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Villa vacation rentals in Castiglion Fiorentino

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Popular amenities for Castiglion Fiorentino villa rentals

Private villa rentals

Superhost
A scenic pathway leads through a lush green landscape, bordered by flowering lavender and vibrant red blooms. The pathway is flanked by neatly trimmed trees, creating a serene and inviting atmosphere that connects the property to the natural surroundings.
Villa in Poppi
4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Superhost
Villa in Chiusi
4.67 out of 5 average rating, 3 reviews

Tuscany 2 Villas sleeps 12 private heated pool

PiotrRating, 5 stars45 months ago
In reality villas present themselves a lot prettier than in photos on website. The area and surroundings are beautiful, calm and quite. Place is perfect as exit basis for exploring and sightseeing Tuscany. Rooms and beds are adequately big and clean. Kitchen and utensils are in sufficient quantity. Pool is clean, water warm. There’s no need for a battle for lawn chairs. Jacopo is very helpfull, communicative, serves his help everyday. The place is worthy of recommendation. We spent our holiday time comfortably in quaint area. All the best!
Guest favorite
An aerial view showcases the villa nestled in lush greenery, surrounded by mature trees. The rectangular swimming pool is visible, accompanied by sun loungers and umbrellas. The rustic stone building features a terracotta roof, blending harmoniously with the natural landscape.
Villa in Umbertide
4.92 out of 5 average rating, 12 reviews

Villa Comunaglia - Design Villa with Private Pool

AnneRating, 5 stars8 months ago
Superbe emplacement en hauteur de la campagne et des collines d’Ombrie. Vues magnifiques depuis la maison et le jardin. Équipement parfait et les 2 maisons permettent de séparer les adultes des plus jeunes ce qui a participé au déroulement très agréable des vacances familiales.
Top guest favorite
A serene infinity pool extends towards a lush forest backdrop, featuring several sun loungers adorned with yellow towels. The sun-drenched patio is made of natural stone, inviting relaxation while showcasing expansive views of the surrounding greenery and distant hills.
Villa in Gaiole in Chianti
5 out of 5 average rating, 20 reviews

Montemarcoli

RobertRating, 5 stars2 weeks ago
Our stay at Villa Montemarcoli was fantastic. So peaceful. No noice from cars and really no air traffic noise whatsoever. Just the birds singing. Just want to mention you will need to drive to everything but the roads are so beautiful you won’t mind! I would recommend a small SUV or car with all wheel drive as the villa is located up a gravel road and roads in the area can be narrow and parking can be tight in places. I would definitely recommend Brigitta’s Villa and hope to come back again someday 😎🍷
Guest favorite
A spacious courtyard is surrounded by rustic stone buildings, featuring an outdoor seating area with terracotta pots and greenery. The paving stones create a welcoming gathering space, while the clear blue sky above enhances the tranquil setting.
Villa in Reggello
4.87 out of 5 average rating, 30 reviews

Villa Arianna, la tua villa in Toscana

JulianaRating, 5 stars6 months ago
Oscar foi muito simpático e gentil conosco! Sua casa é linda e confortável, estávamos em um grupo de 13 pessoas e ficamos tranquilamente hospedados. Lindas decorações e paisagens. Nota 10.
Guest favorite
A well-kept garden area is visible, featuring a stone table surrounded by lush greenery. The structure is framed by mature trees, providing shade and a sense of tranquility. Arched windows of the villa can be seen in the background, offering glimpses of the interior.
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio nelle campagne toscane

LizRating, 5 stars7 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Superhost
A two-story villa is surrounded by a lush green lawn and tall trees. Two lounge chairs are positioned on the grass, inviting relaxation. The building is made of stone and wood, featuring balconies that overlook the landscape of vineyards and Tuscan hills.
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suite & Ville - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars4 months ago
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!
Top guest favorite
A shaded seating area is positioned adjacent to a sparkling pool, surrounded by lush gardens and olive trees. Comfortable wicker sofas with soft green cushions invite relaxation, while sun loungers positioned under umbrellas enhance the outdoor leisure experience. Scenic views of the countryside are visible in the distance.
Villa in Cavriglia
4.99 out of 5 average rating, 128 reviews

Villa Poggio a Mandria in Chianti

EmilyRating, 5 stars6 months ago
We spent a week at Villa Poggio a Mandria as part of a group of six adults and had the most incredible and magical time. The photos do not do justice to how extraordinary the villa and surrounding area are — it’s nestled in an olive grove near the top of a hill just a short walk from a medieval village (Montegonzi), with utterly spectacular views in every direction. It could not be more peaceful or breathtaking. The villa was spotless, gorgeous and fully equipped, with tons of space for everyone. We had an unforgettable day with Lorenzo (contact available through Claudia and Leonardo), a local tour guide and chef who took us on an amazing wine tour and then cooked us the best meal ever that evening. And Claudia and Leonardo are the kindest, most responsive hosts, always available to answer any questions we had and even baking us a beautiful cake one evening! We can’t recommend Villa Poggio a Mandria enough. We had an unforgettable trip that truly felt like a dream. Thank you!

