Gaiole in Chianti Holiday Rentals

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Gaiole in Chianti holiday rentals

In-room safe, cots/infant beds, bed sheets
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1610)
"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town
Aerial view
Relais Villa Olmo

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (227)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
Relais Villa Olmo
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is HK$547
HK$638 total
includes taxes & fees
16 Dec - 17 Dec
ApartHotel Anghel
Cots/infant beds, bed sheets
hu Firenze Certosa camping in town

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.0 out of 10, Very good, (57)
"Wonderful staff and great amenities!"
Canada
Chenjin
hu Firenze Certosa camping in town
View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$546
HK$627 total
includes taxes & fees
12 Dec - 13 Dec
Tuscasì Aparthotel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Exterior
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire
Castellina in Chianti
10.0 out of 10, Exceptional, (148)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is HK$496
HK$564 total
includes taxes & fees
21 Dec - 22 Dec
Chianti Village Morrocco
Private kitchen
Regis Condo

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
The price is HK$727
HK$814 total
includes taxes & fees
18 Dec - 19 Dec
Relais Villa Belvedere
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is HK$1,100
HK$1,281 total
includes taxes & fees
12 Dec - 13 Dec
Il Poggio dell'Eremita
Fridge, microwave, oven, stovetop
Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (143)
"Beautiful property and great experience "
United States
edward p.
Luxury Villa in the Florentine hills
View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is HK$1,475
HK$1,659 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Property grounds
Typical Tuscan Countryside Cottage near Florence

Typical Tuscan Countryside Cottage near Florence

Typical Tuscan Countryside Cottage near Florence
Bagno a Ripoli, San Bartolomeo A Quarate
10.0 out of 10, Exceptional, (36)
"Magdalena was super helpful letting us know what places there were in the area! The cottage was a great place to stay, and looks better than the pictures! Absolutely an amazing place to stay!"
United States
Dylan K.
Typical Tuscan Countryside Cottage near Florence
Pool
Typical Tuscan Country House

Typical Tuscan Country House

Typical Tuscan Country House
Pelago
10.0 out of 10, Exceptional, (128)
"Beautiful home and gracious host!"
United States
Levi M.
Typical Tuscan Country House
Outdoor pool
CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms

CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms

CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms
San Casciano in Val di Pesa
10.0 out of 10, Exceptional, (124)
"Excellent property Great bedrooms and eating area"
United Kingdom
douglas f.
CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

Camping Siena Colleverde
3.0 star property
Scacciapensieri
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Outdoor pool
17th century farmhouse with private pool and Wi-Fi and air conditioning

17th century farmhouse with private pool and Wi-Fi and air conditioning

17th century farmhouse with private pool and Wi-Fi and air conditioning
Arezzo
9.2 out of 10, Wonderful, (39)
"We stayed as a family of 10 and had a great time. The accommodation is definitely rustic and traditional. It won’t suit everyone but if you’re looking to get back to basics look no further! For us as an Australian family it could have cleaner and we ended up doing cleaning ourselves to make it more comfortable. The bed linen and towels are also ready for a refresh. The host was great and provided a good summary of the local area and sights. Arezzo is a lovely day out. "
Australia
Anonymous traveller
17th century farmhouse with private pool and Wi-Fi and air conditioning
Outdoor dining
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills
2 bars/lounges
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma
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

Hotel Mulino di Firenze, WorldHotels Crafted

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent
"This hotel was one of the best we have ever stayed in. Despite our early arrival, the staff was able to accommodate us with a room right away. While we waited, we explored the property and were immediately impressed by the stunning views. Our bags were delivered to our room for us, allowing us to fully enjoy our time on the grounds. The staff was exceptionally helpful, and the housekeeping team did an outstanding job keeping our room spotless and ensuring our refrigerator was always stocked with water. Overall, the property offered breathtaking views, excellent cleanliness, and warm, friendly service. We loved every bit of it 10/10 recommend! "
Lesbia 3-night trip
Posted 2 days ago
Hotel Mulino di Firenze, WorldHotels Crafted

Find out more about Gaiole in Chianti

Search for holiday rentals in Gaiole in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in Gaiole in Chianti using one of the methods below:

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Look no further and take a look at our great range of rental properties in Gaiole in Chianti!

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 a coffee maker. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 29 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 Chianti Sculpture Park. 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.