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House vacation rentals in Roccastrada

Find and book unique houses on Airbnb

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Popular amenities for Roccastrada house rentals

House rentals with a pool

Guest favorite
A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.
Home in San Miniato
4.92 out of 5 average rating, 133 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars2 weeks ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
Guest favorite
An outdoor swimming pool is surrounded by green grass and features a clear blue water surface. Sun loungers are positioned nearby, while a panoramic view of hills and distant landscape can be seen in the background. The area is well-lit and inviting.
Home in Catabbio
4.89 out of 5 average rating, 159 reviews

Country house La Meria

AlexRating, 5 stars1 month ago
If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!
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, 137 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars6 days 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 :)
Superhost
A stone pathway leads to a charming rustic building, surrounded by greenery and blooming flowers. To the side, a flat stone table under a large tree provides a serene outdoor space, inviting relaxation amidst nature.
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars4 weeks ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!
Guest favorite
Home in Rigomagno
4.96 out of 5 average rating, 100 reviews

House Rigomagno Siena

Marco JustusRating, 5 stars1 week ago
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 decorated and exceptionally well equipped – we have never experienced this before! The gas stove and the high-quality oven 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.
Superhost
An underground heated pool is surrounded by rustic brick walls, featuring soothing green water and a gentle current. The ceiling has exposed brick, creating an inviting, natural atmosphere. The space offers privacy, ideal for relaxation and rejuvenation.
Home in Rifredi
4.83 out of 5 average rating, 113 reviews

Country House w/ heated Pool near the City Centre

SandraRating, 5 stars2 months ago
We thoroughly enjoyed our stay at this wonderful place. The quiet surroundings were perfect for a break from the hustle and bustle of Florence. And it's still easily accessible by tram. Giacomo was a wonderful host and was always available. We truly enjoyed every day there.
Superhost
Home in Anghiari
4.88 out of 5 average rating, 140 reviews

Tuscan dream in the ancient Tobacco's villa, sauna

JacquelineRating, 5 stars1 month ago
The house is beautiful and unlike anything else. What made the experience amazing was one of the hosts, Daniela. Daniela greeted us upon check in, walked us around the house and went above and beyond and booked us a wine tour where he graciously translated everything in English during the entire experience. Daniela made the place feel like home and I couldn’t recommend him and the experience he provides more.
Guest favorite
An open natural swimming pool is surrounded by lush greenery, featuring wooden lounge chairs positioned along the poolside. The tranquil water reflects the surrounding landscape, while a gentle waterfall can be seen emerging from one end, enhancing the serene environment.
Home in Certaldo
4.91 out of 5 average rating, 130 reviews

Paluffo Stillo House

LeahRating, 5 stars2 weeks ago
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!

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
4.98 out of 5 average rating, 40 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 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
4.97 out of 5 average rating, 34 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars1 week ago
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!
Top guest favorite
A warm guest room features a spacious bed adorned with a patterned coverlet. Two bedside lamps illuminate the area, beside a wooden chair and a small dresser. A large painting hangs on the wall, while a window offers natural light, showcasing rustic decor elements.
Home in Chiusdino
5 out of 5 average rating, 27 reviews

Il Camino: cosy & artfully inspired country house

MildredRating, 5 stars1 month ago
Thomas was so sweet and helpful. He was an absolute gentleman and wonderful host. The views were amazing. Very homey and decorated in the Tuscany style. Close to town but perfect for a quiet escape in the Tuscan countryside.
Top guest favorite
A rustic kitchen area is nestled against a stone wall, featuring a wooden bar table with two round stools. Minimalistic shelves hold kitchen essentials, while light streams through a window, illuminating the space and connecting it with the adjoining sleeping area.
Home in Montemassi
4.96 out of 5 average rating, 49 reviews

Capezzuolo 33

BenRating, 5 stars1 week ago
This apartment was so beautiful and the views were even better. We had an amazing stay here as our base for exploring Tuscany - visiting the Val d’Orcia and the thermal baths were a highlight! Lucia and Marco met us on arrival and were extremely friendly and gave us plenty of advice and places to visit. There was an issue with the boiler but Lucia was straight on it and it was fixed by the time we were home for the day. Thank you so much!
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 stars2 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!
Guest favorite
The exterior of the stone villa features a shaded pergola surrounded by landscaped grounds. A gravel pathway leads to several chairs arranged invitingly under the structure. Lush greenery and trees add to the tranquil outdoor atmosphere, complemented by a clear sky with scattered clouds.
Home in Gavorrano
5 out of 5 average rating, 11 reviews

House in the Maremma hills

JessicaRating, 5 stars3 weeks ago
A stunning property in the Tuscan hills, with the small village of Ribolla nearby with local amenities. Friendly welcoming hosts, set on a winery. Facilities second to none, absolutely gorgeous swimming pool and view across the value. Will definitely be returning. Take your iPad if you need to watch any tv! Bellissimo!
Guest favorite
A charming exterior view of a white house surrounded by lush greenery. Bright pink flowers are prominently displayed in the foreground. A shaded outdoor dining area features a table and two chairs, positioned near trees against a clear blue sky.
Home in Castiglione della Pescaia
4.92 out of 5 average rating, 13 reviews

Casetta Rosa: relaxation between sea and nature

StefaniaRating, 5 stars6 days ago
We were guests with our 5 dogs for which we had a part of the garden for exclusive use, fenced. Ideal for those who want accommodation outside the city center but within a 5-minute drive. The first beach is also 5 minutes away, so it's very convenient! Raffaele and his mother Rosa were very kind!!! Recommended place to stay!
Top guest favorite
A rustic stone building features a wooden balcony with a lantern overhead, reflecting traditional architecture. Red roses bloom at the base, adding color to the scene, while wooden shutters frame the windows above, harmonizing with the natural surroundings.
Home in Castello di Tocchi
4.97 out of 5 average rating, 61 reviews

Apartment in the village of Castello di Tocchi

MartaRating, 5 stars1 month ago
My boyfriend and I had a great time, a really quiet place, there was a lot of peace. Luciana and her husband Piero welcomed us as if we were at home and were very kind and available. We moved by car to reach the various places we were interested in, but we always returned with pleasure "at home".

