Holiday Rentals in Chianti Region

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Holiday Rentals in Chianti Region

hu Firenze Certosa camping in town

Impruneta
8.0 out of 10, Very good, (56)
"Wonderful staff and great amenities!"
Canada
Chenjin
hu Firenze Certosa camping in town

Relais Villa Olmo

Impruneta
9.4 out of 10, Exceptional, (227)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
The price is €124
includes taxes & fees
2 Dec - 3 Dec
Relais Villa Olmo

Chianti Village Morrocco

3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
The price is €98
includes taxes & fees
24 Nov - 25 Nov
Relais Villa Belvedere

Camping Village Il Poggetto

3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (65)
"Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant "
Australia
Rebecca
Camping Village Il Poggetto

Villa with large garden in the Chianti hills

Siena
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills

Villa with concierge service & heated pool at 20 minute from Florence center

impruneta
10.0 out of 10, Exceptional, (105)
"Our host (Cate), along with her sister and mother, were fantastic. Very responsive, easy to get ahold of and worked very hard to ensure our visit was amazing. Cate was onsite and worked closely with the catering company and made sure all went well.."
Canada
Tom A.
The price is €1,379
includes taxes & fees
23 Nov - 24 Nov
Villa with concierge service & heated pool at 20 minute from Florence center

Stunning villa for 6 guests with private pool, WIFI, A/C, TV, patio and pets allowed

Cavriglia
10.0 out of 10, Exceptional, (13)
"Really great stay here.The villa is absolutely beautiful on the outside and inside.Parking was easy (right in front of property).Location was beautiful and hosts were great."
United States
Mohammed S.
Stunning villa for 6 guests with private pool, WIFI, A/C, TV, patio and pets allowed

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

Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
Netherlands
Jochem G.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castello di Montegufoni

Montespertoli
8.0 out of 10, Very good, (31)
"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "
United States
Cheryl
Castello di Montegufoni

Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Greve in Chianti (Firenze)
10.0 out of 10, Exceptional, (42)
"Elena and her staff were excellent. They provided us with a welcome dinner which was great after our long trip in, as well as breakfast the next morning. Property is beautiful up in top of a hill overlooking the beautiful landscape. We had 9 people with more than enough room for all of us. Highly recommended!"
United States
Ryan F.
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Villa Il Palagio

Rignano sull'Arno
8.6 out of 10, Excellent, (60)
"We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great"
United States
Rebekkah
Villa Il Palagio

Castello Del Nero - Podere San Filippo

Barberino Tavarnelle
9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveller
Castello Del Nero - Podere San Filippo

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Ruffoli
9.8 out of 10, Exceptional, (58)
"Great location in the heart Chianti. The host was very welcoming and the apartment was perfect. very comfortable bed and very quiet location. Nice terrace and pool but unfortunately the weather wasnt warm enough for us to enjoy the pool. There is a dirt road to get to the apartment but very easy to navigate so dont be worried about it. Thank you Babette, we hope to have the pleasure of going back sometime."
United States
Andre P.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Riserva di Fizzano Residence

3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (23)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
Riserva di Fizzano Residence

Your panoramic house in Tuscany between vineyards and olive groves.

Barberino Val d'Elsa
9.8 out of 10, Exceptional, (43)
"The property was absolutely charming. It really had that homey, Italian, Tuscan charm about it. The kids and my husband loved it too. I wish I had planned for more days there. We didn’t have time to partake in the cooking class or truffle hunting, but I guess that just leaves a reason to come back. The location was great too because it’s in the country away from the busy cities, but a close enough drive to all the various Tuscan sites.The owners were very nice and spoke good enough English....
United States
Gwen L.
Your panoramic house in Tuscany between vineyards and olive groves.

Private villa in the heart of chianti with view of siena

Fonterutoli
10.0 out of 10, Exceptional, (3)
"Beautiful villa and stunning location. The host was very responsive and helpful. I would love to return someday. "
United States
Wendy F.
Private villa in the heart of chianti with view of siena

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is €155
includes taxes & fees
24 Nov - 25 Nov
Relais Villa Belpoggio - Residenza d'Epoca

Palazzo Pacini

Colle di Val d'Elsa
9.8 out of 10, Exceptional, (98)
"Such a beautiful gem of a hotel. Steeped in Florentine style. Comfortable and classy. Definitely would recommend "
United States
George
The price is €135
includes taxes & fees
23 Nov - 24 Nov
Palazzo Pacini

Villa San Filippo

4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (40)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
Villa San Filippo
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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Find out more about Chianti Region

Everything you need to know about Chianti Region 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 Chianti Region holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Chianti Region holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chianti Region holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chianti Region 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 Chianti Region holiday rentals we have selected for you start as low as €98 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chianti Region rentals

At Expedia, we put the best Chianti Region 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 Chianti Region 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 Chianti Region 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 Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.