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

Gaiole in Chianti Holiday Rentals

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Gaiole in Chianti holiday rentals

Exterior

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 AU$244
includes taxes & fees
16 July - 17 July
L' Eroico
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is AU$556
includes taxes & fees
15 July - 16 July
Borgo Argenina
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (96 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is AU$113
includes taxes & fees
15 July - 16 July
Domus il Palio B&B
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (70 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is AU$246
includes taxes & fees
21 July - 22 July
Villa Curina Resort
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (38 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is AU$162
includes taxes & fees
15 July - 16 July
iConic Wellness Resort
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is AU$128
includes taxes & fees
3 Aug - 4 Aug
Artisti del Cavallo Tourism
Superior Mobile Home | Terrace/patio

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (86 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is AU$97
includes taxes & fees
5 Aug - 6 Aug
Camping Boschetto Di Piemma
City view from property

Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.0 out of 10, Very good, (17 reviews)
"Beautiful view from our room at the top"
United States
ralph
The price is AU$124
includes taxes & fees
27 July - 28 July
Birbo Bike Hospitality
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is AU$120
includes taxes & fees
17 July - 18 July
Villa Fontis Rapolano
Property amenity

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (72 reviews)
"Nice property, very reasonable price"
United States
Alex
The price is AU$107
includes taxes & fees
16 July - 17 July
Camping Village Il Poggetto.
Premium bedding, down duvets, pillow-top beds, individually furnished

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AU$140
includes taxes & fees
19 July - 20 July
Tuscasì Aparthotel
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is AU$219
includes taxes & fees
15 July - 16 July
B&B Palazzo Tortoli
Exterior

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is AU$138
includes taxes & fees
8 Aug - 9 Aug
Villa le Camelie Siena
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (189 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is AU$143
includes taxes & fees
20 July - 21 July
Cameracaffè Centro
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is AU$207
includes taxes & fees
21 July - 22 July
B&B La Fonte del Machiavelli
Breakfast, lunch and dinner served

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.6 out of 10, Exceptional, (38 reviews)
"Charming and very original. Great warmth from the staff and very helpful. Enjoyed the room and restaurant at and surrounding towns."
Australia
Con
The price is AU$269
includes taxes & fees
19 July - 20 July
La Locanda di Pietracupa
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
The price is AU$189
includes taxes & fees
15 July - 16 July
B&B Il Corso
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (102 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is AU$364
includes taxes & fees
3 Aug - 4 Aug
Villa il Fedino
Double Room (Ginevra) | View from room

A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
7.8 out of 10, Good, (29 reviews)
"Christiana was the perfect hostess. Accommodations were quaint. Rooms and common areas were spotless. Breakfast and cafe were amazing. A true gem located in the heart of Siena. Close to shops, restaurants, and enotecas. I highly recommend you stay. "
United States
Christina
The price is AU$199
includes taxes & fees
15 July - 16 July
A Casa Mastacchi
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (85 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is AU$84
includes taxes & fees
19 July - 20 July
hu Firenze Certosa 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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Staff and hotel was great. Breakfast was wonderful👍"
Peter 9-night trip
Posted 16 hours ago
Radisson Blu Hotel, Florence

Find out more about Gaiole in Chianti

Everything you need to know about Gaiole in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaiole in Chianti holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Gaiole in Chianti holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gaiole in Chianti. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gaiole in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gaiole in Chianti holiday rentals we have selected for you start as low as AU$84 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Gaiole in Chianti rentals

At Expedia, we put the best Gaiole in Chianti holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gaiole in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaiole in Chianti holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaiole in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 22 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.