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Villa vacation rentals in Montespertoli

Find and book unique villas on Airbnb

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Popular amenities for Montespertoli villa rentals

Private villa rentals

Guest favorite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars1 week ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top guest favorite
Villa in Lucca
4.97 out of 5 average rating, 78 reviews

Villa Barsocchini intera

LozyRating, 5 stars4 days ago
Thankyou Brian (and family) for what was an unforgettable magical experience. The villa far surpassed all our expectations. The villa is beyond beautiful and oozes rustic charm, perfect for a large group. Rooms were clean and with beautiful views (on the top floor) to wake up to, so much so that it felt like a dream. Bathrooms were lovely and higher spec than expected for such an old building. swimming pool serves it's purpose, but it's in a gorgeous garden amongst olive groves....stunning. Brian and family were the perfect balance of keeping in touch and ensuring we had everything we needed whilst ensuring that we felt we had the place to ourselves, a perfectly ran operation. We arranged a dinner one evening in the house cooked by Brian's mother which was an amazing experience to enjoy such a wonderful setting with friends. thank you Brian! we already hope to return in future.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 26 reviews

Luxury Tuscany Villa on the hill with private pool

SandraRating, 5 stars5 days ago
We were very satisfied with our vacation home from Stefania. Great, spacious, secluded garden with lots of olive trees. Pergola with seating area invites you to linger. The cleanliness of the place was also extremely good. The beds or mattresses were very comfortable and the bedrooms nicely furnished. Stefania provided us with many tips and recommendations. She also booked a table for us twice at the nearby Osteria di Valgiano. Great food at a low price with a great view of Lucca. Stefania responded quickly and kindly to questions. We would have liked to have stayed longer and will definitely come back!
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 19 reviews

Exclusive Farmhouse Pool & View of San Gimignano

AlineRating, 5 stars1 month ago
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!
Superhost
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 People - Private Pool

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.
Top guest favorite
Villa in Bucine
4.98 out of 5 average rating, 43 reviews

Villa Tontenano Capannole Chianti private pool 12

IndunRating, 5 stars3 weeks ago
This place is fabulous. Margherita was responsive so quickly. We had a 11 people six adults and five kids. Loved the pool and hot tub. Margherita made reservations for us and suggested day trips. She even got a wheelchair for me for the Hill towns. Take advantage of their cooking. they did meals for us, which were fantastic. And even organized a birthday dinner for the three young girls. They did the birthday cake and even gave them a gift. It was fabulous. Don’t hesitate to book. We did day trips to Sienna, pisa,Luca, panzano, pienza and multipulciano. And two trips to the luxury mall.!Her parents are so helpful too. Olive oil and their wine is fantastic. The only regret I have is that we didn’t have extra days and spend the time right around villa. I think we would have really enjoyed the wine tasting and olive tastings. I would’ve stayed easily another week. Do take advantage of her massages too. My kids thoroughly enjoyed our visit. It exceeded my expectations!!!!! Ten stars!!!!!!
Top guest favorite
Villa in Greve in Chianti
5 out of 5 average rating, 47 reviews

Villa Corte - Casine al Sole (Villa Court - Casine al Sole)

EniRating, 5 stars1 month ago
Wonderful villa in Greve, perfect for our large group. Everyone had their own bed and bath and the house was spotless when we checked in. Federico was always willing to answer questions about the house as well as local recommendations and even made us a few reservations. Would 100% stay here again when in Tuscany.
Top guest favorite
Villa in Barberino Tavarnelle
4.97 out of 5 average rating, 89 reviews

CasaDiManuela:TotallyPrivateChiantiVilla withTub

DonaldRating, 5 stars1 week ago
Giada's home in Tuscany is beautiful. Great outdoor space, spacious and with amazing views of the Tuscan surroundings. It's convenient to local sites and only about an hour away from Florence by train; it's a relatively short drive to Siena. The house is well equipped with a fully functional kitchen, and (most importantly) a Nespresso coffee machine! There were 4 of us and we were quite comfortable in the three bedrooms. Highly recommended. It was a perfect stay.

