Holiday Rentals in Villastrada

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Our top choices for Villastrada holiday rentals

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is €199
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is €71
includes taxes & fees
17 Dec - 18 Dec
Abbadia Sicille Relais

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
chiusi
10.0 out of 10, Exceptional, (57)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is €98
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is €91
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza Fabroni

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is €252
includes taxes & fees
17 Dec - 18 Dec
Il Tosco

Country House With Private Pool

Country House With Private Pool
Toscane
10.0 out of 10, Exceptional, (13)
"We had such a lovely week staying in this farmhouse just outside Citta della Pieve. The house itself and interiors are beautiful - the kitchen is well equipped, the beds are incredibly comfortable, the bathrooms modern, the pool is an excellent size, and the views are amazing. The hosts were incredibly friendly and generous, and really added to our overall experience. I would highly recommend a stay here - you will not be disappointed!"
United Kingdom
Clare C.
Country House With Private Pool

Villa Casale Silvia Large Private Pool, A/C, WiFi

Villa Casale Silvia Large Private Pool, A/C, WiFi
Parrano
9.4 out of 10, Exceptional, (22)
"A lovely escape - we enjoyed every moment!"
United States
Anonymous traveller
Villa Casale Silvia Large Private Pool, A/C, WiFi

Luxury Cortona view hilltop Villa

Luxury Cortona view hilltop Villa
cortona
10.0 out of 10, Exceptional, (50)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Australia
Belinda P.
Luxury Cortona view hilltop Villa

House with garden and panoramic view over Lake Trasimeno

House with garden and panoramic view over Lake Trasimeno
Tuoro Sul Trasimeno
9.8 out of 10, Exceptional, (47)
"We had a very pleasant stay and enjoyed the house and surroundings to the fullest. The view of the lake is breathtaking.We had very good communication with the owner and bought some of his very good wines."
Denmark
Lars B.
House with garden and panoramic view over Lake Trasimeno

Osteria del Borgo

Osteria del Borgo
Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo

Villa Piandisette - Four Bedroom Villa, Sleeps 10

Villa Piandisette - Four Bedroom Villa, Sleeps 10
Cetona
9.4 out of 10, Exceptional, (11)
"Very nice property, clean and chic, all the furniture and amenities you need. Very big and specious. In summer can be very hot but the villa has Airconditioning in every room. Owner very nice and helpful, we communicated via WhatsUp for everything. The closest supermarket is 10 min drive away so plan your shopping well. "
Austria
Ana J.
Villa Piandisette - Four Bedroom Villa, Sleeps 10

Casina in authentic Tuscany

Casina in authentic Tuscany
Cortona
9.8 out of 10, Exceptional, (69)
"This was a perfect stay. Picturesque location, close to Cortona and wineries and shops- we even walked to one of them. Best of all though was the kindness of the host who left us wine, salad, bruschette and cantucci. We would LOVE to come back one day! "
Australia
Catherine G.
Casina in authentic Tuscany

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

Villa with swimming pool and garden- San Feliciano, Trasimeno lake
San Feliciano
8.4 out of 10, Very good, (46)
"We had a great Family Holiday there. We enjoyed the pool so much and the nice terrasse, where we had all our meals and sat in the evenings to watch the Sunset on the lake. We liked the dogs visiting us and Massimo was always helpful."
Germany
Karin
Villa with swimming pool and garden- San Feliciano, Trasimeno lake

Heritage Tuscan Farmhouse with private swimming pool

Heritage Tuscan Farmhouse with private swimming pool
Cortona
10.0 out of 10, Exceptional, (48)
"Beautiful location. Great base to visit Cortona, Montepulciano, Siena, and Florence. Louise was wonderful and helpful. Thoroughly enjoyed our stay. "
United States
Clyde H.
Heritage Tuscan Farmhouse with private swimming pool

Villa with private pool, air conditioning near wineries at 3km from village

Villa with private pool, air conditioning near wineries at 3km from village
CHIANCIANO terme
9.4 out of 10, Exceptional, (46)
"It was amazing!! Great space for 7 adults. Pool area is great. Definitely do a meal with Leonardo. "
United States
Carol W.
Villa with private pool, air conditioning near wineries at 3km from village

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Montepulciano
9.6 out of 10, Exceptional, (82)
"This house and location was perfect. Beautiful views and a great kitchen. Montepulciano was our favorite town that we visited on our trip. Easy check in and the host had a document that she sent us that had a lot of great info."
United States
Tom K.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie
Montepulciano
9.6 out of 10, Exceptional, (4)
"My two friends and I enjoyed our stay at San Bono. The highlight was having the family make and serve us an authentic Tuscan meal! The view is amazing and the location was perfect!"
United States
Flourish Flowers
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (7)
"excellent stay. Beautiful pool, well equipped kitchen, very friendly host.Perfect for the visit of the surrondigns: Perugia, the lake, Montepulciano."
United States
cinzia c.
The price is €173
includes taxes & fees
17 Dec - 18 Dec
Villa Graziella, Romantic Perugia

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Castiglione d'Orcia
9.8 out of 10, Exceptional, (12)
"This lovely, sprawling farm house in the Val d’Orcia has plenty of space for a large family gathering, with six bedrooms, a gorgeous barbecue and swimming pool. Excellent spot from which to explore hill towns, visit wineries, and eat some excellent Tuscan cuisine. Don’t miss the hot springs at Bagni San Filippo! "
United States
Andrew P.
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
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 Villastrada Hotel Reviews

Find out more about Villastrada

Everything you need to know about Villastrada holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Villastrada holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Villastrada holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Villastrada holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Villastrada. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Villastrada holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Villastrada holiday rentals we have selected for you start as low as €71 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Villastrada rentals

At Expedia, we put the best Villastrada holiday 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 Villastrada 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 Villastrada holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Villastrada. 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 holiday rentals in Villastrada?

Yes, there are holiday rentals close to the most popular sights in Villastrada, or you can select a more secluded option if you're looking for a relaxing stay.

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

Villa with swimming pool and garden- San Feliciano, Trasimeno lake: This holiday home rental outside of Villastrada is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a pool table and 1 hot tub.

What’s there to see and do in Villastrada?

Explore the area and family-friendly sights such as Centro Servizi Turistici Citta della Pieve, or get out into nature at a spot like Lake Trasimeno. In the wider area, you’ll find Labyrinth of Porsenna and Rocca del Leone.

What’s a holiday rental in Villastrada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Villastrada. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a small group gathering.