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House holiday rentals in Roccastrada

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Popular amenities for Roccastrada house rentals

House rentals with a pool

Guest favourite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars3 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Guest favourite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week 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 favourite
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars2 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!
Superhost
Home in Figline Valdarno
4.96 out of 5 average rating, 108 reviews

The Owl: view, pool and garden

JasonRating, 5 stars4 weeks ago
What a great place to stay while visiting Tuscany. The home is a renovated medieval watchtower located up a dirt road, tucked on a hilltop overlooking the valley. Jacopo, the host, was so kind, hospitable and responsive during our 5-day visit. Would definitely recommend this place to explore Tuscana.
Guest favourite
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 :)
Superhost
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month 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 received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!
Top Guest favourite
Home in Subbiano
4.99 out of 5 average rating, 84 reviews

Romantic cosy flat - Toscana Italy

BeckyRating, 5 stars4 days ago
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.
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.

Weekly house rentals

Guest favourite
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 favourite
Home in Asciano
4.94 out of 5 average rating, 35 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars2 weeks 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 favourite
Home in Sticciano Scalo
4.95 out of 5 average rating, 39 reviews

Villa in Maremma

VickyRating, 5 stars8 months ago
Massimo and his wife were great hosts. His place was ready and clean when we arrived. It had everything we needed. Massimo was always responsive and helpful. We were staying there for a wedding at La Pescaia and Massimo was kind enough to give us rides when needed. He went above and beyond to make us feel at home. I highly recommend Massimo’s place and would love to visit again. Thank you Massimo and Luana!
Top Guest favourite
Home in Pereta
5 out of 5 average rating, 57 reviews

Bel Casale with sea view and the mediaeval village

DennisRating, 5 stars1 week ago
The communication before our arrival was very good, the hostess responded very quickly to messages and also proactively contacted us. We were very warmly welcomed and were even allowed to check in 1 hour earlier. We were shown everything in and around the house. The house and the garden + pool were very clean. The air conditioning in the bedrooms was important and also worked well. In the kitchen you will find everything you need. The garden is beautifully large and well maintained. The large pool with the beautiful view also impressed us. The hosts, who live about 50m next door, took care of the pool every morning and checked if everything is okay there. The directions were also relatively easy. Approximately 30 minutes' drive to the house, there is a large Coop supermarket, where we were shopping. The sea is also only 30 minutes away by car. All in all, we were very satisfied and fully enjoyed our vacation as a group of 6 people!
Superhost
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 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!
Guest favourite
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.
Guest favourite
Home in Gavorrano
5 out of 5 average rating, 11 reviews

House in the Maremma hills

JessicaRating, 5 stars4 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!
Top Guest favourite
Home in Chiusdino
4.91 out of 5 average rating, 46 reviews

La Capanna: country house with magnificent view

VladRating, 5 stars1 week ago
Thomas's Tuscany oasis was absolutely wonderful! It was peaceful and felt like a breath of fresh air. Thomas was extremely accommodating and assisted with everything that we needed. One recommendation for the guests is to just type in the gps coordinates into google maps to find the place a lot easier.

Private house rentals

Top Guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 36 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 favourite
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 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!!!
Top Guest favourite
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, with us, to reserve a tennis court. Full recommendation!
Top Guest favourite
Home in Bivio di Ravi
4.96 out of 5 average rating, 54 reviews

Casa Elicriso

FrancescoRating, 5 stars2 weeks ago
We had a fantastic stay thanks to the hospitality and enthusiasm of Barbara and Emmanuele, who were kind enough to spend unforgettable moments with us, despite their work obligations. The apartment is impeccable: clean, tidy and well organized. Their house is well located in southern Tuscany, not far from cultural and archaeological centers such as Vetulonia, Massa Marittima or Grosseto. Beautiful beaches are only 1/4 of an hour, 20 minutes by car, such as Follonica or Castiglione. In short, if you pass through the area, really don't hesitate, go for it! Warmest regards, Brenda & Francesco
Top Guest favourite
Home in Montalcino
4.94 out of 5 average rating, 33 reviews

Domus Antiqua

KellyRating, 5 stars2 months 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
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.
Guest favourite
Home in Bagno A Ripoli
4.92 out of 5 average rating, 37 reviews

Casa Iperico in Historical Tuscan Villa

DuaRating, 5 stars1 month ago
Bianca is one of the best hosts I ever encountered. She is very friendly, welcoming and social. She is very passionate about her house and guests. She treated us like friends and I think we already became friends for life. Her house is very special, magical, clean and beautiful. Its very spacious felt right at home and had everything we needed. Its private and peaceful yet walking distance from Grassina town down the hill, around 10 minutes walk. The town has everything you need from restaurants to bars, Farmacia, little boutique shops and beauty salons. The location is perfect and outside the city but only 20-30 minutes from Florence. I am defiantly coming back to this place.
Top Guest favourite
Home in Castello di Tocchi
4.97 out of 5 average rating, 62 reviews

Apartment in the village of Castello di Tocchi

AgátaRating, 5 stars3 days ago
We were in Castello for the fourth time and we were satisfied again. We love the old stone house and the tranquility of the forest that surrounds it. We feel at home there. The location of the village is perfect as a starting point for discovering Tuscany. We'd love to come back! Thanks for everything

Destinations to explore

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  4. Province of Grosseto
  5. Roccastrada
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