Photo by Karen Dean

Gaiole in Chianti Holiday Rentals

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Holiday Rentals in Gaiole in Chianti

Fridge, microwave, oven, stovetop
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
10.0 out of 10, Exceptional, (1)
"Enjoyed it"
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Pool
Farmhouse apartment in Chianti with garden and pool for 2 people
9.4 out of 10, Exceptional, (35)
"Wonderful hosts, quiet ancient setting Highly recommend"
Farmhouse apartment in Chianti with garden and pool for 2 people
Seasonal outdoor pool
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (967)
"4 out of 5.... Thanks "
The price is NZ$179
per night
26 May - 27 May
Hu Firenze Camping In Town
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Exterior
Hu Norcenni Girasole Village
4.0 star property
8.4 out of 10, Very good, (242)
"The location is really beautiful. There are constant shuttles to transport from one location to other within the property. Nice food options and music on specific days Clean Cabins If you have not booked shuttle from the Figline station to this place- you may have a hard time getting a taxi from the station. I recommend to plan ahead for the commute from the train station to this property."
The price is NZ$87
per night
4 Jun - 5 Jun
Hu Norcenni Girasole Village
Bar (on property)
Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (117)
"The staff is friendly and helpful, an asset to this hotel. "
The price is NZ$294
per night
5 Jun - 6 Jun
Il Battistero Siena - Residenza d'Epoca
Seasonal outdoor pool
Camping Village Il Poggetto
3.0 star property
7.8 out of 10, Good, (24)
"The staff is friendly and helpful. This is a nice place to stay . "
The price is NZ$120
per night
5 Jun - 6 Jun
Camping Village Il Poggetto
Fridge, microwave, oven, stovetop
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
10.0 out of 10, Exceptional, (101)
"Stephano goes out of his way to make his guests feel at home. The place was comfortable and spotless. We enjoyed getting to know our host and his city. The kitchen is well appointed with a well stocked wine rack. Read through the reviews, they are accurate! Comfortable bedding, lovely surroundings and, oh yes, a wonderful bakery across the street. Highly recommended!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Lobby lounge
ApartHotel Anghel
8.2 out of 10, Very good, (276)
"The postive is checkin experiene is easy as the receptionist is very nice. She communicated well. The negative is the room are not insulated. You can hear other rooms closing their doors and kids running in the hallway. "
The price is NZ$187
per night
24 Jun - 25 Jun
ApartHotel Anghel
Pool
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
9.6 out of 10, Exceptional, (38)
"The house is a beautiful old Italian house with high ceilings with wooden beams and tiled floors. Everything in the house worked pedfectly- wifi, hot water, screens on the windows, kitchen and bath. The house is set in the midst of the Tuscan hills with hikes starting right from the front door. The grounds in the nature preserve are lovely with local plantings. The hostess, Marina, was welcoming, helpful, and altogether delightful. The gravel access road is steep and curvy in places. We were...
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
Superior Mobile Home | Private kitchenette
Camping Boschetto Di Piemma
3.0 star property
9.0 out of 10, Wonderful, (56)
"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. "
The price is NZ$112
per night
27 May - 28 May
Camping Boschetto Di Piemma
Exterior
Bosco della Spina
9.4 out of 10, Exceptional, (123)
"Charming property in midst of magical Tuscany."
The price is NZ$171
per night
4 Jun - 5 Jun
Bosco della Spina
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (51)
"We looked at many properties, both online and during a December visit to Chianti. This villa was by far best location we found. Everything was perfect, from our communication with Serena, to the reception by Raffaella, and then a stay in an amazing villa in an amazing setting. We were a group of maximum 9 persons, ranging in age from 20 to 60, and all were pleased with the amenities, especially watching the sunset across the vineyards and hills of Tuscany from the terrace. We will be looking to...
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Front of property - evening/night
Villa Il Palagio
8.6 out of 10, Excellent, (24)
"A great suite. Reception can help with taxis to and from the local train station. Fast trains to Firenze / Florence. Restaurant only open for breakfast during the low season, so dinner is a bit of a mission: Reception helped with ordering pizza 🍕"
