Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chianti Region holiday rentals

A stone building with a patio area featuring a table and chairs under a large umbrella.

1. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (275 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is RM370
RM421 total
includes taxes & fees
23 Nov - 24 Nov
Relais Villa Olmo - Place of Charme
A table with breakfast items and a view of rolling hills.

2. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is RM294
RM333 total
includes taxes & fees
11 Nov - 12 Nov
Chianti Village Morrocco
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

3. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is RM522
RM593 total
includes taxes & fees
28 Nov - 29 Nov
Agriturismo La Ferrozzola
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

4. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 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 RM353
RM498 total
includes taxes & fees
1 Dec - 2 Dec
Antica Pieve B&B
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

5. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is RM425
RM474 total
includes taxes & fees
8 Nov - 9 Nov
Relais Villa Belvedere
An arched entrance with a lantern above, flanked by two potted plants.

6. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is RM651
RM735 total
includes taxes & fees
3 Dec - 4 Dec
Villa il Fedino
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

7. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is RM1,059
RM1,184 total
includes taxes & fees
10 Nov - 11 Nov
Terre di Baccio
A two-story house with a patio area, potted plants, and outdoor furniture.

8. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is RM591
RM669 total
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

9. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"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 RM468
RM543 total
includes taxes & fees
6 Nov - 7 Nov
Casa Vacanze Squarcialupi
A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

10. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is RM479
RM536 total
includes taxes & fees
3 Dec - 4 Dec
Palazzo Pacini
A stone building with a yellow sign reading "b&b erioico".

11. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is RM526
RM615 total
includes taxes & fees
6 Nov - 7 Nov
L' Eroico
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

12. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (174 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is RM309
RM395 total
includes taxes & fees
8 Nov - 9 Nov
I Parigi Corbinelli
A tented room with a bed, curtains, and a view of an outdoor deck.

13. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (125 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is RM196
RM229 total
includes taxes & fees
6 Nov - 7 Nov
hu Firenze Certosa camping in town
A stone building with a wooden door, a grill outside, and a stone wall.

14. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
Teranga in Chianti - Parking & Garden 3 BR
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

15. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is RM473
RM539 total
includes taxes & fees
6 Nov - 7 Nov
B&B La Fonte del Machiavelli
A swimming pool with a stone fountain, surrounded by a grassy area and trees.

16. Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.2 out of 10, Wonderful, (15 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 RM215
RM816 total
includes taxes & fees
8 Nov - 9 Nov
Rocca Palazzaccio
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

17. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
9.6 out of 10, Exceptional, (5 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is RM260
RM414 total
includes taxes & fees
9 Nov - 10 Nov
Borgo Antico Residence
A cozy living room with a stone wall, a wine rack, and two sofas.

18. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is RM390
RM429 total
includes taxes & fees
8 Nov - 9 Nov
Villa Cassia di Baccano
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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