Chianti Region Holiday Rentals

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Holiday Rentals in Chianti Region

hu Firenze Certosa camping in town

8.0 out of 10, Very good, (45)
"Hu Firenze Certosa is a nice retreat from the bustling tourist center. The swimming pool is nice, it is affordable, the rooms are nice and staff is great. "
hu Firenze Certosa camping in town

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (306)
"Great friendly fun camp site"
Hu Norcenni Girasole Village

Relais Villa Olmo

9.4 out of 10, Exceptional, (223)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
The price is NZ$437
includes taxes & fees
28 Sept - 29 Sept
Relais Villa Olmo

Camping Village Il Poggetto

3.0 star property
8.0 out of 10, Very good, (60)
"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 "
The price is NZ$111
includes taxes & fees
11 Oct - 12 Oct
Camping Village Il Poggetto

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

10.0 out of 10, Exceptional, (63)
"We had booked the villa for our wedding week to host 23 of our closest friends and family. It exceeded expectations in everyway, the views are breathtaking, the outside living areas are perfect for hosting large lunches and dinners, all the rooms are beautiful, and Raffaella and her team made sure we had everything we needed and more during our stay. It is so peaceful and quiet to enjoy the true beauty of Tuscany but also so close to the local town for dinners and shopping. The list of...
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Villa with large garden in the Chianti hills

9.6 out of 10, Exceptional, (73)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

10.0 out of 10, Exceptional, (119)
"We spent 2 weeks in this beautiful villa with close access to Florence and the easy trains of Italy. Bea and Jacapo were wonderful hosts and meals at the villa were delicious. The pool was a great relief at the end of warm and busy traveling days. We highly recommend this beautiful villa. "
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

Chianti Village Morrocco

3.0 star property
8.6 out of 10, Excellent, (103)
"Front desk was very helpful and very comfortable room. "
Chianti Village Morrocco

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (142)
"What a view! This location was all that we were hoping for. Thank you! "
Farmhouse in the heart of the real chiantishire

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (42)
"Very spacious and clean villa in between Florence and Siena in the heart of Chianti. Tremendous hosts that communicated often and met a couple special requests. Have already referred this listing and will definitely come back!"
Your panoramic house in Tuscany between vineyards and olive groves.

Relais Villa Belvedere

9.2 out of 10, Wonderful, (67)
"2 nights in Tuscany, about 30 minutes south of Florence. We wanted a quiet, country place that wasn't in the city, & it was fantastic! 2-story, beautiful grounds, very nice pool surrounded by flowering bushes, and a great breakfast."
The price is NZ$197
includes taxes & fees
12 Oct - 13 Oct
Relais Villa Belvedere

Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

10.0 out of 10, Exceptional, (80)
"Our family of eight spent twelve days at Villa Le Colline. The Villa was the perfect location from which to tour various areas of Italy. We could not have been more pleased. The home, grounds and views are much more beautiful than the pictures showed! It was a wonderful stay, and we would highly recommend this Villa for large families spending several days in the area. "
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Riserva di Fizzano Residence

3.0 star property
9.8 out of 10, Exceptional, (22)
"We had 2 beautiful days here in Chianti. Lovely property with a very good restaurant. Stunning views over the vineyards and Tuscany hills. Close drive to interesting cites. And the wine.... love to come back, and can absolutely recomend a stay here."
The price is NZ$389
includes taxes & fees
12 Oct - 13 Oct
Riserva di Fizzano Residence

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

10.0 out of 10, Exceptional, (42)
"We celebrated our 25th wedding anniversary with friends. It was a beautiful property with the most amazing views. This family owned and operated property was well taken care of. The service was exceptional."
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

9.4 out of 10, Exceptional, (66)
"The Leoni Villa is the perfect spot for a family vacation. There were 14 of us from 2 years old to 65 years old and we all had a great time! The rooms are great as well as the grounds which offers lemon, plum and olive trees. The Villa also has a spectacular pool with great views. Marco the caretaker was wonderful and helped us with anything we needed."
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano

Castello Del Nero - Podere San Filippo

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

Agriturismo La Ferrozzola

9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
Agriturismo La Ferrozzola

Palazzo Pacini

9.8 out of 10, Exceptional, (96)
"The owners of this hotel are very accommodating. The breakfast was very good. The restaurants around this hotel are plentiful and offer good value and views."
The price is NZ$293
includes taxes & fees
8 Oct - 9 Oct
Palazzo Pacini

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

9.8 out of 10, Exceptional, (51)
"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."
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
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

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, 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 NZ$111 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. 

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