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Villa Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Villa holiday rentals

A stone building with a yellow sign reading "b&b erioico".

1. 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 S$197
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

2. 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 S$163
includes taxes & fees
11 Nov - 12 Nov
Casa Vacanze Squarcialupi
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

3. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is S$127
includes taxes & fees
23 Oct - 24 Oct
Mariani Bed & Breakfast
A stone building with a garden in front.

4. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is S$265
includes taxes & fees
19 Oct - 20 Oct
Borgo Argenina
A stone building with multiple windows and a chimney.

5. 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 S$186
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A spacious living area with a high ceiling, a staircase, and a large window.

6. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is S$171
includes taxes & fees
19 Oct - 20 Oct
Villa Curina Resort
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

7. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is S$173
includes taxes & fees
16 Oct - 17 Oct
Residenzia del Sogno
A table with breakfast items and a view of rolling hills.

8. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is S$113
includes taxes & fees
16 Oct - 17 Oct
Chianti Village Morrocco
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

9. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is S$236
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

10. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is S$247
includes taxes & fees
19 Oct - 20 Oct
Riserva di Fizzano Residence
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

11. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is S$126
includes taxes & fees
28 Oct - 29 Oct
Villa San Filippo
A dining area with a table set for two, featuring a view of greenery through a window.

12. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is S$198
includes taxes & fees
13 Nov - 14 Nov
La Locanda di Pietracupa
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

13. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is S$221
includes taxes & fees
19 Oct - 20 Oct
Relais Villa Belpoggio - Residenza d'Epoca
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

14. 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 S$143
includes taxes & fees
23 Oct - 24 Oct
Relais Villa Belvedere
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

15. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 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 S$388
includes taxes & fees
16 Oct - 17 Oct
Terre di Baccio
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

16. 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 S$214
includes taxes & fees
19 Oct - 20 Oct
Antica Pieve B&B
A rustic stone building with a courtyard.

17. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (57 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is S$155
includes taxes & fees
18 Oct - 19 Oct
Fullino Nero
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

18. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$97
includes taxes & fees
4 Nov - 5 Nov
Tuscasì Aparthotel
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

19. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is S$94
includes taxes & fees
15 Nov - 16 Nov
ApartHotel Anghel
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 Villa Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Absolutely amazing stay! The room was clean, large with a great view. The staff was always willing to help. Could not have asked for more. Highly recommend!"
Virginia 2-night trip
Posted 2 hours ago
La Certosa di Pontignano

Frequently asked questions

Can I find a holiday rental in Villa?

Yes, there are holiday rentals close to the most popular sights in Villa, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Villa speak positively about the beautiful countryside and charming coffee shops in this destination. While you're in the area, you can also enjoy the wineries and cathedral.

What are some of the best holiday rentals that Villa has to offer?

Borgo Argiano: This holiday home rental outside of Villa is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

What’s there to see and do in Villa?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. In the wider area, you’ll find Castello di Radda Winery and Castello di Albola.

What’s a holiday rental in Villa like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Villa. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.