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Villa vacation rentals in Castiglione della Pescaia

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Popular amenities for Castiglione della Pescaia villa rentals

Private villa rentals

Superhost
An oceanfront villa features a unique pool area blending with the rocky coastline. Loungers surround the pool, positioned on a stone deck. The building's façade showcases natural stone, and large windows offer views of the sea and surrounding greenery.
Villa in Rosignano Solvay-Castiglioncello
4.79 out of 5 average rating, 140 reviews

Villa con piscina sulla scogliera

TatianaRating, 5 stars2 weeks 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.
Guest favorite
The villa is situated atop rocky cliffs, surrounded by lush greenery, showcasing a blend of natural beauty and architectural charm. The structure, featuring a terracotta roof and multiple arched windows, offers stunning views of the tranquil blue sea below.
Villa in Giglio Porto
5 out of 5 average rating, 11 reviews

Villa in esclusiva " Cielo e Mare"

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
A spacious living and dining area features a vaulted wooden ceiling and a blend of modern and vintage furnishings. A large table with yellow chairs sits in the center, surrounded by a comfortable green sofa and an armchair. Bright curtains frame windows that invite natural light.
Villa in Grosseto
4.88 out of 5 average rating, 25 reviews

Cheerful Villa with Pool First Floor

FernandaRating, 5 stars10 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 favorite
A sparkling pool is set in a well-maintained lawn, surrounded by tall trees and cypress plants. Comfortable lounge chairs are positioned beside the water, with a shaded area provided by an umbrella. The rustic villa can be seen in the background against a clear blue sky.
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 favorite
The aerial view captures the charming layout of Monticchiello, showcasing terracotta-roofed buildings surrounding a lush green garden adorned with soft lighting. A winding pathway leads to the garden, providing a serene outdoor area amidst the medieval architecture.
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa con giardino. Il Giardino del Cardinale.

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.
Top guest favorite
The rustic two-story house is enveloped in lush green ivy, highlighting its stone façade. Two arched doors are framed by natural greenery, creating a harmonious appearance. An outdoor dining area with a table is partially visible under a shaded patio, providing a serene setting in the garden.
Villa in Sovicille
4.95 out of 5 average rating, 73 reviews

Beautiful Country House, near Siena with jacuzzi

JohannaRating, 5 stars3 weeks ago
Unser Aufenthalt in diesem wunderschönen Haus in der Toskana war einfach traumhaft! Das Haus liegt idyllisch am Land und hat all unsere Erwartungen übertroffen – es war noch schöner als auf den Bildern. Alles war sehr geschmackvoll eingerichtet, sauber und perfekt ausgestattet, um entspannte Tage inmitten der toskanischen Natur zu genießen. Die Gastgeber waren ausgesprochen freundlich und hilfsbereit – von der unkomplizierten Ankunft bis hin zu tollen Tipps für Ausflüge in der Umgebung waren sie immer für uns da. Wir können dieses Haus wärmstens weiterempfehlen und würden jederzeit wiederkommen!
Guest favorite
A dining table is set outdoors, surrounded by olive trees. It features white plates, glasses filled with red wine, and a selection of cheese. In the background, sweeping views of the Valdichiana and the medieval village of Scrofiano are visible under a partly cloudy sky.
Villa in Scrofiano
4.86 out of 5 average rating, 94 reviews

SacroFanum Villa

ClaudiaRating, 5 stars1 week ago
Wir hatten eine wundervolle Zeit in der Villa! Die Aussicht auf die toskanische Landschaft und auf Scrofiano ist einfach atemberaubend . Der Pool war ein echtes Highlight: gepflegt, ruhig gelegen und perfekt, um die Seele baumeln zu lassen. Manola und Martha waren sehr freundlich und hilfsbereit, standen bei Fragen jederzeit zur Verfügung. Insgesamt eine rundum entspannte Zeit – wir kommen bestimmt wieder!
Top guest favorite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti
4.98 out of 5 average rating, 49 reviews

Sestuccia

AnnieRating, 5 stars1 month ago
This was the most magical place so spend a week in Chianti! The villa is exceptionally beautiful, and has everything you could need for a comfortable stay. The grounds were spectacular, with many things to do and different areas to sit and enjoy. My toddler especially loved picking strawberries from the small garden and collecting eggs from the chickens for breakfast. The hosts were lovely and helpful with any questions we had, and took great care of us. The town of Gaiole in Chianti is very close and with great restaurants and things to do. A perfect spot I can’t recommend highly enough!