Luxury villa rentals

Top guest favorite
Villa in Poppi
5 out of 5 average rating, 15 reviews

Villa Lux Poggelleri with a unique view of the Casentino

KasperRating, 5 stars3 weeks ago
We are a family of 5 who had a fantastic stay. The house is huge and very nice and the view is unbeatable. All stress leaves the body when you are there. Everywhere you looked, there were exceptionally beautiful views. In addition, Lucia and Frederico were so warm people and made us feel very welcome. We will definitely be back!
Superhost
Villa in Greve in Chianti
4.85 out of 5 average rating, 34 reviews

Romantic Villa with private pool and fabulous view

AllisonRating, 5 stars6 days ago
The views from Janine’s villa are breathtaking and pictures don’t do it justice. It was so quiet and peaceful, a little slice of heaven. We visited with our two boys (5 and 10) who loved the pool and the spaciousness of the home and the grounds. Being so close to Panzano was the best perk because we were within a 7 minute drive to town for great restaurants, simple groceries, and pastries (as opposed to other villas that require a longer drive to get anywhere to eat/visit). A great base for exploring the surrounding area as well, and an easy day trip to Florence. There are excellent wineries within a 3 minute drive! Janine was a lovely, kind, and helpful host and gave us tips for local restaurants as well as places for our trip to Florence. It was very hot during our stay but the fans were enough to keep cool at night and we didn’t turn on the A/C. We stumbled across this little gem and if you’re lucky enough to do so as well, you will be swept up by the magic of the views and villa.
Superhost
Villa in Galluzzo
4.73 out of 5 average rating, 11 reviews

Tenuta del Podestà villa di charme in Firenze

BrianRating, 5 stars8 months ago
David’s place embodies elegance and tranquility. Beautiful interior with intricate touches. The backyard was huge and our pup enjoyed running around on it. It’s as described in the pictures. David was also a very kind host. Responsive to our questions and insightful when it came down to recommendations. Highly recommend to anyone considering booking!
Guest favorite
Villa in Buti
4.96 out of 5 average rating, 46 reviews

Villa sii felice

KristinRating, 5 stars1 week ago
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!
Top guest favorite
Villa in Florence
5 out of 5 average rating, 8 reviews

Florence best view villa Fiaccherella

DimitriosRating, 5 stars3 weeks ago
We booked the place for myself and my wife, my 2 daughters with thei husbands and my 4 grandchildren (aged 2 to 13) and their nunny. We all enjoyed our stay, we all felt we had privacy when we needed, and common areas to be all together. Excellent place for large families or parties. The host ready to answer all questions.
Superhost
Villa in Camaiore
4.93 out of 5 average rating, 45 reviews

La Dolce Vita - Tuscan experience

JonathanRating, 5 stars2 weeks ago
We had a wonderful stay, the house really felt like a home and was instantly relaxing. The whole booking and check in process was very straightforward and Giuseppe who met us to show us around the property and hand over the keys was very welcoming, kind and informative. The house has wonderfully peaceful location, with beautiful views. It has been furnished with excellent taste, and so adds to the feeling of being in a real home rather than a rental. The gardens and pool are delightful and evenings on the loggia will be remembered for a long time, we cant wait to return!
Guest favorite
Villa in Tignano
4.95 out of 5 average rating, 174 reviews

Villa Isabella

AndrewRating, 5 stars3 days ago
Wow! Christina’s property is beautiful! The surrounding Tuscan hills make for a breathtaking setting, with wonderful views to the east and west for sunrise and sunset. We enjoyed drinking in the views from the terraces and while cooling off in the pool, which was a great size and bigger than we had imagined from the pictures. Watching the local swallows, who would soar overhead and drink from the pool, was a real treat. The villa itself was spacious, clean and thoughtfully decorated. Christina was a wonderful host, ready to greet us on arrival and to help us check-out, and responsive to all our messages. She even bought us a lilo for the pool when I asked if there was one! Christina had lots of suggestions of local things to do, from the best artisanal butcher from whom to purchase bistecca alla fiorentina, to where to buy the finest locally produced olive oil and Chianti. We hope to return, a real treat! Grazie mille, Christina!
Top guest favorite
Villa in Gaiole in Chianti
4.98 out of 5 average rating, 49 reviews

Sestuccia

AnnieRating, 5 stars1 month ago
This was the most magical place so spend a week in Chianti! The villa is exceptionally beautiful, and has everything you could need for a comfortable stay. The grounds were spectacular, with many things to do and different areas to sit and enjoy. My toddler especially loved picking strawberries from the small garden and collecting eggs from the chickens for breakfast. The hosts were lovely and helpful with any questions we had, and took great care of us. The town of Gaiole in Chianti is very close and with great restaurants and things to do. A perfect spot I can’t recommend highly enough!

