Photo by Karen Dean

Gaiole in Chianti Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Gaiole in Chianti

Farmhouse apartment in Chianti with garden and pool for 2 people
9.4 out of 10, Exceptional, (36)
"Wonderful hosts, quiet ancient setting Highly recommend"
Farmhouse apartment in Chianti with garden and pool for 2 people
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
8.8 out of 10, Excellent, (3)
"Property is off the beaten track so very peaceful. La Luna was a little small in the kitchen lounge area for 4 people (needs another sofa). Unfortunately we had a few issues that we told the manager about at the end of our stay in the hope that they will be sorted for future visitors. We couldn’t get the tv to work (only wanted to watch Euro football finals!), dishwasher wouldn’t work and the plug sockets were a nightmare with a need for a lot more adapters or extension leads that would fit the...
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1274)
"Overall our stay in Hu Firenze was great. The restaurant on location was really cool and tasted pretty great too. The staff was friendly and helpful. Our little house was a big tent basically. Interesting but annoying when people would come check it out or tap on our house (happened a couple times). It was kinda funny but always awkward. We had a bed, closet, mini fridge, and bathroom. They had a shuttle to take you partially into town or you could walk to Firenze Rovezzano (train station)....
The price is NZ$104
includes taxes & fees
18 Nov - 19 Nov
Hu Firenze Camping In Town
Hu Norcenni Girasole Village
4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (141)
"The service at this hotel was impeccable. We were running late for our wine tasting but they were still SO accommodating! The rooms were beautiful and the view from the hotel are amazing. It was super accessible to everything. Also, the parking options were great - highly recommend. They're so responsive through texting and it was great to have this level of service. Highly rec! "
The price is NZ$223
includes taxes & fees
18 Nov - 19 Nov
Il Battistero Siena - Residenza d'Epoca
Camping Village Il Poggetto
3.0 star property
8.0 out of 10, Very good, (41)
"Nice safe village with restaurant, bar and pool. Staff were excellent. "
Camping Village Il Poggetto
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
10.0 out of 10, Exceptional, (110)
"Wonderful location in Arezzo. The home itself is Amazing, Beautiful, Historic yet with Modern conveniences. Stefano, your host is so accommodating, incredibly helpful and is sure to make your stay perfect. If we could give it more ⭐️ stars we would!!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
ApartHotel Anghel
8.2 out of 10, Very good, (305)
"Nice place, quiet and clean!"
The price is NZ$150
includes taxes & fees
1 Dec - 2 Dec
ApartHotel Anghel
Relais Villa Olmo
9.4 out of 10, Exceptional, (195)
"Absolutely stunning oil and grape vineyard, the resort was beautiful and walkable into town for additional dining. Breakfasts hosted were lovely. Beautiful addition to our honeymoon in Italy. "
The price is NZ$221
includes taxes & fees
18 Nov - 19 Nov
Relais Villa Olmo
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
9.6 out of 10, Exceptional, (45)
"This property is several kilometers up a gravel road from Murlo, Italy. The road is okay but we got a little concerned after it had been raining for a while. The property is remote and near several hiking paths. It is great for people who want to get out and hike around the hills of Italy. The gardens are really nice. We would have spent more time outside if the weather had cooperated more. We went in the fall so it was getting a little cooler up in the hills. There was a nice fireplace that...
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Borgo Argiano
10.0 out of 10, Exceptional, (60)
"Very comfortable stay. "
Borgo Argiano
La Terrazza Sul Campo Rooming House
9.6 out of 10, Exceptional, (221)
"Excellent location. Excellent service. Great view from the balcony. "
The price is NZ$218
includes taxes & fees
1 Dec - 2 Dec
La Terrazza Sul Campo Rooming House
Camping Boschetto Di Piemma
3.0 star property
8.8 out of 10, Excellent, (71)
"Nice quiet spot in the woods but very close to San Gimignano. Very clean. Comfortable beds. They don’t provide towels or soaps, but that is clear up front. You can rent towels if you want and they sell soap/ shampoo in the office. "
Camping Boschetto Di Piemma
Bosco della Spina
9.4 out of 10, Exceptional, (141)
"We were met by the property owner who was pleasant and informative. The room was exactly as depicted in the photos and property was in excellent condition. We would recommend to anyone staying the area at any time of year/ "
Bosco della Spina
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Villa Il Palagio
8.8 out of 10, Excellent, (48)
"Thank you all is perfect"
Villa Il Palagio
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
10.0 out of 10, Exceptional, (95)
"Have you ever felt that you were at home when you knew you weren't ? That's the feeling we had when we stayed with Cate at her family home for two weeks. The property is absolutely exquisite. Every view is a painted picture. The house has lots of nooks and crannies for people to just relax. And her family was there at a moments notice if we needed anything. Cecilia, Cate sister is a spectacular chef, We ordered breakfast every morning and it was set up beautifully and certainly had more food...
The price is NZ$1,896
includes taxes & fees
13 Dec - 14 Dec
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (129)
"What can we say!!! We loved the little house….so much charm! The hosts were very easy to communicate with….the quietness and beauty of the property were just what we needed!! "
Farmhouse in the heart of the real chiantishire
"Villa le Ginestre": the better geographic position to visit the Tuscany.
9.8 out of 10, Exceptional, (71)
"Very panoramic place and very clean"
"Villa le Ginestre": the better geographic position to visit the Tuscany.
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (105)
"we had an amazing week at this villa with 18 family members, age 6 months to 87 years. Jacobo and Beatrice were so nice , very welcoming and super helpful with transportation and amenities nearby. If we had any problems we could easily text and Jacopo would immediately answer . i would recommend coming here ! Faboulous"
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
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.
Don't see what you're looking for?
See all available properties in Gaiole in Chianti
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Gaiole in Chianti you may be interested in

Castello di Spaltenna
5.0 star property
9.6 out of 10, Exceptional, (219)
"Staff, spa and food was all perfect "
Castello di Spaltenna
Ultimo Mulino Wellness Country Hotel
4.0 star property
8.6 out of 10, Excellent, (114)
"Beautiful location and building. We had a great stay!"
Ultimo Mulino Wellness Country Hotel
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1274)
"Overall our stay in Hu Firenze was great. The restaurant on location was really cool and tasted pretty great too. The staff was friendly and helpful. Our little house was a big tent basically. Interesting but annoying when people would come check it out or tap on our house (happened a couple times). It was kinda funny but always awkward. We had a bed, closet, mini fridge, and bathroom. They had a shuttle to take you partially into town or you could walk to Firenze Rovezzano (train station)....
The price is NZ$104
includes taxes & fees
18 Nov - 19 Nov
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.

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?

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms : This holiday home rental outside of Gaiole in Chianti is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Gaiole in Chianti?

With 48 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.