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Villa holiday rentals in Castiglione della Pescaia

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Popular amenities for villa rentals in Castiglione della Pescaia

Private villa rentals

Guest favourite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars1 week ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 28 reviews

Sestuccina

RubyRating, 5 starstoday
Beautiful place to stay! • Super nice location (lots of nature and very quiet) • Communication always runs smoothly • Great restaurants and delicious ice cream within 5 minutes' drive • Equipment exactly as specified I would recommend it again and again! Luciano and Brigitta are great hosts 😊
Guest favourite
Villa in Giglio Porto
5 out of 5 average rating, 11 reviews

Exclusive "Cielo e Mare" villa

JonathanRating, 5 stars11 months ago
Woooow, no words can really describe how wonderful this place is. We've seen this fantastic villa from afar before (you can see it when coming in to the island from the boat), but we could never imagine how wonderful it is. The house itself is perfect, with plenty of bedrooms, bathrooms etc - but what really stood out was how close you were to the city while also feeling like having your own little paradise. The balconies where a dream, the view perfect and the private place to swim simply wonderful. 10/10, and will 100% come back!
Superhost
Villa in Castiglione d'Orcia
5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

MiaRating, 5 stars1 month ago
We were looking for a villa that had plenty of space for my husband and I with our 3 adult kids and this villa was perfect! We all had our own bedrooms and private bathrooms. The villa was in the idyllic peaceful Tuscan countryside surrounded by rolling hills, wine vineyards and olive trees with distant views of castles. It is absolutely gorgeous! Alessandro, the owner of the villa met us upon check in. The property has been in his family for hundreds if years. He was incredibly kind and generous, leaving an abundant amount of fruit, several bottles of wine from his vineyard and beautiful fresh flowers in every room. He was always available to answer any questions and make recommendations. Anke, the property manager, was excellent and responsive. Promptly answering my questions prior to the trip and proactively giving us wonderful recommendations. Highlights were truffle hunting Il Podere Castle, Umbria Olive oil tour and Banfi Castle wine tasting. Memories to last a lifetime! ❤️
Top guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 148 reviews

Tuscan farmhouse with private pool and views

MelissaRating, 5 stars6 days ago
Incredible! We had such an amazing time staying here. Charly & Ann have done it up so beautifully. The views are incredible and it’s so peaceful. They went above and beyond answering any questions and recommended an amazing winery to visit! Would highly recommend a visit to this beautiful home. Thank you Charly & Ann
Top guest favourite
Villa in Sovicille
4.96 out of 5 average rating, 72 reviews

Beautiful Country House, near Siena with jacuzzi

DanielRating, 5 stars4 weeks ago
We had a wonderful time at the estate. We were visiting with 4 adults and 2 little babies. The communication with David was always super prompt and he even really quickly helped us out in finding a doctor when our daughter got sick during the stay. The house has everything you need and is well equiped. We cooked every evening in the cosy kitchen and had wonderful breakfasts in the garden. The Jacuzzi overlooking the valley was also a nice spot for relaxing in the warm water. Overall we can just recommend this historic but well modernized house as your idyllic getaway in Tuskany.
Guest favourite
Villa in Lucignano
4.88 out of 5 average rating, 24 reviews

Unique Villa in Tuscany

KeithRating, 5 stars2 weeks ago
A stunning property, completely private and quiet. Large outdoor heated pool was well maintained with perfect outdoor eating and sitting areas. We ate out on the terrace every night. Luc recommended the closest Osteria which we all loved, and also recommended the spot to see those iconic views of Tuscany with the avenues of cypress trees. All 6 of us had joyful experience. Highly recommended.
Superhost
Villa in Castiglione della Pescaia
4.87 out of 5 average rating, 23 reviews

Beach house with parking and garden

SimonaRating, 5 stars9 months ago
It was our first experience and we couldn't find a better Host than Jacopo. Always present, helpful and friendly. It made us feel at home. Absolutely nothing was missing, including the iron and iron, as well as everything strictly necessary for the stay. We will definitely be back and highly recommend it to those who want to visit Castiglione della Pescaia and they are nearby.