Private house rentals

Top guest favorite
The living area features exposed stone walls and wooden beams, creating a rustic ambiance. A spacious sectional sofa is complemented by a round accent chair. A round mirror reflects light from the window, while a decorative fireplace adds warmth to the space.
Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
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, 77 reviews

Cozy country house Podere Scorno with pool

PaoloRating, 5 stars1 week ago
Staying with Virginia and her family was a wonderful experience that I will carry in my heart. The accommodation is immersed in the beautiful Sienese countryside. The house is cared for in every detail, very clean, cozy and equipped with everything you need to feel at home, with that rustic and authentic touch that makes the atmosphere truly special. Kind, helpful, and always ready to offer advice on places to visit, typical restaurants, and activities in the surrounding area. The silence and tranquility of the place allow you to relax completely, but at the same time the location is strategic for visiting Siena, the Val d'Orcia and many other enchanting villages of Tuscany. Highly recommended for those looking for an authentic stay, in contact with nature and true Tuscan hospitality.
Top guest favorite
Home in Montalcino
5 out of 5 average rating, 8 reviews

New Palazzo in City Center: 4 King Bedrms 6 Bath

RiteshRating, 5 stars1 month ago
Thank you Brian for sharing your beautiful home with us for a couple of days. Your home is by far the best maintained and most well equipped and pristine places that we have stayed so far. We had the most amazing time in the house as well as walking around the city in the evenings. The location is perfect for everything from shopping to restaurants and wine tastings. Thank you Valentina for taking care of our needs during the stay, we would definitely return to stay at your house the next time when we visit. Thank you so much🙏
Top guest favorite
Home in Pereta
5 out of 5 average rating, 56 reviews

Bel Casale with sea view and the mediaeval village

AmarRating, 5 stars1 week ago
Staying at Paola and Nino’s place was one of the highlights of our trip. The house is even more beautiful than the photos, with every detail thoughtfully considered and a setting that truly captures the essence of Tuscan magic. It’s incredibly peaceful, with sweeping views and a real sense of privacy, yet close enough to explore charming villages and beaches. The house is well-equipped and very comfortable, with excellent air conditioning in the bedrooms, a real plus during the summer heat. Paola and Nino were the most gracious hosts, warm, welcoming, and always available if we needed anything, yet also giving us plenty of space. Their three sweet labradors were a lovely bonus! We truly didn’t want to leave and would return in a heartbeat.
Guest favorite
An exclusive terrace features two cushioned chairs facing a small table, set with two glasses and a plate of snacks. The view spans rolling countryside and distant hills, with soft twilight colors enhancing the serene atmosphere of the outdoor space.
Home in Montalcino
4.94 out of 5 average rating, 33 reviews

Domus Antiqua

KellyRating, 5 stars1 month ago
We loved staying in this beautiful home in Montalcino. It was even more beautiful and unique than the pictures! My family of five loved staying here- lots of space for everyone and it was fun to be right in the 500 year old town. We especially love having coffee and wine on the balcony.
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
4.85 out of 5 average rating, 39 reviews

La Casetta

LauraRating, 5 stars1 month ago
Beautiful, peaceful stay. Amazing, secluded location. The hosts were very friendly and welcoming - made us feel right at home. Lots of great walks around, including the nearby winery. The only downside is it does get rather cold in the stone apartment but during warmer weather the coolness in the apartment would probably be perfect. They provided a portable heater & a hot water bottle though which was nice. Thank you Tebea for being such a lovely host!
Guest favorite
A stone exterior of a Tuscan-style home is displayed, featuring a covered porch with seating. The garden is green, complemented by an olive tree and blooming purple bougainvillea. Large windows allow for natural light, creating a welcoming outdoor space.
Home in Batignano
4.97 out of 5 average rating, 62 reviews

Nice holiday home in Tuscany (2/3 pers)

PascalRating, 5 stars1 month ago
We had a very pleasant stay at Pascale's and Gian Luca's house. The house is beautiful and very well conceived. We enjoyed the terrace. The kitchen is fully equipped. The appartment was very clean. The area is fantastic for many outdoor activities such as bicycling or sightseeing. Pascale and Gian Luca were easily reachable. We would love to come back.
Top guest favorite
A kidney-shaped pool is surrounded by a well-maintained patio and lush greenery. Several lounge chairs, each with a white frame, are positioned around the pool. An umbrella provides shade over one seating area, enhancing the inviting outdoor space.
Home in Roccatederighi
5 out of 5 average rating, 17 reviews

Private Villas Privacy and Pool

MartinaRating, 5 stars2 weeks ago
We were 9 people and we were all very satisfied with the place, nice quiet, clean. And the landlord was nice and easy to get in touch with. All in all, Mega is a good experience, definitely not the last time we will be away

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Roccastrada
  6. House rentals