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Villa Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Villa vacation 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
$142 nightly
The price is $165
Oct 9 - Oct 10
Total with taxes and fees
L' Eroico
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

2. 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
$81 nightly
The price is $94
Oct 15 - Oct 16
Total with taxes and fees
Mariani Bed & Breakfast
A pool area with a water slide and a stage for performances.

3. Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (24 reviews)
"It was clean and safe."
United Kingdom
Laka
$68 nightly
The price is $77
Oct 1 - Oct 2
Total with taxes and fees
Villa Norcenni Aparthotel
A table with breakfast items and a view of rolling hills.

4. 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
$73 nightly
The price is $82
Oct 13 - Oct 14
Total with taxes and fees
Chianti Village Morrocco
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
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
$127 nightly
The price is $145
Oct 6 - Oct 7
Total with taxes and fees
Residenzia del Sogno
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

6. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (56 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
$124 nightly
The price is $141
Oct 7 - Oct 8
Total with taxes and fees
Villa Rosa Panzano
A stone building with a garden in front.

7. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
$238 nightly
The price is $271
Oct 1 - Oct 2
Total with taxes and fees
Borgo Argenina
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$206 nightly
The price is $226
Oct 1 - Oct 2
Total with taxes and fees
Villa di Sotto
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

9. 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, (25 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
$182 nightly
The price is $182
Oct 1 - Oct 2
Total with taxes and fees
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A villa with a swimming pool, outdoor seating, and a tennis court.

10. 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
$139 nightly
The price is $158
Oct 4 - Oct 5
Total with taxes and fees
Villa Curina Resort
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

11. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 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
$130 nightly
The price is $145
Oct 20 - Oct 21
Total with taxes and fees
Casa Vacanze Squarcialupi
A rustic stone building with a courtyard.

12. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$108 nightly
The price is $123
Oct 5 - Oct 6
Total with taxes and fees
Fullino Nero
A pool area with a water slide and a stage for performances.

13. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (333 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
$63 nightly
The price is $71
Oct 1 - Oct 2
Total with taxes and fees
Hu Norcenni Girasole Village
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

14. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$167 nightly
The price is $186
Oct 8 - Oct 9
Total with taxes and fees
Riserva di Fizzano Residence
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

15. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (53 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$89 nightly
The price is $104
Oct 31 - Nov 1
Total with taxes and fees
Villa San Filippo
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

16. 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
$152 nightly
The price is $168
Oct 5 - Oct 6
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
$67 nightly
The price is $78
Oct 27 - Oct 28
Total with taxes and fees
Domus il Palio B&B
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, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$78 nightly
The price is $89
Oct 31 - Nov 1
Total with taxes and fees
Tuscasì Aparthotel
A dining area with a table set for two, featuring a view of greenery through a window.

19. 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
$158 nightly
The price is $178
Oct 6 - Oct 7
Total with taxes and fees
La Locanda di Pietracupa
A market with a sign reading "BAR IL POGGETTO MARKET".

20. Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (79 reviews)
"Nice property, very reasonable price"
United States
Alex
$54 nightly
The price is $63
Oct 30 - Oct 31
Total with taxes and fees
Camping Village Il Poggetto.
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
"good to stay"
Jinhee 1-night trip
Posted 20 hours ago
La Certosa di Pontignano

Find out more about Villa

Everything you need to know about Villa 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 Villa 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.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Villa vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Villa vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Villa. 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 Villa 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 $48 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Villa rentals

At Expedia, we put the best Villa vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Villa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Villa vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Villa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.