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

S.Ilaria - Private pool Villa with 2 bedrooms
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!

Antico Borgo Ripostena – n. 9 Oil Mill
Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.

[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!

Relax in the countryside near the sea( Lavanda )
Everything was perfect, super cozy and beautiful place. Isabella and her family welcomed us in the best possible way and met all our requests during our GTE in Elba. Very clean apartment, cozy with fantastic pool, lovely and well-kept place. Thanks again for your hospitality and for meeting our requests

La Mignola Apartment
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 🤗

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.

Country House in the Crete Senesi
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!

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 :)
Weekly house rentals

The Laurel
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.

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 :)

[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!

Monte Regio
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.

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!

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!

Casa delle Tortore
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♥️.

La Bandita Dependance
We picked the location based on (very last minute) availability Airbnb’s. Both the city and Airbnb did not disappoint. The house was very chill and provided us with plenty of privacy and met all our needs. Azzurra was very helpful. And the city (with help of Azzuras tips) provided us with the relaxation we were looking for. Wish we booked a longer stay. Only recommendation for future guests, a car is required to navigate through the area.
Private house rentals

Vacation home - Vento di mare
We were guests at Mariapia's place for a wonderful week. The information and directions were very helpful. The self check-in is completely straightforward. The apartment is very tasteful and clean as described in the listing. The outdoor area is beautifully designed with a spacious garden, where you can have a wonderful breakfast under apricot trees and mistletoe. All in all exactly what we wanted, quiet location and yet in a few minutes to countless entrances to sandy beaches and the sea. Thank you for the wonderful time. I'm sure we'll be back.

Cozy country house Podere Scorno with pool
Very local experience ~ It's also great to be able to experience local life!It's like going back to the environment and house when I was a kid. The stay was very comfortable!The host is also very nice!!!Gave a lot of recommendations!!!Thank you very much!!!

LA RONDINAIA. AMAZING VIEW ABOVE THE CHIANTI
Sebastiano’ place a real heaven in the heart of Chianti mountains in Tuscany. Amazing project, wonderful nature and history everywhere around. Place is so peaceful and unique. Just a dream which came true!

The nest by the sea
Had a great stay at Michele's! The apartment is very newly renovated and has everything you need. We visited during the off-season so we were grateful for the stove providing us warmth in the evenings. Michele was very friendly and helpful, being flexible with our check in and check out times. The apartment is open, except for the bathroom but we made it work just fine. Rio is a nice and quiet little town with a beautiful view and perfect to chill out and relax. Its not far from the ocean either, so with a short drive you will be at the beach. All in all a great place :)

"Il Frassino" Country House
Our stay was perfect all around! We immediately felt at home. The accommodation is not only convincing because of the great location and surroundings, it was also wonderfully furnished and there was nothing missing. We would like to emphasize the warm hospitality of Ranieri. He was always available and helpful. We would come back.

Casa Iris (with jacuzzi) - Close to San Gimignano
Sylvia was an amazing host from the beginning! She came to meet us at the check-in and made sure all our needs were met any time of the day. She was very sweet and made us feel right at home! The place has a very nice hot tub facing the mountains and it gave us some beautiful sunset views! 10/10 would recommend!

Beach house - sleeps 7
Check-in worked out excellently. Host couple very nice and uncomplicated. The house was very clean. The location is fantastic. To the front the sea and behind the house a pine forest, playground. Bakery, vegetable shop, cafe and shopping center within walking distance (5 minutes on foot). I recommend this house with a clear conscience.

Casa La Caletta
I'd rather keep it a secret... but it's a unique spot just to be there and enjoy the atmosphere, peace and sunsets.
Quick stats about house rentals in Castiglione della Pescaia
Total rentals
60 properties
Nightly prices starting at
G$8,368 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
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- Elba
- Giglio Island
- Giannutri
- Feniglia
- Gulf of Baratti
- Cala Violina
- Marina di Grosseto beach
- Kite Beach Fiumara
- 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