Luxury villa rentals

Top guest favorite
A private swimming pool is surrounded by stone walls and olive trees. The inviting clear water reflects the blue sky. In the background, a rustic house with stone walls and a broad archway is visible, along with a pool house featuring a textured exterior.
Villa in San Giovanni d'Asso
5 out of 5 average rating, 25 reviews

Pasqui Villas : Tribbio private house pool WiFi

EmilyRating, 5 stars3 weeks ago
We stayed at this Villa for just under a week with 2 families and had the most amazing time. It was absolutely perfect. SO much space (2 kitchens, 3 living rooms, 7 bathrooms!!!!) The pool and grounds around the home are stunning and they take such great care of it. You can tell this is a family home that Federica and her family take great pride in. Federica and her son welcomed us at the villa and they were super responsive before and during our stay. They also recommended a lot of things like a driver for a wine tour, chef that came and cooked for us a couple nights (so delicious), etc. Am very sad to not be at this dreamy villa anymore and hope to go back at some point in the future. Highly recommend!!
Guest favorite
The exterior showcases a spacious garden area featuring several lounge chairs positioned on lush green grass. A stone pathway leads towards the welcoming entry of the two-story villa, framed by trees and flowering plants under a partly cloudy sky.
Villa in Siena
4.97 out of 5 average rating, 39 reviews

Capanna Di Elfo

MichaelRating, 5 stars1 month 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.
Top guest favorite
A refreshing salt-water pool is surrounded by a stone patio and greenery, offering sun loungers for relaxation. A shaded gazebo with a table provides an outdoor dining option, while the rustic villa with a tiled roof sits adjacent, blending harmoniously with its natural surroundings.
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa Mulino del Cerchiaio

MathildeRating, 5 stars8 months ago
Merci !! Nous avons bien profité de nos vacances entre copines à 9 ! Un peu d’humidité du fait du temps, mais l’endroit est idéal en été et réconfortant au coin du feu quand le beau temps n’est pas présent !
Superhost
The villa is positioned on a rocky coastline, surrounded by greenery. The vibrant blue waters reflect sunlight, creating a serene atmosphere. The property features a terrace lined with flowering plants, accessible from the upper level, enhancing the natural integration with the surrounding landscape.
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
A serene outdoor area features a clear swimming pool, surrounded by lush greenery and neatly arranged landscaping. The stone house has a spacious balcony above, offering additional seating options and views of the countryside.
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 Persone - Piscina Privata

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.
Top guest favorite
The historic villa is set amidst a lush green lawn, showcasing traditional brick architecture and arched windows. Surrounding foliage includes well-maintained shrubs and trees, accentuating the serene countryside ambiance.
Villa in Siena
5 out of 5 average rating, 13 reviews

L’Apparita del Peruzzi,pool,super view,save30%7d+

AlexanderRating, 5 stars6 days ago
An enchanting place. The villa is steeped in history and the gardens with a small amphitheater and a distant view of Siena are spectacular. Great location from which to explore the rest of Tuscany. My family and I have enjoyed our stay.
Superhost
An aerial view showcases the expansive Tuscan villa surrounded by lush greenery. The property features a large private pool and well-maintained garden areas. Gravel pathways and olive trees frame the villa, which is built in traditional Tuscan style, with a terracotta roof and stone façade.
Villa in Libbiano
5 out of 5 average rating, 4 reviews

