Chianti Region Vacation Rentals

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Nov 10 - Nov 11
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Nov 11 - Nov 12
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Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Chianti Region

2 bedrooms, cribs/infant beds, bed sheets
hu Firenze Certosa camping in town

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
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

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
$71 nightly
The price is $81
Nov 23 - Nov 24
Total with taxes and fees
Chianti Village Morrocco
Seasonal outdoor pool
Camping Village Il Poggetto

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
Aerial view
Relais Villa Olmo

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
$116 nightly
The price is $132
Dec 2 - Dec 3
Total with taxes and fees
Relais Villa Olmo
Exterior
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Castellina in Chianti
10.0 out of 10, Exceptional, (145)
"Everything was perfect: thank you"
United Kingdom
Richard D.
Farmhouse in the heart of the real chiantishire
Outdoor dining
Villa with large garden in the Chianti hills

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
Front of property - evening/night
Villa Il Palagio

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

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

San Casciano in Val di Pesa
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.
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
$106 nightly
The price is $118
Nov 11 - Nov 12
Total with taxes and fees
Relais Villa Belvedere
Outdoor dining
Villa with concierge service & heated pool at 20 minute from Florence center

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.
$1,545 nightly
The price is $1,550
Nov 23 - Nov 24
Total with taxes and fees
Villa with concierge service & heated pool at 20 minute from Florence center
Full-size fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

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

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

Beautiful villa for 6 people with WIFI, A/C, 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 WIFI, A/C, private pool, TV, patio and pets allowed
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

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

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

Montespertoli
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
Interior detail
Castello di Montegufoni

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
Interior
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

Greve in Chianti
9.0 out of 10, Wonderful, (24)
"excellent"
United States
David S W.
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Pool
Your panoramic house in Tuscany between vineyards and olive groves.

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.
Seasonal outdoor pool, pool umbrellas, sun loungers
Castello Del Nero - Podere San Filippo

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
Outdoor pool, pool umbrellas, sun loungers
Riserva di Fizzano Residence

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
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

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Clean room, courteous staff, and good winery"
Sangchun 1-night trip
Posted 4 days ago
Castello di Fonterutoli Wine Resort

Find out more about Chianti Region

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.

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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 $81 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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