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House vacation rentals in Montecastelli Pisano

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Popular amenities for Montecastelli Pisano house rentals

House rentals with a pool

Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.94 out of 5 average rating, 36 reviews

Family Forest - Pool in the Crete Senesi

JánRating, 5 stars1 week ago
The apartment really enchanted us, the rooms are nice, clean with air conditioning, stylish, in the living room a large TV, kitchen with everything that should be here. The "resort" itself was on a hill with beautiful views, a huge garden, a swimming pool, all stylish Tuscan, the surroundings are beautiful, peace, quiet, peace, everything you need here you will find. As the Italians say, it's "Tutto bene" here
Top guest favorite
A terrace overlooking the coastline is equipped with a large umbrella, sun loungers, and a small pool. The rocky coastline and clear blue water are visible, while lush greenery frames the outdoor area, creating a serene environment for relaxation.
Home in Rosignano Marittimo
4.95 out of 5 average rating, 79 reviews

Frontemare house with exclusive sea access

YusufRating, 5 stars1 week ago
Really very nice accommodation and a big thank you to Camilla who takes care of everything. For example, we can help you reserve a tennis court. Full recommendation!
Guest favorite
A private pool is set within a well-kept garden, surrounded by lush greenery and gently sloping grass. The octagonal pool is framed by stone pathways and features a small tree at its center. The tranquil outdoor space invites relaxation and enjoyment.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars2 weeks ago
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.
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Colle di Val d'Elsa
4.94 out of 5 average rating, 65 reviews

Countryhometuscany - House with Garden -

GabrielleRating, 5 stars2 weeks ago
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.
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
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 :)
Guest favorite
Home in Rigomagno
4.96 out of 5 average rating, 101 reviews

House Rigomagno Siena

LucyRating, 5 starstoday
A fantastic place to stay! Diego is extremely welcoming and gave us great recommendations and local info. The house and garden are even more beautiful than the photos - everything well-equipped, all that we needed. We had the perfect, peaceful week and look forward to coming back!
Guest favorite
A rectangular private pool is surrounded by a grassy area and olive trees, providing a serene outdoor setting. Six lounge chairs are placed neatly around the pool, offering space for relaxation. The sky is partly cloudy, enhancing the natural beauty of the surroundings.
Home in San Miniato
4.92 out of 5 average rating, 104 reviews

Lovely house in a scenic and paiceful location

BiancaRating, 5 stars1 week ago
We enjoyed Maria's great house. We were kindly welcomed by Maria and her family, where we were welcomed with a bottle of wine and delicious cake. We were with 6 adults. There's plenty of room. It's nice that every bedroom has its own bathroom. It is a beautiful house in a beautiful area with a wonderful swimming pool between the olive trees and it is really equipped with every comfort. Very nice is also the charger for the electric car. We picked up fresh bread every morning from the local baker in the village 5 minutes away by car. Good base for the beautiful cities such as Lucca, Siena, Florence. The beach is also great. We felt very much at home. Maria and family, thank you for the great time in your beautiful home.

Weekly house rentals

Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.93 out of 5 average rating, 42 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks ago
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!
Guest favorite
The image captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.94 out of 5 average rating, 78 reviews

Cozy country house Podere Scorno with pool

Rating, 5 stars1 week ago
Very local experience ~ It's also great to be able to experience local life!It's like going back to the environment and house when I was a kid. The stay was very comfortable!The host is also very nice!!!Gave a lot of recommendations!!!Thank you very much!!!
Top guest favorite
Home in Pontassieve
4.96 out of 5 average rating, 83 reviews

The charming cottage in Tuscany with breathtaking views

PoojaRating, 5 stars2 days ago
Stella is a beautiful person and a perfect host. Everything immediately felt like home. She explained everything very nicely. The location was serene and she gave a lot of information on things to do in that area. Would love to come again for sure.
Top guest favorite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 80 reviews

Captain's House | Monte Grosso, Elba

NataschaRating, 5 stars1 week ago
The fantastically beautiful Casa del Capitano has been renovated with great care and respect for the historic building, the environment and nature. The amenities are luxurious (e.g. brick whirlpool made of natural stone) and really all conceivable amenities are provided (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 assistance (e.g. where to shop on Sundays after arrival by ferry) – from check-in to departure. In particular, the personal contact was exceptionally warm and very likeable. 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 surroundings I've ever seen. You can feel that nothing has been spared here to make guests feel completely comfortable.
Top guest favorite
The bedroom features a spacious bed with a patterned bedspread. A wooden headboard adds warmth, complemented by two small bedside lamps. Large windows allow natural light to fill the space, with views of the surrounding landscape. Two paintings adorn the walls, enhancing the room's charm.
Home in Poggibonsi
4.92 out of 5 average rating, 59 reviews

Agriturismo Podere San Martino (apartment for two)

LukasRating, 5 stars1 month ago
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!
Superhost
A charming outdoor area features a wooden table surrounded by vibrant flowers in various pots. A shaded pergola provides a cozy atmosphere, while lush greenery decorates the rustic brick exterior of the structure. Soft sunlight enhances the inviting setting.
Home in Radicondoli
4.92 out of 5 average rating, 48 reviews

a hideaway in the heart of tuscany

ChiaraRating, 5 stars1 month ago
A perfect base to fully enjoy Radicondoli and Tuscany! Charming and peaceful place amongst the trees with superb views of the valley!
Superhost
A warm living area features arched windows allowing natural light to fill the space. A wooden coffee table is positioned in the center, surrounded by a comfortable sofa and a rattan chair. Shelving units display decorative items and a small plant sits atop the table.
Home in Lucignano
4.83 out of 5 average rating, 41 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.
Superhost
A private terrace features a wooden deck overlooking a panoramic view of the valley, with a steaming Jacuzzi positioned nearby. Sunlight filters through the trees, illuminating the area, while a cozy blanket and a few fruits are placed on the edge of the deck.
Home in Castelnuovo di Val di Cecina
4.93 out of 5 average rating, 68 reviews

L'Uva Fragolina. House, Garden, Panoramic View

DavidRating, 5 stars3 weeks ago
A Tuscan dream. Some days I had to pinch myself to understand that I was not in a movie. My girlfriend and I had a wonderful time in the area 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. For all those seeking peace or people who really want to experience what Tuscan flair means, a must-see. We will be happy to come back!

