
House holiday rentals in Castiglione della Pescaia
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Top-rated house rentals in Castiglione della Pescaia
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Popular amenities for house rentals in Castiglione della Pescaia
House rentals with a pool

Infinity pool in Chianti area
"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!

Wonderful country house
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.

[Little Escape] 4 Beds + Private Panoramic Pool
Our stay in Montebenichi was almost indescribable. Having been to Tuscany before, this time was pure magic. The flat is within the compound of a 12th century fortress village that is mostly inhabited by residents. Tommaso had stocked the kitchen with plenty of coffee, milk, water, juices, snacks and his grandmother's amazing Limoncello! The pool area has the most incredible view with an outdoor kitchen where Tommaso arranged for us to have a traditional Tuscan cooking class. He also made reservations for us at the village Michelin-rated restaurant that is just steps from the flat. One of our favorite things was hearing the wolves of Tuscany howl in the distance - no need to be afraid - it was pure magic. We saw very few tourists which made the experience even better. Moreover, Tommaso was THE BEST HOST we have ever had while staying at an Airbnb. His dedication to ensuring the perfect stay for us was truly a standout. We can not say enough good things about our stay!

Charming estate with views
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.

Casa San Ripa: Relax Oasis with Private Pool
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!

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 :)

Collina Power
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!

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 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!
Weekly house rentals

Bouganville apartment between "Sky and Sea
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.

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!

[porto s. stefano] place like heaven + parcheggio
Beautiful apartment in a tranquil environment with a view to die for and all the necessities available. Ideal location for anyone looking for peace and privacy, but still close enough to the town centre, the shops and the restaurants. Excellent and friendly communication with IdealDomus during the stay. Will definitely come back with my friends to enjoy a little bit of la dolce vita in Porto Santo Stefano. Grazie mille!

Casa Middio in Castiglione della Pescaia, 6 guests
We stayed in Cinzia's house for five to ten days and found the accommodation comfortable and well distributed. The double bedroom with a private bathroom is the best. The recently renovated accommodation was very clean and had all the necessary equipment for both the kitchen and the rest. The outdoor area, with its complete and well-kept furnishings, allows you to enjoy lunches, dinners and relaxation in the perfectly shaded garden. Very close to the beach, a half-hour walk from the village, it is the ideal place for those who love tranquility. Cinzia responded immediately to our requests with care and kindness. What can I say, we couldn't have asked for better. Highly recommended.

Casa Elicriso
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

Sensational semi-detached villa - Astonishing view
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!

Villa Pandora: an oasis by the sea
We stayed at Susanna's from April 23rd to 27th and had a great time. Susanna welcomed us warmly and willing to give us all the useful information on places to visit and where to eat the local delicacies. The villa is beautiful and surrounded by greenery and in a quiet area with sea views. Our dogs were also able to roam freely in the garden because they were fully fenced and safely. We will definitely be back. Imma and Luca

Casa Vista Sea and Maremma
We spent 2 weeks in June at Maria's. The handover of the apartment worked smoothly. The apartment has a beautiful view. It is very clean and modern. We had over 30 degrees every day and were very happy about the many shadows on the terrace, the light wind and the outdoor shower. At the table on the terrace you can eat perfectly and the chairs and loungers invite you to read and chill. The apartment is very quiet. You can walk to the old town with many restaurants and bars in 10 minutes. To the beach you need a leisurely 25-30 min. through the old town. Supermarkets can be reached in 5 minutes by car. On departure, we were even allowed to check out after noon.
Private house rentals

The house in the Castle and the secret garden
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 :)

Cozy country house Podere Scorno with pool
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!!!

Villa in Maremma
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!

La Mignola Apartment
Wonderful place, friendly people, beautiful views. We were a family of 4. Here you can rest, relax, think and stop for a moment. You will feel like you are 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, table tennis. You can have a 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 shops. 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 now! Best regards and maybe see you 🤗

Cozy Artist Retreat in the heart of Sorano
We loved our stay here! The house is charming and so unique. We especially loved the beautiful views from our patio and the restaurants nearby. Caleb was a great host and was very responsive. The cats in the area were definitely a huge bonus. We can’t wait to be back!

Casa delle Tortore
We enjoyed the stay at Serena so much. The terrace offers a stunning view 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 their own bathroom. Everything was very clean and well maintained and very stylishly furnished. The kitchen is very well equipped, with 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 come back soon♥️.

Agriturismo Podere San Martino (apartment for two)
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!

La Casetta
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
₹3,462 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
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- Elba
- Giglio Island
- Giannutri
- Feniglia
- Gulf of Baratti
- Cala Violina
- Kite Beach Fiumara
- Marina di Grosseto beach
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Spiaggia di Marina Di Campo
- Spiaggia di Patresi
- Cavallino Matto
- Spiaggia Marina di Cecina
- Cala Di Forno
- Santa Maria della Scala
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Di Barbarossa
- Spiaggia Zuccale
- CavallinoMatto
- Spiaggia della Padulella
- Spiaggia di Cavo
- Pubblico Palace
- Castiglion del Bosco Winery