Photo by Karen Dean

Holiday Rentals in Gaiole in Chianti

  • 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

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Gaiole in Chianti

Chianti Holiday House, private jacuzzi up to 6 pax

9.4 out of 10, Exceptional, (19)
"• Pros: Beautiful grounds, garden and hot tub; dishwasher was greatly appreciated, lovely views, excellent Instructions to reach the village. Cons: • Internet/cell connectivity in village is poor and upon arrival, couldn’t connect with cell phone OR my portable wifi. I couldn’t reach the owners, and had no photos to identify the house was ours, and instructions were incomplete. Had to knock on doors which was awkward. • Password for the wifi is wrong. Passwords are case-sensitive! This wasted a...
Chianti Holiday House, private jacuzzi up to 6 pax

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1323)
"We stayed in a 2 bedroom, 2 bath unit with a small kitchenette. There was a laundramat on site which was great. It us conveniently located if you have a car. The kitchenette had a small refrigerator, a mucrowave, and a cooktop. No oven. "
The price is €63
includes taxes & fees
6 Mar - 7 Mar
Hu Firenze Camping In Town

Relais Villa Olmo

9.4 out of 10, Exceptional, (200)
"My family and I stayed there for 2 nights, at the family suite. It was very clean and well decorated & furnished, with private pool and garden. The environment and view were good, staff were helpful, buffet breakfast got lot of choices. Highly recommended this lovely place "
The price is €123
includes taxes & fees
28 Feb - 1 Mar
Relais Villa Olmo

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (151)
"Wonderful location!!! Everything within walking distance. Friendly staff, clean modern room. Shower needs repairing. Will definitely return to stay here. If you are driving to the hotel, It’s a ZTL zone so contact the hotel to make arrangements for your car to be garaged. Don’t need a car here. It is in the best location!!!"
The price is €154
includes taxes & fees
28 Feb - 1 Mar
Il Battistero Siena - Residenza d'Epoca

san gimignano apartment in historical center, courtyard and fast free wifi

9.6 out of 10, Exceptional, (28)
"Amazing place with great location "
The price is €115
includes taxes & fees
28 Feb - 1 Mar
san gimignano apartment in historical center, courtyard and fast free wifi

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village

Typical Tuscan Residence near the farm la Vialla

9.8 out of 10, Exceptional, (6)
"Es ist das letzte Haus an der Straße in dem kleinen Ort, also kein Verkehr, nur Ruhe😌. Das Haus war sauber und ordentlich👍. Wir sind angekommen und haben uns gleich wohl gefühlt. Die Gastgeber sind sehr freundlich und hilfsbereit. Sie haben uns sehr gute Empfehlungen von sehenswerten in der Nähe geschickt, welche perfekt auf uns gepasst haben. Es war alles in allem eine sehr schöne Woche. Vielen Dank!!!😁"
Typical Tuscan Residence near the farm la Vialla

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (34)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.

ApartHotel Anghel

8.2 out of 10, Very good, (311)
"Nice place, quiet and clean!"
The price is €83
includes taxes & fees
13 Mar - 14 Mar
ApartHotel Anghel

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

Family-friendly Cottage in authentic stone style Swimmingpool Wine Relax Wif

9.2 out of 10, Wonderful, (22)
"This is an absolutely private place in the Tuscany’s hills. You can relax all day, but if you want the hustle and bustle of the city, Arezzo is the nearest big city (Siena 1.5 hours by car). There are several restaurants to choose nerby. A major shopping centre is 20-30 minutes away. The house is typical Tuscan style and well equipped, energy consumption needs attention but we had no problem. The big pool was our favourite, we spent almost the whole day there, there’s not much else to do on a...
Family-friendly Cottage in authentic stone style Swimmingpool Wine Relax Wif

House / Villa - Monte San Savino

9.8 out of 10, Exceptional, (16)
"Es erwartet dich ein hübsches Häuschen mitten in der Natur. Etwas abgelegen, wir mochten es genau so. Natur und Ruhe pur. Die Inneneinrichtung ist schon etwas in die Jahre gekommen, aber es ist alles da was man braucht. "
House / Villa - Monte San Savino

Riserva di Fizzano Residence

3.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing stay and experience. The property is well maintained and very peaceful. Everyone on the staff is friendly and very excited to have you as a guest. Food was wonderful. 5 stars all around. Convenient location for day trips or to just relax by the pool. Highly recommend"
Riserva di Fizzano Residence

Villa Il Palagio

8.8 out of 10, Excellent, (50)
"Thank you all is perfect"
Villa Il Palagio

Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

9.8 out of 10, Exceptional, (92)
"Anna was just a delightful host - because we came in late, we asked if she could provide us a simple meat/cheese tray (at our cost of course) and she provided a 4 course home made meal!!!! It was fantastic and we ate leftovers for our entire stay. The villa is just beautiful and had everything we needed and more - be sure to come in warm weather to use the pool. It's a perfect home base to explore the area - but be prepared to drive the curvy roads - which is half the fun! "
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

Bosco della Spina

9.4 out of 10, Exceptional, (142)
"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/ "
The price is €69
includes taxes & fees
6 Mar - 7 Mar
Bosco della Spina

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

9.4 out of 10, Exceptional, (51)
"Great host, location as we wanted in Tuscany. We had villa for only our family and it was enjoyable. It is a good WiFi there, TV, kitchen. And everything you need. "
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (58)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.

Regis Condo

9.2 out of 10, Wonderful, (55)
"This place is huge, two bathrooms, sitting area, kitchen. The staff gave good instructions and were very responsive. Very close to the main cathedral. "
The price is €88
includes taxes & fees
5 Mar - 6 Mar
Regis Condo

La Terrazza Sul Campo Rooming House

9.6 out of 10, Exceptional, (221)
"Absolutely fabulous! The room was large and came with a view of the Campo. No balcony on our unit, but our next door neighbor had a large one overlooking all of the activity in the Campo. Bout host and her staff were attentive yet invisible, and ensured the self service coffee and snack area was fully stocked and attractively prepared. The apartment entry was nestled in a quaint courtyard off the main shopping and restaurant street and provided easy access to all of the sights Siena has to...
The price is €129
includes taxes & fees
10 Mar - 11 Mar
La Terrazza Sul Campo Rooming House
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

Castello di Tornano Wine Resort

9.0 out of 10, Wonderful, (78)
"This was an absolute highlight of our trip. The castle is beautiful and incredibly well kept. The proprietor visited our table one morning, at the beautiful breakfast they offered, and gave us some fantastic history of the property and the upgrades she has made to the castle and the grounds. Nothing short of excellent!"
Castello di Tornano Wine Resort
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?

Typical Tuscan Residence near the farm la Vialla: This holiday home rental outside of Gaiole in Chianti is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and 1 hot tub.

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 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.