Private house rentals

Superhost
A tranquil swimming pool is surrounded by a well-maintained garden, reflecting the soft colors of the sunset. Lush greenery and vineyards are visible in the background, enhancing the serene atmosphere, while comfortable loungers are placed nearby for relaxation.
Home in Barberino Tavarnelle
4.77 out of 5 average rating, 56 reviews

7 min Cantina Antinori | Pool | Casa Sala & Pepe

NinaRating, 5 stars5 days ago
We spent a week in Silvio and Margherita's house with our two young children (5 and 6 years old). The hosts were always easily and quickly accessible and very helpful and friendly. The house is surrounded by vineyards and you have a fantastic view. There are some very good restaurants around that can be reached quickly by car. The garden is sweetly designed, but you share it with two other neighbors. However, you have your own garden section and pool to yourself. The house was clean, but very noisy (which did not bother us). A few pieces of furniture could be renewed (but did not restrict us and looks a bit authentic ;-) We would definitely come back.
Top guest favorite
An outdoor seating area features four wooden chairs arranged around a central table. The view highlights rolling hills and lush greenery, with mountains visible in the distance under a clear blue sky.
Home in Montecatini Alto
5 out of 5 average rating, 33 reviews

Montecatini Alto Art View

GarethRating, 5 stars6 days ago
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.
Guest favorite
A chlorine-free pool is set within a spacious garden, surrounded by lush greenery and trees. Sun loungers are placed nearby, and a charming stone house is visible in the background. The landscape offers expansive views of the Tuscan countryside under a bright blue sky.
Home in Volterra
4.88 out of 5 average rating, 51 reviews

Tuscan Villa with Privacy,Pool,near towncentre

SteffenRating, 5 stars1 week ago
We had a great time with our kids 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.
Guest favorite
A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars1 week ago
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.
Guest favorite
An outdoor seating area is surrounded by lush greenery and colorful flowers, featuring a decorative ladder against the wall. A sunny terrace showcases terracotta tiles, with expansive views of the rolling hills in the distance, framed by a partially open canopy.
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 71 reviews

Top rated.pool, Hot Tub, homeGym & private Garden

ClaudioRating, 5 stars1 week ago
Absolutely gorgeous property with country side view and a cozy outdoor area, plus two friendly black cats! Louise was the perfect host: friendly, generous, attentive, she even offered to help us out when we had a setback that was totally unrelated to our stay at her property. Highly recommend to any traveller seeking an idyllic stay in the Tuscan countryside!
Top guest favorite
A private pool is surrounded by lush greenery and flowering shrubs, inviting relaxation. Lounge chairs are positioned nearby under the shade of trees, creating a serene outdoor space. The pool area is accessible, providing a peaceful retreat for guests.
Home in San Gimignano
4.98 out of 5 average rating, 41 reviews

Tuscany:Stone house, private pool and garden

MarceloRating, 5 stars1 week ago
This house is the perfect place for two families traveling together. It’s incredibly cozy, thoughtfully designed, and fully equipped with amenities that let you truly enjoy the beauty of the Tuscan countryside. From the moment we arrived, we felt at home. The hosts went above and beyond — welcoming us with fresh fruit, traditional sweets, bottled water, coffee, milk, and a selection of Tuscan wines, which we truly appreciated. They also provided high-quality Italian hygiene products, which added a thoughtful and luxurious touch to our stay. One of the highlights for us was the host’s responsiveness. Communication was always fast, helpful, and friendly — a detail that made a big difference. We didn’t get a chance to use the private pool due to our tight schedule, but the property still gave us a real sense of independence, comfort, and safety. I 100% recommend this property. It’s a peaceful, beautiful place — perfect for relaxing, connecting with nature, and creating memories
Top guest favorite
A private swimming pool is framed by a sun terrace furnished with several white loungers. A shaded seating area provides a relaxing spot nearby, surrounded by lush greenery and trees. Natural stone steps lead along the edge of the space, enhancing the tranquil outdoor setting.
Home in Montevarchi
5 out of 5 average rating, 25 reviews

Casa San Ripa: Relax Oasis with Private Pool

CarolinaRating, 5 stars6 days ago
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!
Guest favorite
A logo featuring a house with a welcoming doorway, adorned with potted plants on either side. The design includes the text 'DEPENDANCE LA BANDITA' and 'ESTD 2023,' framed by delicate floral elements, suggesting a curated and inviting space.
Home in Marina di Castagneto Carducci
4.98 out of 5 average rating, 60 reviews

La Bandita Dependance

AlexanderRating, 5 stars2 days ago
A cozy paradise nestled among an idyllic olive orchard, ran by the host family who gave us a sample bottle of their olive oil to enjoy during our stay (delicious!). Azzurra was very proactive, flexible and helpful during check in, and even gave us fabulous recommendations for local restaurants, nearby beaches and more. Beyond that, the apartment itself was full of little niceties and thoughtful details that showed Azzurra truly knows how to properly host guests who may be weary from travels. Lastly, we made friends with a charming and well-behaved old dog who politely greeted us during our morning coffee on the patio. 10/10, would love to return!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Pisa
  5. Montecastelli Pisano
  6. House rentals