Villa Vacation Rentals from $56: Search Short-Term Rentals

Q: 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 an espresso maker. You can relax into your vacation with a garden and a library.

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Our top choices for Villa vacation rentals

1. L' Eroico

Gaiole in Chianti

Angela

$151 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. Mariani Bed & Breakfast

Castellina in Chianti

Chie

$85 nightly

Aug 18 - Aug 19

Total with taxes and fees

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

3. Residenzia del Sogno

Castellina in Chianti

Katherine

$110 nightly

Aug 28 - Aug 29

Total with taxes and fees

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

4. Villa di Sotto

Castelnuovo Berardenga

Philippe

$160 nightly

Sep 10 - Sep 11

Total with taxes and fees

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

5. Borgo di Erboli

Cavriglia

$114 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Ruffoli

"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...

James

$186 nightly

Aug 17 - Aug 18

Total with taxes and fees

7. Riserva di Fizzano Residence

Castellina in Chianti

Janet

$165 nightly

Sep 8 - Sep 9

Total with taxes and fees

8. Chianti Village Morrocco

Barberino Tavarnelle

Chris

$96 nightly

Sep 15 - Sep 16

Total with taxes and fees

9. Borgo Argenina

Gaiole in Chianti

Sabatino

$235 nightly

Aug 23 - Aug 24

Total with taxes and fees

10. Villa San Filippo

Barberino Tavarnelle

Nadia

$109 nightly

Sep 12 - Sep 13

Total with taxes and fees

11. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

$134 nightly

Aug 31 - Sep 1

Total with taxes and fees

12. Villa Curina Resort

Castelnuovo Berardenga

Mary

$174 nightly

Aug 23 - Aug 24

Total with taxes and fees

13. Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

$303 nightly

Aug 19 - Aug 20

Total with taxes and fees

Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

14. Podere Vesta

Asciano

Katerine

$182 nightly

Aug 30 - Aug 31

Total with taxes and fees

Studio, Patio, Ground Floor | Terrace/patio

15. Fullino Nero

Siena

Christian

$92 nightly

Aug 23 - Aug 24

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, desk

16. Tuscasì Aparthotel

Sovicille

Sergey

$92 nightly

Aug 22 - Aug 23

Total with taxes and fees

17. Palazzo Pacini

Colle di Val d'Elsa

John

$113 nightly

Sep 2 - Sep 3

Total with taxes and fees

18. La Locanda di Pietracupa

Barberino Tavarnelle

Con

$175 nightly

Aug 21 - Aug 22

Total with taxes and fees

19. B&B Il Corso

Siena City Centre

Katherine

$117 nightly

Aug 23 - Aug 24

Total with taxes and fees

20. Villa with large garden in the Chianti hills

Siena

Julie H.

$160 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Villa Hotel Reviews

Villa Scacciapensieri Boutique Hotel

8/10 Good

"All in all a lovely property with lovely staff. Good location, easy bus ride to Siena town."

Villa Casagrande Resort & SPA

10/10 Excellent

"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

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 $56 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 wineries in this destination. While you're in the area, you can also enjoy the charming coffeehouses 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 an espresso maker. 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 Alta Val d'Elsa River 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.

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Check prices for these dates

Our top choices for Villa vacation rentals

1. L' Eroico

2. Mariani Bed & Breakfast

3. Residenzia del Sogno

4. Villa di Sotto

5. Borgo di Erboli

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

7. Riserva di Fizzano Residence

8. Chianti Village Morrocco

9. Borgo Argenina

10. Villa San Filippo

11. Casa Vacanze Squarcialupi

12. Villa Curina Resort

13. Terre di Baccio

14. Podere Vesta

15. Fullino Nero

16. Tuscasì Aparthotel

17. Palazzo Pacini

18. La Locanda di Pietracupa

19. B&B Il Corso

20. Villa with large garden in the Chianti hills

Find vacation rentals that suit your style

Top Villa Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Villa I Barronci Resort & Spa

Villa Casagrande Resort & SPA

Hotel Chiusarelli

Hotel Athena

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Find out more about Villa

Frequently asked questions

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