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, (55)
"The only thing I would change is to make more stroller accessible "
United States
Aliana Paola
hu Firenze Certosa camping in town

Chianti Village Morrocco

3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Really enjoyed our short stay. The studio has all we needed, and we were given ine with a wraparound balcony with views of the stunning countryside!"
United Kingdom
Heike
Chianti Village Morrocco

Camping Village Il Poggetto

3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (65)
"Lovely camp site, with friendly staff. "
United Kingdom
Phillip
Camping Village Il Poggetto

Relais Villa Olmo

Impruneta
9.4 out of 10, Exceptional, (226)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
United States
Cameron
The price is €148
includes taxes & fees
12 Nov - 13 Nov
Relais Villa Olmo

Villa with large garden in the Chianti hills

Siena
9.6 out of 10, Exceptional, (75)
"Adrianna was very helpful. And her home was comfortable for our family of four,. The garden was beautiful and we ate outdoors every meal. The pool was clean, yet well loved. Thanks for a great stay in a perfect location to see the surrounds of Tuscany."
Australia
Fiona F.
Villa with large garden in the Chianti hills

Villa Il Palagio

Rignano sull'Arno
8.6 out of 10, Excellent, (59)
"Very nice atmosphere, felt very private, great price"
United States
Robert M
Villa Il Palagio

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
The price is €102
includes taxes & fees
10 Nov - 11 Nov
Relais Villa Belvedere

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

impruneta
10.0 out of 10, Exceptional, (105)
"The villa is absolutely stunning & our stay was an amazing experience. We had a small wedding ceremony with our guests followed by a home cooked Italian dinner which was the most perfect evening. Cate & her family were very accommodating and made us feel very welcome. Cate made our stay stress-free and was more than happy to help organise anything we may have needed for our stay. I can’t wait to stay again "
Australia
Ashleigh R.
The price is €1,379
includes taxes & fees
23 Nov - 24 Nov
Villa with concierge service & heated pool at 20 minute from Florence center

Rocca Palazzaccio

3.0 star property
Impruneta
9.0 out of 10, Wonderful, (13)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
Rocca Palazzaccio

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

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

Cavriglia
10.0 out of 10, Exceptional, (13)
"We had a really good time at this property. Everything was very clean and it was well equipped for what we wanted. It was very hot whilst we were there, so the air con and pool were very much appreciated! The town itself has several decent restaurants (so no need to cook, if you dont want to!) and there are some local buses but a car is needed really to make the most of the wider surrounding area (including the beautiful pool).The owners were very welcoming and extremely helpful with any queries...
United Kingdom
SimonandSue R.
Beautiful villa for 6 people with A/C, WIFI, private pool, 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)
"This was a trip we soon won't forget and we will 100% be back to visit. We <3 Isola Serena!!"
United States
Ashley M.
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

Your panoramic house in Tuscany between vineyards and olive groves.

Barberino Val d'Elsa
9.8 out of 10, Exceptional, (43)
"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!"
United States
Kerry P.
Your panoramic house in Tuscany between vineyards and olive groves.

Castello Del Nero - Podere San Filippo

Barberino Tavarnelle
9.8 out of 10, Exceptional, (38)
"We loved our stay here. The rooms were clean and updated. All the amenities you need are provided. The pool and the views by it are amazing and the area is quiet. The small town nearby has great food options. Would definitely stay again."
United States
Vincent
Castello Del Nero - Podere San Filippo

Riserva di Fizzano Residence

3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (23)
"The perfect hilltop retreat surrounded on all sides by vineyards and rolling hills with beautiful villas. Place was magical. Food was out of this world. Congratulations to the chef! Some of the best I've ever had. Perfect place to stay. "
United States
Elizabeth
Riserva di Fizzano Residence

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

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

Casa Vacanze Squarcialupi

Castellina in Chianti
8.0 out of 10, Very good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is €114
includes taxes & fees
10 Nov - 11 Nov
Casa Vacanze Squarcialupi

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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Top Chianti Region Hotel Reviews

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 €102 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.