Luxury villa rentals

Guest favorite
A spacious dining area is featured, complete with rustic wooden beams and a large wooden table. Surrounding chairs and a cozy seating area with plush couches create an inviting atmosphere. Natural light filters through multiple windows adorned with greenery, enhancing the room's warmth.
Villa in Sodo
4.95 out of 5 average rating, 22 reviews

La Casa del Sole del Sodo

ClaireRating, 5 stars7 months ago
We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!
Guest favorite
The exterior of the villa showcases a brick façade supported by wooden columns. A well-maintained lawn extends alongside the building, bordered by a rustic wooden fence. The serene landscape in the background highlights trees and open fields under a clear blue sky.
Villa in Montepulciano
4.91 out of 5 average rating, 121 reviews

Villa a Montepulciano con Piscina

LindaRating, 5 stars1 week ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Guest favorite
A private pool area is surrounded by lush greenery, featuring a clear blue pool with a lounge deck. Comfortable chairs are positioned nearby, accompanied by decorative pillows. Sun umbrellas provide shade, while vibrant flowers add a splash of color to the tranquil setting.
Villa in Passignano sul Trasimeno
4.9 out of 5 average rating, 30 reviews

Villa con piscina panoramica • Lago Trasimeno

LaurentRating, 5 stars8 months ago
Très très belle maison pleine de charme avec une superbe vue sur le lac. Hôtes très réactifs et proposant de nombreuses options bien appréciable. Au plaisir d’y revenir un jour !
Superhost
The image captures a serene villa surrounded by lush greenery, featuring a private pool and spacious garden. A stone pathway leads toward the villa, showcasing large windows and a shaded outdoor seating area, inviting guests to enjoy the tranquil landscape.
Villa in San Leo Bastia
4.92 out of 5 average rating, 12 reviews

Villa Elisa | Private Pool, Air/Co & Amazing View

Carlos Rating, 5 stars6 months ago
Villa Elisa is the best place I have stayed so far. Its construction style is old and special, the care of the Villa is down to the details, whether it is the exterior or interior, everything works is impressive even though some parts of the house are original from that time such as the doors, the windows, the floor tiles,The view is magnificent, magical whether with the radiant sun, under a torrential rain, under the clouds, under the mist or under the stars with the moon as a companion.Absolutely everything in detail and scrupulously organized, all thanks to its hosts Luciano and Christina. Now I will make an important section, if the Villa is majestic, they are also splendid and kind; I had the pleasure and pride of meeting them personally, people like few I have ever met and who are now scarce. Natural, simple and kind, always at hand unconditionally for whatever was needed.I recommend this place to everyone who wants to enjoy a great place and excellent company and 100 percent.
Superhost
The expansive garden features well-maintained grass and elegant trees casting shadows on the ground. In the background, the villa's rustic brick facade complements the natural surroundings, while additional greenery and an open sky create a serene atmosphere.
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars35 months ago
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Top guest favorite
An outdoor pool area is framed by an archway, featuring a clear blue pool surrounded by lounge chairs. Tall cypress trees and lush greenery rise in the background, complementing the serene, natural landscape.
Villa in Gaiole in Chianti
5 out of 5 average rating, 47 reviews

Sestuccia

RebeccaRating, 5 stars6 months ago
We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.
Superhost
A saltwater swimming pool is framed by lush greenery, with sunbeds positioned on the grass nearby. A natural fence enhances the privacy of the outdoor area, which is surrounded by trees that provide shade and a serene environment.
Villa in Pierle
4.88 out of 5 average rating, 26 reviews

Historic Villa Getaway with 6BR/9BA, Pool, Views

Alina-EmmaRating, 5 stars8 months ago
Wir waren mit einer Gruppe von zehn Personen in der Villa Pierle und hatten eine sehr schöne Zeit! Die Anfahrt an die Villa war zwar abenteuerlich, lohnte sich aber auf jeden Fall. Die Kommunikation mit Lizzy und Leo war super unkompliziert und wir haben uns gut aufgehoben gefühlt. Würden auf jeden Fall wieder kommen, dann aber mit Allrad-Autos!
Superhost
Villa in Bucine
5 out of 5 average rating, 9 reviews

Villa Tontenano Capannole Chianti private pool 7

AnthonyRating, 5 stars83 months ago
The villa was more beautiful in person than in the pictures. Margherita and her family were outstanding. Great location to visit many cities. I recommend using the train in bucinne rather than driving in the future. Walking around the vineyards and local farms was peaceful and relaxing The maintenance and facilities were better than expected

