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House vacation rentals in Castiglione della Pescaia

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Popular amenities for Castiglione della Pescaia house rentals

House rentals with a pool

Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 109 reviews

Infinity pool in Chianti area

KrisRating, 5 stars2 weeks ago
"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!
Guest favorite
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
Home in Campiglia Marittima
5 out of 5 average rating, 32 reviews

La Mignola Apartment

MonikaRating, 5 stars2 weeks ago
Wonderful place, friendly people, beautiful views. We were a family of 4. Here you can rest, relax, think and pause for a moment. You'll feel like you're in paradise. Here you will find something for yourself and your child. Very large, clean swimming pool, jacuzzi, sun loungers, umbrellas. Beautiful orchard. You can play football, ping pong. You can barbecue in the orchard, and in the morning, when you get up, you can drink coffee on the terrace with a beautiful view. The apartment is sensational. Very clean in all rooms. The city is 5 minutes away by car. In the city, there is a variety of stores. You'll find everything you want. From here you can get to many other interesting places. Thank you for the delicious cupcakes from mom Vitorrio, we❤️ wholeheartedly recommend this place Great!!! Don't hesitate! Book! Best regards and maybe see you 🤗
Guest favorite
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.
Guest favorite
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 :)
Top guest favorite
Home in Volterra
4.93 out of 5 average rating, 180 reviews

Collina Power

DeanRating, 5 stars4 weeks ago
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!
Superhost
Home in Sorano
4.8 out of 5 average rating, 128 reviews

Lovely home in villa with garden and pool

JoshRating, 5 stars2 weeks ago
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
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 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!

Weekly house rentals

Top guest favorite
Home in Suvereto
4.96 out of 5 average rating, 48 reviews

The house in the Castle and the secret garden

RebeccaRating, 5 stars2 weeks ago
A beautiful place. You can see and feel it is not just a random vacation rental but feels like someones home and someone has put a lot of detail and love in the place. Once you talk with Diana, you understand even better: as the owner, so the home :) The house offers all you need to stay there (with your whole family) also for longer than only a few nights. The village is very cute and offers all you need, plus charming bars and restaurants. On top it is a great starting point to go and explore the area/ medieval towns/ nature parcs/ beaches. By car it felt like everything is reachable in max 20minutes. Further you can explore by bike and even start from the town on hikes so: if you get a chance to book, stop searching - hit the button and enjoy your time :)
Guest favorite
Home in Giglio Porto
4.94 out of 5 average rating, 18 reviews

Bouganville apartment between "Sky and Sea

MatthewRating, 5 stars9 months ago
Annamaria sent an email with lots of really useful info ahead of our stay and check-in was very easy. She was also responsive to messages and friendly, the perfect Airbnb host - thank you Annamaria. The place itself is almost beyond description - it felt to us like our own piece of paradise. The view from the terrace is breathtaking and having our own private bathing-rock to swim from was really special. We cannot wait to return.
Guest favorite
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!
Superhost
Home in Porto Santo Stefano
4.87 out of 5 average rating, 30 reviews

[porto s. stefano] place like heaven + parcheggio

HaleyRating, 5 stars1 week ago
We had such an amazing stay here! The views from the balcony overlooking the ocean were absolutely breathtaking. We didn’t want to leave! The home was also decorated so cute and was very clean. Can’t wait to come back!
Top guest favorite
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 favorite
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
Guest favorite
Home in Capoliveri
4.97 out of 5 average rating, 69 reviews

Sensational semi-detached villa - Astonishing view

JamesRating, 5 stars3 days ago
Gianfra’s place was really nice, even better than the pictures! Really spacious and the view from the balcony was incredible. Less than a 10 minute walk to the centre of Capoliveri and the same amount of time to the lovely Barabarca beach. Gianfra (and Giusuppe) was a really good host who met us at the house and showed us round and explained everything to us. He even booked us a couple of restaurants and gave us some really good recommendations during our stay! Thank you Gianfra and Giuseppe!
Guest favorite
Home in Castiglione della Pescaia
5 out of 5 average rating, 11 reviews

Villa Pandora: an oasis by the sea

LucaRating, 5 stars1 month ago
We stayed with Susanna from April 23 to 27 and had a great time. Susanna welcomed us warmly and was helpful in giving us all the useful information on places to visit and where to eat local delicacies. The villa is beautiful and is surrounded by greenery and in a quiet area with a sea view. Our little dogs were also able to run around freely in the garden because it was entirely fenced and safe. We will definitely stay again. Imma and Luca

Private house rentals

Top guest favorite
Home in La Pesta
4.82 out of 5 average rating, 49 reviews

The Laurel

AlessandroRating, 5 stars1 month ago
We stayed at "l'alloro" for five days (four nights) and had a very good time. The owners are friendly, they gave us all the information we needed for a comfortable and pleasant stay. The place is sheltered and very quiet. The house is comfortable and clean. We had our large dog with us and we didn't have any problems. Nearby is Lake Accesa, very convenient, but in any case we were not too far from the beaches of Follonica. Great experience.
Guest favorite
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.
Superhost
Home in Castiglione della Pescaia
4.92 out of 5 average rating, 25 reviews

Monte Regio

BarbaraRating, 5 stars11 months ago
I was in Castiglione della Pescaia for a week with my family and dog. I had a really good time at Flavia's place, very clean, very nice location and well-kept garden. I have to say that it is the ideal place to relax and enjoy the tranquility of a vacation.
Superhost
Home in Sorano
4.86 out of 5 average rating, 43 reviews

Cozy Artist Retreat in the heart of Sorano

EleonoraRating, 5 stars1 week ago
Pleasant and peaceful stay. Unique and charming house, comfortable bed and large and nice terrace. We were joined by many cats from the village, which made our stay even more pleasant. Caleb was very helpful, especially for early check-in.
Guest favorite
Home in Porto Santo Stefano
4.9 out of 5 average rating, 60 reviews

Casa delle Tortore

AnjaRating, 5 stars3 days ago
We enjoyed staying at Serena's so much. The terrace offers stunning views of the sea, which is not far away and has beautiful beaches. The apartment was perfect for our three children, who had plenty of space and a private bathroom. Everything was very clean and well maintained and very stylishly furnished. The kitchen is very well equipped, with a dishwasher, washing machine, WiFi and even a table tennis table, nothing was left to be desired. In addition, Serena and her husband Giulio are incredibly nice and helpful. We hope to be back soon♥️.
Top guest favorite
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!
Top guest favorite
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
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.

Quick stats about house rentals in Castiglione della Pescaia

  • Total rentals

    60 properties

  • Nightly prices starting at

    G$8,364 GYD before taxes and fees

  • Total number of reviews

    710 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore