
House holiday rentals in Montecastelli Pisano
Find and book unique houses on Airbnb
Top-rated house rentals in Montecastelli Pisano
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Montecastelli Pisano house rentals
House rentals with a pool

Family Forest - Pool in the Crete Senesi
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!

[Little Escape] 4 Beds + Private Panoramic Pool
We really enjoyed our stay at Tommaso's! The house is located in a lovely small village, very quiet and peaceful, surrounded by beautiful Tuscan nature. We even spotted a wild boar one early morning (so best to be cautious during early mornings and late nights). There’s a charming local restaurant just around the corner where we had a great dinner – Tommaso kindly helped us book a table for our first night, which was much appreciated. Nearest bigger shop is around 20-min drive. The house itself is spacious and well-equipped, we had everything we needed and more. Just a heads-up that the pool area is a short walk from the house (about 3 minutes), but so worth it. Communication with Tommaso was smooth and easy throughout. Thank you for a lovely stay!

Charming estate with views
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.

Podere Tignano, 4-bedroom villa in the Chianti!
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Casa di Lyndall - Entire house with exclusive pool
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

House Rigomagno Siena
We had a wonderful time in this absolutely cute house, which is surrounded by breathtaking nature. The tranquility is unique - you can only hear the chirping of the birds, and every now and then deer appear at the edge of the forest. Simply magical! The pool was well maintained and you had real peace. A real highlight for us was the kitchen: so lovingly furnished and exceptionally well equipped - we have never experienced anything like it! The gas stove and the high-quality oven have made cooking a pleasure. Host Diego was incredibly friendly, attentive and warm. You immediately feel welcome and well cared for. A perfect retreat for those who appreciate nature, tranquility and loving details.

Romantic cosy flat - Toscana Italy
This air B&B was in a beautiful area of Tuscany with breathtaking views. The property had many areas to sit and enjoy the rolling hills.

La Capanna: country house with magnificent view
Amazing place to stay, a great host and beautiful surroundings!
Weekly house rentals

Casa Ora d"Oro - Panoramic Views
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!

Cozy country house Podere Scorno with pool
Very local experience ~ It's great to be able to experience local life!It's like going back to the environment and house of my childhood. It's very comfortable!The host is also very nice!!!I gave a lot of recommendations!!!Thank you very much!!!

The charming cottage in Tuscany with breathtaking views
So Beautyful location and views. House is charming and clean. we recommend.

Captain's House | Monte Grosso, Elba
The fantastically beautiful Casa del Capitano has been renovated with great care and respect for the historic building, the environment and nature. The furnishings are luxurious (e.g. brick whirlpool made of natural stone) and really all conceivable amenities are available (e.g. ice cube machine). The view is incredible, 270 degrees of sea view is hard to comprehend. The hosts were always available, reliable, organized everything perfectly and accompanied us with advice and action (e.g. where to shop on Sundays after arrival by ferry) – from check-in to departure. The personal contact in particular was exceptionally warm and very pleasant. There were many small, loving details such as fresh lemons from the garden as well as herbs and "Elba fragrance" (Aqua dell'Elba) in the house. And the most detailed compilation of information about the house and the surrounding area that I have ever seen. You can feel that nothing has been spared here, so that the guests feel completely comfortable.

Countryhometuscany - House with Garden -
Beautiful property with warm, welcoming hosts. The bed was exceptionally comfortable, and everything is tastefully decorated The kitchen is fully equipped, perfect for cooking meals at home. The pool was a great temperature, immaculately clean, and came with stunning views of the surrounding countryside. The entire setting is peaceful and relaxing, yet only a 35-minute drive to Siena and 50 minutes to Florence. We especially loved watching the sunset at the nearby five-star Belmond hotel. We went for drinks at 7pm, enjoyed live music, and were surrounded by the heavenly scent of jasmine. There is no air conditioning but the fans were absolutely fine! Another highlight was La Speranza, a gorgeous deli serving excellent coffee, pastries, cheese, and wine. They kindly spoke English when we got stuck and made us feel so welcome.

a hideaway in the heart of tuscany
A perfect base to fully enjoy Radicondoli and Tuscany! Charming and peaceful place in the middle of the trees with a superb view of the valley!

La Casetta
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.

L'Uva Fragolina. House, Garden, Panoramic View
A Tuscan dream. Some days I had to pinch myself to realize that I wasn't in a movie. My girlfriend and I had a wonderful time in the region and also in the house. It was clean and tidy. The kitchen was unique and we also enjoyed grilling outside. We simply enjoyed it and felt at home. Finally, relaxation and tranquility, which you rarely experience. Thank you for your trust in this wonderful piece of Tuscany. A must-see for all those seeking peace and quiet or people who really want to experience what Tuscan flair means. We will be happy to come back!
Private house rentals

Montecatini Alto Art View
We loved staying in Carolina’s house in Montecatini Alto. It was a lovely welcoming place to wake up in and return to at the end of the day. The view from the windows and the patio is extraordinary and sitting out enjoying it was one of the best parts of the holiday. The house had all we needed. Carolina was a wonderful host; friendly, quick to reply and extremely helpful. The village is a lovely quiet place to stay and we wouldn’t look anywhere else if we return to the area.

Wonderful country house
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

Tuscan Villa with Privacy,Pool,near towncentre
We had a great time with our children at Antonio's! The entire property (including the pool) is super nice and very well maintained - so is the house in which we felt extremely comfortable. Antonio was always available and provided us with valuable tips about Volterra. We can fully recommend a stay and would be happy to come back.

Agriturismo Podere San Martino (apartment for two)
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!

La Bandita Dependance
We picked the location based on (very last minute) availability Airbnb’s. Both the city and Airbnb did not disappoint. The house was very chill and provided us with plenty of privacy and met all our needs. Azzurra was very helpful. And the city (with help of Azzuras tips) provided us with the relaxation we were looking for. Wish we booked a longer stay. Only recommendation for future guests, a car is required to navigate through the area.

La Cipressina Relax in Tuscany
This place was magical, if you are going to be in the area I highly recommend staying here. It’s just as beautiful as the pictures if not more so. Paola and Luigi were so friendly and kind. We are recommending this place to everyone we know.

Chianti House Stunning view 20 min. from Florence
Tommaso was very responsive and fantastic! Check in was a breeze. The pool was great. Overall, it was a great stay for our trip in Tuscany!

Private country house with garden, Wifi and A/C
It gave us exactly what we needed, a private and calm place to relax with a beautiful view, lots of space by the pool, around the garden, and if we wanted to be on our own, in our separate space. The hosts were really friendly and had great suggestions for places to go and always were responsive in case we needed anything, but they also gave us the space we needed – just what we were looking for. Thank you for a great time in Tuscany!
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Marina di Grosseto beach
- Kite Beach Fiumara
- Spiaggia di Capo Bianco
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Spiaggia Di Sansone
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Spiaggia Libera
- Cavallino Matto