Chianti Region Vacation Rentals

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Vacation Rentals in Chianti Region

hu Firenze Certosa camping in town
8.0 out of 10, Very Good, (54)
"The only thing I would change is to make more stroller accessible "
United States
Aliana Paola
$47 nightly
The price is $56
Nov 13 - Nov 14
Total with taxes and fees
hu Firenze Certosa camping in town
Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (107)
"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
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
Relais Villa Olmo
9.4 out of 10, Exceptional, (226)
"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
$117 nightly
The price is $132
Dec 1 - Dec 2
Total with taxes and fees
Relais Villa Olmo
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (143)
"Everything was perfect: thank you"
United Kingdom
Richard D.
Farmhouse in the heart of the real chiantishire
Villa with large garden in the Chianti hills
9.6 out of 10, Exceptional, (74)
"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
8.6 out of 10, Excellent, (59)
"Very nice atmosphere, felt very private, great price"
United States
Robert M
Villa Il Palagio
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (124)
"The accommodations were excellent with plenty of space for our group. The hosts were more than accommodating and helped with rental car arrangements and tour companies. They also were excellent cooks and we enjoyed many meals prepared by them. "
United States
David L.
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Relais Villa Belvedere
9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
$104 nightly
The price is $117
Dec 3 - Dec 4
Total with taxes and fees
Relais Villa Belvedere
Villa with concierge service & heated pool at 20 minute from Florence center
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.
$1,443 nightly
The price is $1,447
Nov 3 - Nov 4
Total with taxes and fees
Villa with concierge service & heated pool at 20 minute from Florence center
Rocca Palazzaccio
3.0 star property
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
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
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
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."
United States
Melissa M.
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Wonderful villa for 6 guests with private pool, WIFI, A/C, TV, patio and pets allowed
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.
Wonderful villa for 6 guests with private pool, WIFI, A/C, TV, patio and pets allowed
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
9.0 out of 10, Wonderful, (23)
"excellent"
United States
David S W.
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
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."
United States
Cynthia B.
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Your panoramic house in Tuscany between vineyards and olive groves.
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
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
9.8 out of 10, Exceptional, (23)
"We absolutely loved this hotel. The views were incredible and the dinner we had in the restaurant was amazing. The apartments are spacious and have everything you need except maybe some hair conditioner. The breakfast wasn’t the best I’ve ever had but fine with a decent selection. The staff are all super friendly and helpful. "
United Kingdom
Hayley
Riserva di Fizzano Residence
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
9.8 out of 10, Exceptional, (56)
"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
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

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Everything you need to know about Chianti Region vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chianti Region vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chianti Region in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $56 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chianti Region rentals

At Expedia, we put the best Chianti Region vacation 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 vacation.

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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