The price is NZ$290
per night
27 May - 28 May
Villa Il Palagio
Exterior
Family apartment with magical view on the old city, balcony, wifi & parking
9.8 out of 10, Exceptional, (35)
"The apartment is very spacious with lots of antiques and has a home from home feel. It is about a 20 min walk into town, uphill in places but straight forward. Parking is tight so bring a small car 😊. The views across to the old town are great and the balcony space a plus."
Family apartment with magical view on the old city, balcony, wifi & parking
Outdoor pool
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
9.8 out of 10, Exceptional, (84)
"Staying at a villa and property like this was a dream come true. As you’ve read the pictures just do not do it justice. The view is spectacular. Our host was so charming and helpful. We had a cooking class with Jacopo from "Let's Cook" which was so much fun. We also did a Chianti Wine and Food Safari with Walkabout tours that was fantastic. All of Caterina suggestions were so helpful even down to the drivers she recommended. Having this Villa to come home to each night was the icing on the cake."
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Pool
"Villa le Ginestre": the better geographic position to visit the Tuscany.
9.8 out of 10, Exceptional, (60)
"Very panoramic place and very clean"
"Villa le Ginestre": the better geographic position to visit the Tuscany.
Outdoor pool, a heated pool, pool loungers
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
10.0 out of 10, Exceptional, (85)
"Caterina and her family hosted us and made our trip unbelievable! They helped with transportation, travel ideas, and also prepared home cooked amazing meals in the villa, including two 4 course dinners and an amazing pizza night in the homes built in pizza oven. The grounds are absolutely gorgeous. Thank you for a wonderful stay! I’d definitely stay at this wonderful home again! Thank you Cate!"
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
Property grounds
House with character in typical medieval borgo on the Chianti Classico hills
9.6 out of 10, Exceptional, (44)
"A very beautiful property and grounds, in the middle of the Tuscan countryside The patio area with charcoal grill amongst the olive trees was a beautiful setting for snacks and meals The house inside was very rustic and authentic but comfortable and the kitchen and bathroom s are well equipped Our hosts were very friendly and the welcome bottle of wine and fresh fruit basket was a wonderful touch after a long day of travelling The neighbours were lovely we spoke to several of them though a...
House with character in typical medieval borgo on the Chianti Classico hills
Seasonal outdoor pool, pool umbrellas
Borgo San Lorenzo a Linari
8.4 out of 10, Very good, (87)
"Just a nice quiet property to enjoy some relaxation and close to Siena. Front desk agents were very nice and helped me efficiently. "
The price is NZ$309
per night
27 May - 28 May
Borgo San Lorenzo a Linari
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
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See all available properties in Gaiole in Chianti
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.

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

Front of property - evening/night
Castello di Spaltenna
5.0 star property
9.6 out of 10, Exceptional, (196)
"Amazing, relaxing, storybook stay. Wish we could have stayed longer!"
The price is NZ$623
per night
2 Jun - 3 Jun
Castello di Spaltenna
Outdoor pool, free pool cabanas, pool umbrellas
L'Ultimo Mulino
4.0 star property
8.6 out of 10, Excellent, (100)
"We had a very pleasant stay. Upscaled place with vintage vibes. Amazing views and excellent guest service. "
The price is NZ$289
per night
2 Jun - 3 Jun
L'Ultimo Mulino
Seasonal outdoor pool
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (967)
"4 out of 5.... Thanks "
The price is NZ$179
per night
26 May - 27 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gaiole in Chianti holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gaiole in Chianti. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gaiole in Chianti. Seeing all the best attractions is bound to make you fall in love with Gaiole in Chianti. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gaiole in Chianti short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Gaiole in Chianti?

With 49 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.

Recent reviews of Gaiole in Chianti properties
Expedia verified reviews