Exclusive Tuscan Villa with private pool

KepaRating, 5 stars1 month ago
Hemos pasado unos días fantásticos en la propiedad de Andrea. El lugar es una maravilla, en un entorno muy tranquilo, con zonas amplias para descansar y un jardín fabuloso con piscina y barbacoa para planes de amigos cuando el tiempo lo permite. Las habitaciones son amplias y silenciosas y con baño, lo que las hace muy cómodas. Andrea es, además, un gran anfitrión que nos proporcionó gran cantidad de recomendaciones y sugerencias de restaurantes y otras actividades para hacer en los alrededores de la casa. Las que pudimos probar, fueron un acierto. Un lugar muy recomendable donde a buen seguro nos gustaría volver en alguna otra ocasión.
Top guest favorite
A spacious outdoor area featuring a large swimming pool surrounded by sun loungers and shaded seating under a white canopy. Lush green gardens and neatly trimmed hedges are visible, with surrounding hills and cypress trees enhancing the serene landscape.
Villa in Bucine
4.98 out of 5 average rating, 43 reviews

Villa Tontenano Capannole Chianti private pool 12

IndunRating, 5 stars3 weeks ago
This place is fabulous. Margherita was responsive so quickly. We had a 11 people six adults and five kids. Loved the pool and hot tub. Margherita made reservations for us and suggested day trips. She even got a wheelchair for me for the Hill towns. Take advantage of their cooking. they did meals for us, which were fantastic. And even organized a birthday dinner for the three young girls. They did the birthday cake and even gave them a gift. It was fabulous. Don’t hesitate to book. We did day trips to Sienna, pisa,Luca, panzano, pienza and multipulciano. And two trips to the luxury mall.!Her parents are so helpful too. Olive oil and their wine is fantastic. The only regret I have is that we didn’t have extra days and spend the time right around villa. I think we would have really enjoyed the wine tasting and olive tastings. I would’ve stayed easily another week. Do take advantage of her massages too. My kids thoroughly enjoyed our visit. It exceeded my expectations!!!!! Ten stars!!!!!!

Villa rentals with a pool

Superhost
The outdoor area features a sparkling pool surrounded by lush greenery and stone walls. Comfortable lounge chairs offer relaxation, while decorative plants and a stone staircase enhance the natural setting. Bright blue skies and ample sunlight contribute to a serene atmosphere.
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
La famiglia che ci ha accolto è stata molto disponibile, la location è super. Abbiamo trascorso dei giorni di relax nella tranquillità degli ulivi. Posizione strategica per raggiungere sia le spiagge a Nord che a Sud dell'isola. Persone gentili e conviviali. Consigliatissimo!
Superhost
An inviting living space features high ceilings with exposed wooden beams. A rustic wooden dining table occupies the center, adorned with a green decorative bottle. Bookshelves line the walls, filled with books, while a comfortable couch is positioned in the corner, creating a cozy atmosphere.
Villa in Pomaia
4.69 out of 5 average rating, 45 reviews

Podere San Luigi - a real Tuscan experience

PeterRating, 5 stars8 months ago
We really enjoyed our stay in the house. It was exactly what we were looking for. A charming place equipped like a home with everything you need - even an EV charger. The house keeper was very helpful and responded promptly to all our questions. We would be happy to come back another time.
Top guest favorite
The villa is presented with warm sunlight streaming over the scene, showcasing its inviting exterior and surrounding hills. A spacious porch is visible, accompanied by landscaped areas and a swimming pool in the background. Natural greenery complements the tranquil setting.
Villa in Cinigiano
5 out of 5 average rating, 45 reviews