Luxury villa rentals

Superhost
Villa in Porto Ercole
5 out of 5 average rating, 11 reviews

Villa Isolotto, by the sea at Argentario

GiuseppeRating, 5 stars9 months ago
Isabella’s place is beautiful and peaceful. The villa is exactly as in the picture and offer lots of common spaces were to relax and play, it is super clean and very well decorated, feels like home. The garden and the view are to die for. Waking up in the morning and see the sunrise over the sea was pure magic. The direct access to the sea was definitely a plus and we really enjoyed it . We recommend this place with no hesitation and we really hope to come back again. This place is a true gem, you won’t be disappointed and Isabella is a great host. Thank you for having us!
Guest favourite
Villa in Peccioli
4.92 out of 5 average rating, 12 reviews

Luxury villa with Pool, games room & Bocce court

KathleenRating, 5 stars8 months ago
My family and I -- six adults and a 9 month old -- spent two delightful weeks at Il Granaio. Before our arrival, Greg (the host) put me in touch with Ally, the property manager, who provided much useful information in advance and ensured we could find our way to the hidden gem that is Il Granaio. Once we arrived, Ally was available as needed, responsive to my queries as we settled in. We enjoyed the Villa and property immensely, using it as a base camp as we did day trips all around Tuscany and a longer visit to the Ligurian coast. The house was comfortable, attractive, and well-outfitted, with fantastic views from the second floor; the surrounding countryside was peaceful and beautiful; the pool was a perfect place to cool off and relax after being out and about; and the billiard table provided enjoyment for all! And having our own washer and dryer was incredibly convenient, especially when traveling with a baby. Wonderful memories were made for our family at Il Granaio!
Guest favourite
Villa in Siena
4.97 out of 5 average rating, 39 reviews

Capanna Di Elfo

MichaelRating, 5 stars3 weeks ago
The property was comfortable, spacious and spotlessly clean. The owners of the property , Claudio and Angelica, are helpful and delightful. However, the “host” BoMVillas , who acts as a middleman, was rude and disrespectful when we had a miscommunication. I would not make another booking that was offered by BoMVillas.
Guest favourite
Villa in Pergine Valdarno
4.95 out of 5 average rating, 87 reviews

La Vignaccia (Farmhouse) - villa w/private pool

DominicRating, 5 stars1 month ago
La Vignaccia is wonderful. We were a family of 6 adults plus a baby, and the set up was great for spending time together but also having plenty of space. The kitchen is well equipped for cooking for a large group and the many private spaces were very relaxing. Working remotely was possible with the wifi but not super strong for calls. However there is 5G around the house, so hot spotting from a window worked fine.
Top guest favourite
Villa in Asciano
4.95 out of 5 average rating, 79 reviews

Podere on the Crete Senesi

NahkitaRating, 5 stars3 weeks ago
We could not have asked for a more beautiful setting to celebrate my partner’s 40th birthday. Our week was perfectly balanced between visiting nearby Montalcino wineries & surrounding villages, a day trip to Siena, and lazing about the pool & villa. Monica was kind, generous & helpful from the time of booking. She accommodated all requests and even left a gift for my partner to celebrate his birthday! Will be back! Would rate this 6 stars if we could.
Top guest favourite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars3 weeks ago
Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.
Superhost
Villa in Isola d'Elba
4.85 out of 5 average rating, 39 reviews

Luxury Villa on the sea Elba Island (Procchio)

FlorentineRating, 5 stars8 months ago
Wonderful villa and grounds with private sea access and lounge area in the rocks. Tastefully renovated older villa, very attentive hosts who helped with any of the minor issues we had. Nice pellet oven was great as the weather was a bit cool. Wonderful place and view.
Superhost
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 People - Private Pool

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.

