Photo by Karen Dean

Gaiole in Chianti Holiday Rentals

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Holiday Rentals in Gaiole in Chianti

Farmhouse apartment in Chianti with garden and pool for 2 people
Outdoor pool

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
Fridge, microwave, oven, stovetop

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
Seasonal outdoor pool

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1291)
"Very clean and convenient (parking, supermarket, eatery, laundry, facilities for children, cooking in the chalet). The shuttle bus takes you to the main city centre in Florence where ponte vecchio and the plazas are located. "
The price is NZ$125
includes taxes & fees
20 Dec - 21 Dec
Hu Firenze Camping In Town
Il Battistero Siena - Residenza d'Epoca
Bar (on property)

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (144)
"Spectacular view from our balcony! Close to the Duomo and Piazza del Campo, great restaurants and shopping. Highly recommend!"
The price is NZ$290
includes taxes & fees
22 Dec - 23 Dec
Il Battistero Siena - Residenza d'Epoca
Relais Villa Olmo
Aerial view

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 "
Relais Villa Olmo
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Fridge, microwave, oven, stovetop

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

10.0 out of 10, Exceptional, (111)
"Where to begin? For starters this property is even more beautiful in person than in the incredible photos shown here. It is very clean. The kitchen is fully equipped. Many people had left helpful cooking ingredients. The location is perfect. We were right across the street from a multi-generational, family owned & operated pastry/coffee shop. The women who run it are lovely, and the food/coffee was so yummy we went there every day of our weeklong stay. We easily walked to delicious restaurants,...
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
ApartHotel Anghel
Lobby lounge

ApartHotel Anghel

8.2 out of 10, Very good, (305)
"Nice place, quiet and clean!"
The price is NZ$146
includes taxes & fees
10 Jan - 11 Jan 2025
ApartHotel Anghel
Hu Norcenni Girasole Village
Exterior

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Outdoor pool

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
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

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
La Terrazza Sul Campo Rooming House
Suite | Balcony view

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$199
includes taxes & fees
8 Jan - 9 Jan 2025
La Terrazza Sul Campo Rooming House
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Outdoor pool, a heated pool, pool loungers

Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center

10.0 out of 10, Exceptional, (96)
"We had a fantastic stay at this lovely villa. We were a group of two families with four adults and four kids ages 5 to 13. Cate, the hostess, was extremely attentive and helped us arrange various activities during our stay. She helped us arrange a cooking class at the villa, a bike tour through Chianti region with a private wine tasting, and a chef cooking a Thanksgiving meal for us (we opted for Tuscan - not American food). We also got to tour a working olive mill. In addition, upon hearing...
The price is NZ$1,881
includes taxes & fees
20 Dec - 21 Dec
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Relais Villa Belvedere
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Relais Villa Belvedere

9.2 out of 10, Wonderful, (64)
"Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer."
The price is NZ$178
includes taxes & fees
7 Jan - 8 Jan 2025
Relais Villa Belvedere
Bosco della Spina
Exterior

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/ "
Bosco della Spina
"Villa le Ginestre": the better geographic position to visit the Tuscany.
Pool

"Villa le Ginestre": the better geographic position to visit the Tuscany.

9.8 out of 10, Exceptional, (72)
"The property is well located to discover many great Tuscan towns: San Gimignano, Volterra, Luca and Siena ; we went by train, only 10 euros return."
"Villa le Ginestre": the better geographic position to visit the Tuscany.
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Outdoor pool

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

9.8 out of 10, Exceptional, (98)
"This villa exceeded our expectations. It has ample room for a large family and was very neat and clean. The host was very attentive to all of our needs and very easy to communicate with. The location is just far enough away from Florence to give it a great Tuscan feel in the middle of a vineyard and olive orchard. I highly recommend this property. "
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Independent house in the hills of the Sienese countryside
Exterior

Independent house in the hills of the Sienese countryside

10.0 out of 10, Exceptional, (73)
"The picture of the farmhouse doesn't do the location justice after you see it in person.. it's a spectacular view! We arrived on a beautiful sunny day and were warmly welcomed by our hosts. After getting a quick tour of where we would be staying for the next week, we were pleasantly surprised by the kind gesture of homemade olive oil and wine left for us to have. Thank you! The location of this property is perfect for visiting the Tuscany countryside. Not only did we visit Siena on a few...
Independent house in the hills of the Sienese countryside
House with character in typical medieval borgo on the Chianti Classico hills
Outdoor dining

House with character in typical medieval borgo on the Chianti Classico hills

9.6 out of 10, Exceptional, (47)
"Our three year old granddaughter thought it was her castle and that she was a princess. Michele and Elisabetta remain exquisite hosts and the neighbors are very welcoming. Rental cars and train system allowed us to visit neighboring cites. Overall, a wonderful vacation!!!!"
House with character in typical medieval borgo on the Chianti Classico hills
Luxury Villa in the Florentine hills
Fridge, microwave, oven, stovetop

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (130)
"We loved our stay. From the start David sent all kinds of information. We had a few more questions about the bus and the area, David sent answers with in minutes with GPS maps. We loved the view, the Persimmon and Pomegranate from the trees in the yard were delicious. All of the bedrooms and bathrooms were awesome, everything was clean. We stayed at 3 other locations this trip and this was our favorite. My wife said the blow dryer was the best blow dryer in Italy."
The price is NZ$408
includes taxes & fees
5 Jan - 6 Jan 2025
Luxury Villa in the Florentine hills
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Pool

Villa Scopetello with Pool and Tennis court near Montepulciano and Siena

10.0 out of 10, Exceptional, (100)
"A wonderful setting, terrific location and ideal large house for our 3 generation group of extended family members. The 8 children under 11ys had a fantastic time playing with their cousins enjoying the grounds, pool area, tennis court and football goalposts. Sonja was a great host - relaxed but responsive and a thoughtful cook for the two prepared meals she made for us"
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
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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Other types of properties in Gaiole in Chianti you may be interested in

Castello di Spaltenna
Front of property - evening/night

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
Outdoor pool, free pool cabanas, pool umbrellas

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
Seasonal outdoor pool

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1291)
"Very clean and convenient (parking, supermarket, eatery, laundry, facilities for children, cooking in the chalet). The shuttle bus takes you to the main city centre in Florence where ponte vecchio and the plazas are located. "
The price is NZ$125
includes taxes & fees
20 Dec - 21 Dec
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?

Independent house in the hills of the Sienese countryside: This holiday home rental outside of Gaiole in Chianti is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Gaiole in Chianti?

With 46 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.