Default HTG hotel image

Villa Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Villa vacation rentals

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

1. 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 ￥19,932
￥22,629 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A stone building with a garden in front.

2. 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 ￥28,040
￥32,256 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Argenina
A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

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 ￥14,477
￥16,631 total
includes taxes & fees
Oct 31 - Nov 1
Mariani Bed & Breakfast
A stone building with a yellow sign reading "b&b erioico".

4. 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 ￥20,267
￥23,702 total
includes taxes & fees
Nov 5 - Nov 6
L' Eroico
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

5. 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 ￥20,794
￥23,577 total
includes taxes & fees
Nov 2 - Nov 3
Residenzia del Sogno
A villa with a swimming pool, outdoor seating, and a tennis court.

6. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (83 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is ￥20,739
￥23,519 total
includes taxes & fees
Oct 31 - Nov 1
Villa Curina Resort
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

7. 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 ￥18,104
￥20,974 total
includes taxes & fees
Nov 29 - Nov 30
Casa Vacanze Squarcialupi
A hot tub with two glasses of a beverage.

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is ￥29,334
￥32,267 total
includes taxes & fees
Oct 31 - Nov 1
Villa di Sotto
A table with breakfast items and a view of rolling hills.

9. 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 ￥11,325
￥12,811 total
includes taxes & fees
Nov 30 - Dec 1
Chianti Village Morrocco
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is ￥14,208
￥28,284 total
includes taxes & fees
Nov 2 - Nov 3
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
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.

11. 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 ￥42,734
￥47,713 total
includes taxes & fees
Oct 31 - Nov 1
Terre di Baccio
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

12. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (57 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ￥18,898
￥21,847 total
includes taxes & fees
Oct 31 - Nov 1
Villa San Filippo
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, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is ￥24,924
￥27,417 total
includes taxes & fees
Nov 2 - Nov 3
Relais Villa Belpoggio - Residenza d'Epoca
An arched entrance with a lantern above, flanked by two potted plants.

14. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is ￥25,175
￥28,398 total
includes taxes & fees
Nov 23 - Nov 24
Villa il Fedino
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

15. 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 ￥15,644
￥17,473 total
includes taxes & fees
Nov 1 - Nov 2
Relais Villa Belvedere
A rustic stone building with a courtyard.

16. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (59 reviews)
"Very nice place close to"
Canada
Annie
The price is ￥15,897
￥18,191 total
includes taxes & fees
Nov 2 - Nov 3
Fullino Nero
A modern hotel room with a bed, a built-in air conditioner, a small cabinet, and a door.

17. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥9,789
￥13,061 total
includes taxes & fees
Nov 20 - Nov 21
Tuscasì Aparthotel
A bedroom with a bed, bedside table, and a window with a view of greenery.

18. La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ￥15,061
￥17,273 total
includes taxes & fees
Nov 16 - Nov 17
La Coroncina Lodging
A two-story house with a patio area, potted plants, and outdoor furniture.

19. 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 ￥22,792
￥25,774 total
includes taxes & fees
Nov 12 - Nov 13
La Locanda di Pietracupa
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

20. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (93 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is ￥18,234
￥20,762 total
includes taxes & fees
Nov 3 - Nov 4
B&B La Fonte del Machiavelli
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Villa Hotel Reviews

Hotel Athena

Hotel Athena

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 19 hours ago
Hotel Athena

Find out more about Villa

Search for holiday rentals in Villa on Expedia! You can easily find your home rentals, villas, holiday apartments in Villa using one of the methods below:

  • View our selection of featured holiday rentals in Villa
  • Use the map to find apartments and other holiday homes in the Villa neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Villa while they last

Look no further and take a look at our great range of rental properties in Villa!

Frequently asked questions

Can I find a vacation rental in Villa?

Yes, there are vacation rentals near popular local attractions in Villa, or you can go with a secluded option if you're looking for a relaxing stay. Visitors to Villa speak positively about the beautiful countryside and charming coffeehouses in this destination. While you're in the area, you can also enjoy the wineries and cathedral.

What's the top vacation rental in Villa?

Borgo Argiano: This vacation home rental outside of Villa is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation 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 larger area, you’ll find Castello di Radda Winery and Castello di Albola.

What’s a vacation rental in Villa like?

Vacation rentals are private properties you can book for a couple of days or more in Villa. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.