Villa rentals with a pool

Guest favorite
An aerial view captures the spacious villa with terracotta roofing and large windows. Surrounding olive trees and a lush garden frame a pristine pool area, featuring sun loungers and a covered dining space, inviting relaxation and outdoor gatherings.
Villa in Monte San Savino
5 out of 5 average rating, 7 reviews

Private villa with pool

BeatrizRating, 5 stars2 weeks ago
Los dueños son una pareja encantadora que nos atendieron muy bien, la casa preciosa, muy limpia, no pasamos nada de frío y no nos faltó de nada. Las vistas que se ven desde la casa son maravillosas!! Muy muy recomendable si queréis visitar la Toscana
Top guest favorite
The living area features a cozy seating arrangement with two armchairs and a yellow sofa. A brick archway frames the space, drawing attention to the traditional ceiling. A fireplace is situated in the corner, complemented by warm, earthy tones throughout the room.
Villa in Località Poggio Olivo
4.98 out of 5 average rating, 57 reviews

Beautiful villa with swimming pool in Tuscany

RoccoRating, 5 stars6 months ago
Our stay at the villa was absolutely incredible! The property (villa, surrounding grounds and the pool area) and the view were beautiful. The photos do not do it justice. it is exactly what you envision when thinking of a Tuscan villa. The house is large and clean, and it easily accommodated five adults with lots of extra room. The location is also very convenient, being close to a large grocery store and to the A1 highway. There are many restaurants and wineries nearby as well. Marco was a fantastic host who was very communicative and responsive. His parents (Ario and Santina), who live nearby, were lovely and friendly, while also giving us our space and privacy. Thank you very much Marco, Ario and Santina!!! We were sad to leave your beautiful villa and hope to be back soon!!
Guest favorite
A landscaped garden area is presented with green grass and a young tree, offering shade beneath a sunshade. A patio with wooden chairs provides a relaxed seating option, while scenic views of rolling hills and blue skies enhance the outdoor experience.
Villa in Rignano sull'Arno
4.89 out of 5 average rating, 55 reviews

VILLA with Pool - 3 Bedrooms (each with bathroom)

RitaRating, 5 stars6 days ago
Excelente espaço para desfrutar em família na região da Toscana. Casa super limpa e com todo equipamento para famílias grandes. Rápida comunicação com o interlocutor. Recomendamos!!
Guest favorite
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 39 reviews

Villa Il Sogno di Pietro, piscina privata e AC

ChanitahRating, 5 stars7 months ago
Het huis was prachtig. Bijna alles was geweldig een paar kleine puntjes. De keuken wat klein voor een grote groep. Er miste schaaltjes voor bijvoorbeeld yoghurt… of die hebben wij niet gevonden. Er was een stopcontact in een slaapkamer wat onveilig en er miste een douchegordijn in de gedeelde badkamer. Maar verder was het geweldig alles heel schoon en groot prachtige zwembad met tuin eromheen. Erg genoten
Superhost
Villa in Greve in Chianti
4.82 out of 5 average rating, 28 reviews

Romantic Villa with private pool and fabulous view

MenkoRating, 5 stars8 months ago
This an absolutely wonderful house with so many qualities inside as well as outside. Extremely well decorated and dreamy wonderful house inside, superb and beautiful views outside in a big and calming garden. Janine is fantastic, super friendly and extremely helpful. We forgot our passport and it was brought to Florence. This is just one example. Nothing to add, amazing to stay here.
Guest favorite
A private swimming pool is framed by lush greenery, with a gentle slope leading to the water's edge. Sunlight reflects off the clear water, creating a serene atmosphere. A tiled deck surrounds the pool, enhancing the tranquil setting.
Villa in Monte San Savino
4.99 out of 5 average rating, 69 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Tsz Kwan CarrieRating, 5 stars6 months ago
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.
Superhost
A spacious outdoor terrace features a large dining table surrounded by comfortable chairs, shaded by a large umbrella. Lush greenery and tall trees are visible in the background, creating a serene environment for al fresco dining.
Villa in Provincia di Siena
4.76 out of 5 average rating, 29 reviews

Villa Limone - 3 bedroom villa in Tuscany

AlessiaRating, 5 stars3 months ago
Bellissima e spaziosa casa. Tutto come da descrizione. Consigliato.
Top guest favorite
An outdoor space features a rectangular swimming pool surrounded by a stone patio. Sun loungers and a dining table with chairs are positioned under a large umbrella. Lush greenery and flowering plants enhance the scenic view of the hillside in the background.
Villa in Ortignano Raggiolo
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars6 months ago
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

Quick stats about villa rentals in Castiglion Fiorentino

  • Total rentals

    10 properties

  • Nightly prices starting at

    $110 before taxes and fees

  • Total number of reviews

    410 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

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