Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Chianti Region vacation rentals

Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ₩239,276
₩263,204 total
includes taxes & fees
May 18 - May 19
Villa Cassia di Baccano
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"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
The price is ₩300,157
₩333,633 total
includes taxes & fees
May 17 - May 18
Riserva di Fizzano Residence
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (30 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is ₩239,552
₩263,507 total
includes taxes & fees
Apr 29 - Apr 30
Villa di Sotto
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is ₩343,545
₩384,822 total
includes taxes & fees
Apr 28 - Apr 29
Villa il Fedino
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is ₩177,291
₩198,481 total
includes taxes & fees
May 3 - May 4
Palazzo Pacini
View from property

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is ₩188,776
₩249,187 total
includes taxes & fees
May 17 - May 18
Antica Pieve B&B
Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
The price is ₩244,792
₩283,122 total
includes taxes & fees
May 7 - May 8
L' Eroico
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is ₩391,557
₩444,557 total
includes taxes & fees
Apr 30 - May 1
Borgo Argenina
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (238 reviews)
"We had an excellent stay, the staff is very friendly, stunning location and easy but windy road into Florence "
United States
Juliana
The price is ₩245,411
₩275,143 total
includes taxes & fees
Apr 28 - Apr 29
Relais Villa Olmo
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ₩204,195
₩233,266 total
includes taxes & fees
Apr 28 - Apr 29
Antico Borgo il Cardino
Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (41 reviews)
"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
The price is ₩157,570
₩183,710 total
includes taxes & fees
Apr 30 - May 1
Villa San Filippo
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is ₩212,376
₩247,458 total
includes taxes & fees
Apr 28 - Apr 29
Villa Curina Resort
Courtyard

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (165 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is ₩193,938
₩234,098 total
includes taxes & fees
Apr 29 - Apr 30
I Parigi Corbinelli
Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (77 reviews)
"Very comfortable stay. "
United States
Victor
The price is ₩451,085
₩510,038 total
includes taxes & fees
May 12 - May 13
Borgo Argiano
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ₩156,919
₩179,536 total
includes taxes & fees
May 25 - May 26
Mariani Bed & Breakfast
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ₩186,812
₩212,415 total
includes taxes & fees
Apr 28 - Apr 29
B&B La Fonte del Machiavelli
Exterior

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.4 out of 10, Exceptional, (26 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is ₩181,227
₩206,271 total
includes taxes & fees
May 10 - May 11
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Seasonal outdoor pool, pool umbrellas, sun loungers

Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.0 out of 10, Wonderful, (14 reviews)
"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
The price is ₩127,241
₩359,377 total
includes taxes & fees
Apr 29 - Apr 30
Rocca Palazzaccio
Exterior

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
9.2 out of 10, Wonderful, (28 reviews)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is ₩228,110
₩264,762 total
includes taxes & fees
Apr 28 - Apr 29
Rocca di Castagnoli
Daily buffet breakfast (EUR 12.50 per person)

Residence Poggio del Golf

Residence Poggio del Golf
Impruneta
9.2 out of 10, Wonderful, (11 reviews)
"À 20 minutes de Florence très bien et agréable Personel très Shympa tique "
France
Jean philippe
The price is ₩352,237
₩392,651 total
includes taxes & fees
May 19 - May 20
Residence Poggio del Golf
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

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"Amazing hotel with breathtaking views of the Chianti region landscape. Staff was incredibly helpful in providing the best wineries and restaurants to visit . This is the hotel to stay when visiting the Chianti region."
Eddy 3-night trip
Posted 1 day ago
Salvadonica - Borgo del Chianti

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