Aug
Fullino Nero
Apartment, 3 Bedrooms | Living area

20. Appartamento vicino al Duomo

Appartamento vicino al Duomo
Siena City Centre
10.0 out of 10, Exceptional, (1 review)
"Excellent location. Comfortable beds. Good value for money. Sufficient supplies, plates, pots, pans, etc. Internet worked well."
United States
Sandra
Appartamento vicino al Duomo
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

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."
Nicholas 7-night trip
Posted 14 hours ago
Borgo Scopeto Wine & Country Relais

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 26 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 Terme Antica Querciolaia. 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.