Villa rentals with a pool

Guest favorite
Villa in Peccioli
4.92 out of 5 average rating, 12 reviews

Luxury villa with Pool, games room & Bocce court

KathleenRating, 5 stars8 months ago
My family and I -- six adults and a 9 month old -- spent two delightful weeks at Il Granaio. Before our arrival, Greg (the host) put me in touch with Ally, the property manager, who provided much useful information in advance and ensured we could find our way to the hidden gem that is Il Granaio. Once we arrived, Ally was available as needed, responsive to my queries as we settled in. We enjoyed the Villa and property immensely, using it as a base camp as we did day trips all around Tuscany and a longer visit to the Ligurian coast. The house was comfortable, attractive, and well-outfitted, with fantastic views from the second floor; the surrounding countryside was peaceful and beautiful; the pool was a perfect place to cool off and relax after being out and about; and the billiard table provided enjoyment for all! And having our own washer and dryer was incredibly convenient, especially when traveling with a baby. Wonderful memories were made for our family at Il Granaio!
Top guest favorite
Villa in Barberino Tavarnelle
5 out of 5 average rating, 37 reviews

Valluccia 51

LeeRating, 5 stars3 weeks ago
Thank you Tommaso, a fantastic view and pool, a wonderful villa and you’re proactive assistance at every turn, highly recommended. The drive down the track is worthwhile for the tranquility it affords. Can’t recommend Tommy & the villa enough & as for Tuscany, it’s incredible!
Top guest favorite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 52 reviews

The Lazy Oak

KathleenRating, 5 stars1 day ago
We (2 couples) had a wonderful time at the Lazy Oak Villa. The booklet in the house had great recommendations for dinner in Loro Ciuffenna. We did wine tastings at 2 family vineyards located very close to the villa- Morandi Organic Winery with Denis and Società Agricola Caspriano with Simona. Highly recommend both. One of our couples was celebrating an anniversary and Mario arranged for a chef to come to the villa and prepare a traditional Tuscan meal. It was beyond words! The pool was pristine and such a great bonus with the summer heat.
Top guest favorite
Villa in Volterra
5 out of 5 average rating, 24 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars1 month ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Top guest favorite
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars3 weeks ago
We had an amazing stay at the villa. A modern house in quiet surroundings with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Top guest favorite
Villa in Lucca
4.98 out of 5 average rating, 80 reviews

Villa Marì

SamuelRating, 5 stars2 weeks ago
We had an absolutely wonderful stay at this beautiful villa in Lucca! The property is stunning, with breathtaking views of the surrounding countryside that made every morning feel like a dream. The villa itself is spacious, clean, and tastefully decorated, striking the perfect balance between rustic charm and modern comfort. Our hosts were incredibly welcoming and attentive—they went above and beyond to make sure we had everything we needed and offered great tips for local spots to explore. It was clear they truly cared about creating a memorable experience for their guests. Most of all, the peaceful atmosphere made it the perfect place to relax and unwind. Whether enjoying a glass of wine on the terrace or simply soaking in the scenery, it was exactly the getaway we were hoping for. We can’t wait to come back!
Superhost
Villa in Greve in Chianti
4.89 out of 5 average rating, 85 reviews

Put down your luggage, this is just the beggining!

CliveRating, 5 stars9 months ago
The villa is situated on the outskirts of Greve in Chianti. For us it was a perfect location - enjoy country views yet walkable to the town centre for restaurants and shops. Four double rooms, each with an ensuite/shower. Everything you need for a great time - swimming pool, terrace with built in BBQ. Kitchen is well equipped with dishwasher, large fridge freezer and large range cooker. Kitchen table was ideal as we could all fit round and it made the kitchen the social hub as we used the comfy lounge for those quieter moments. Definitely recommend. We would be happy to go back.
Top guest favorite
Villa in Siena
5 out of 5 average rating, 13 reviews

L’Apparita del Peruzzi, pool, super view, save30% 7d +

AlexanderRating, 5 stars1 week ago
An enchanting place. The villa is steeped in history and the gardens with a small amphitheater and a distant view of Siena are spectacular. Great location from which to explore the rest of Tuscany. My family and I have enjoyed our stay.

Destinations to explore