
House vacation rentals in Roccastrada
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Top-rated house rentals in Roccastrada
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Popular amenities for Roccastrada house rentals
House rentals with a pool

Private villa/swimming pool in Tuscany
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!

Country house La Meria
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!

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 :)

Gaiole in Chianti Poggio Casabianca
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!

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 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.

Country House w/ heated Pool near the City Centre
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.

Tuscan dream in the ancient Tobacco's villa, sauna
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.

Paluffo Stillo House
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

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!

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!

Il Camino: cosy & artfully inspired country house
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.

Capezzuolo 33
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!

L'Uva Fragolina. House, Garden, Panoramic View
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!

House in the Maremma hills
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!

Casetta Rosa: relaxation between sea and nature
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!

Apartment in the village of Castello di Tocchi
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

Hidden gem in Tuscany
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.

Cozy country house Podere Scorno with pool
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.

New Palazzo in City Center: 4 King Bedrms 6 Bath
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🙏

Bel Casale with sea view and the mediaeval village
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.

Domus Antiqua
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.

La Casetta
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!

Nice holiday home in Tuscany (2/3 pers)
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.

Private Villas Privacy and Pool
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
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- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Gulf of Baratti
- Cala Violina
- Marina di Grosseto beach
- Kite Beach Fiumara
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Avignonesi Winery Fattoria Le Capezzine
- Cavallino Matto
- Cala Di Forno
- Spiaggia Marina di Cecina
- Santa Maria della Scala
- Casa Barthel
- Spiaggia Di Barbarossa
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Zuccale
- CavallinoMatto
- Spiaggia della Padulella
- Spiaggia di Cavo
- Pubblico Palace
- Castiglion del Bosco Winery