Scacciapensieri. Cottage in Tuscan Country

KoenRating, 5 stars1 month ago
Geweldig vakantiehuis met prachtig uitzicht over de Toscaanse heuvels. Maar liefst 3 ruime slaapkamers met prima bedden. Een fijn overdekt terras met hetzelfde prachtige uitzicht waar je heerlijk kunt ontbijten of dineren. Het privezwembad is natuurlijk ook fantastisch, onze kinderen hebben hiervan genoten. Gabriele is een zeer vriendelijke proactieve host die vantevoren allemaal leuke tips en handige info stuurde en onze zelf opwachte bij aankomst. Ondanks het iets mindere weer tijdens de week dat wij er zaten is er vanalles te doen en te bezoeken in de omgeving, bij mooi weer kun je ook nog naar de kust. Ik zou dit verblijf van harte aanraden en hoop er ooit nog terug te komen!
Guest favorite
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!
Superhost
A charming outdoor dining area is presented, featuring a round table surrounded by four wicker chairs with red cushions. A gentle sunset casts a warm glow, while the distant silhouette of San Gimignano towers over the lush green landscape in the background.
Villa in San Gimignano
4.79 out of 5 average rating, 19 reviews

Casale Esclusivo Piscina & vista su 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!
Guest favorite
A clear swimming pool occupies the central focus, featuring steps leading into the water. Surrounding the pool, loungers with umbrellas are placed on a grassy area, complemented by greenery and soft landscaping in the background. Solar panels are visible on the roof of the adjacent structure.
Villa in Cecina Marina, Cecina
4.97 out of 5 average rating, 37 reviews

Luci di Maremma bilocale con piscina, mare, pineta

NadineRating, 5 stars2 weeks ago
Wir haben unsere Sommerferien mit 2 Kindern (vor Saisonstart) für 2 Wochen verbracht. Es hat uns allen herrvoragend gefallen und wir haben uns auf Anhieb sehr willkommen gefühlt. Die Gastgeber sind sehr hilfsbereit und doch nicht aufdringlich. Sie lassen einem sehr viel Privatsphäre. Nach einer Woche wurden wir proaktiv gefragt, ob wir neue Frottée- und Bettwäsche möchten. Die Kinder waren sehr willkommen. Der saubere, grosse und kostenlose Strand erreicht man über eine Privatstrasse, welche mit Velo oder Auto befahren werden kann. Es war einfach wunderschön und wir werden sicherlich wieder mal zurück kommen.
Top guest favorite
A stone house is observed in the background with a sloped roof and a covered patio area. In the foreground, a rectangular swimming pool reflects the sky, surrounded by a grassy area and lounge chairs. Trees are visible, adding greenery to the serene setting.
Villa in Sorano
4.98 out of 5 average rating, 98 reviews

Poggio Bronzino, Montebuono - Sorano (Gr)

ChristianRating, 5 stars1 week ago
Tolle, großzügige Villa mit wunderschönem Pool und Aussicht auf den Sonnenuntergang. Wir haben uns sehr wohl gefühlt und die Zeit sehr genossen. Absolute Weiterempfehlung!
Guest favorite
A clear blue pool is bordered by terracotta tiles and flanked by lounge chairs under a large umbrella. Lavender plants add a touch of color in the foreground. In the background, a landscaped garden and villa create a serene outdoor space.
Villa in Tignano
4.95 out of 5 average rating, 174 reviews

Villa Isabella

AndrewRating, 5 stars3 days ago
Wow! Christina’s property is beautiful! The surrounding Tuscan hills make for a breathtaking setting, with wonderful views to the east and west for sunrise and sunset. We enjoyed drinking in the views from the terraces and while cooling off in the pool, which was a great size and bigger than we had imagined from the pictures. Watching the local swallows, who would soar overhead and drink from the pool, was a real treat. The villa itself was spacious, clean and thoughtfully decorated. Christina was a wonderful host, ready to greet us on arrival and to help us check-out, and responsive to all our messages. She even bought us a lilo for the pool when I asked if there was one! Christina had lots of suggestions of local things to do, from the best artisanal butcher from whom to purchase bistecca alla fiorentina, to where to buy the finest locally produced olive oil and Chianti. We hope to return, a real treat! Grazie mille, Christina!

Destinations to explore