Villa rentals with a pool

Superhost
Villa in Campo nell'Elba
4.91 out of 5 average rating, 34 reviews

Relax in the countryside near the sea(Olivo)

LuciaRating, 5 stars9 months ago
The family who welcomed us was very helpful, the location is super. We spent days relaxing in the tranquility of the olive trees. Convenient location to reach both the north and south beaches of the island. Gentle and convivial people. Highly recommended!
Top guest favourite
Villa in Siena
4.95 out of 5 average rating, 39 reviews

Villa Le Tortore private luxury pool relaxation Siena

AifricRating, 5 stars4 days ago
We spent six nights in June at this gorgeous house. Thiago was so welcoming and the house was pristine and comfortable with great air conditioning. We loved relaxing and cooling off in the pool which was clean and well maintained. Siena is beautiful and about 15 minutes walk from the house. We loved our stay, it was perfect for our family holiday. Thank you Thiago!
Top guest favourite
Villa in Cinigiano
5 out of 5 average rating, 45 reviews

Scacciapensieri. Cottage in Tuscan Country

KoenRating, 5 stars1 month ago
Great holiday home with beautiful views over the Tuscan hills. No less than 3 spacious bedrooms with great beds. A nice covered terrace with the same beautiful view where you can have delicious breakfast or dinner. The private swimming pool is of course also fantastic, our children enjoyed this. Gabriele is a very friendly proactive host who sent all nice tips and useful info in advance and awakened our self upon arrival. Despite the slightly inclement weather during the week we were there, there is plenty to do and visit in the area, when the weather is nice you can also go to the coast. I would highly recommend this stay and hope to come back someday!
Top guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Superhost
Villa in Rosignano Solvay-Castiglioncello
4.79 out of 5 average rating, 140 reviews

Cliffside villa with pool

TatianaRating, 5 stars1 week ago
We chose this location as the first place to stay for our honeymoon trip and we really relaxed there. It was so quite, so calm, so intimate, it felt like home. The pool was clean, the view was amazing, so amazing that we preferred to prepare food or to buy something warm from the nearest Coop market and to eat it on our terrace than to go to a restaurant. The kitchen is small, you can prepare there only simple dishes. I totally recommend this house if you want privacy and a relaxing holiday.
Superhost
Villa in Grosseto
4.88 out of 5 average rating, 25 reviews

Cheerful Villa with Pool First Floor

FernandaRating, 5 stars9 months ago
Ilaria’s villa is a comfortable and stylish base from which to explore all the wonders that Maremma has to offer. We are a family of four, and after a couple of weeks in Italy, the kids were craving home-cooked meals, so we spent several hours in the kitchen and dining areas. It was delightful to cook while listening to the kids having fun in the pool. The beds were very comfortable and inviting. The villa is conveniently located near the old town center and several supermarkets. Since we were keen to visit Porto Ercole, Alberese, and Saturnia, we didn’t dedicate as much time to Grosseto as we should have. The old center has a very mellow vibe, and everyone we met was very friendly and welcoming. We wished we could have stayed longer. Finally, I want to say a big thank you to Ilaria for being so accommodating and kind. We are already looking forward to returning to your place.
Top guest favourite
Villa in Marciano della Chiana
4.95 out of 5 average rating, 78 reviews

La Bacaia

JorgeRating, 5 stars1 week ago
We thoroughly enjoyed our stay. The house is conveniently located in the heart of the Valdichiana with easy and clear access to the surrounding towns. The grounds were beautifully landscaped with a combination of olive trees, grapevines, flowers and even herbs like rosemary, basil and mint that we used in our cooking. The rooms were spacious and very private. Our group of 6 were more than comfortably accommodated, each with its own bathroom and AC units that worked well. The two kitchens served us well. We mainly utilized the outside kitchen as the weather throughout our stay was perfect. The kitchens were well stocked with all of the necessary cooking items. There were some items that we needed to purchase at the local supermarket, including shower gel, paper towels, napkins, etc. For a one week stay we would recommend extra towels, especially for the pool. Overall, I would highly recommend La Bacaia as a base to fully enjoy your Tuscan vacation.
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 19 reviews

Exclusive Farmhouse Pool & View of San Gimignano

AlineRating, 5 stars1 month ago
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!

Destinations to explore