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Vacation rentals with a pool in Casentino

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Casentino

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost
Home in Anghiari
4.86 out of 5 average rating, 149 reviews

PoggiodoroLoft, Tuscan dream e relax

Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts: a beautiful fireplace that will keep the ambient warm in winter, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.

Superhost
A unique treehouse is highlighted among vibrant green grass adorned with clusters of purple flowers. Towering trees provide shade, and the structure features a deck that overlooks the surrounding natural landscape, inviting a sense of tranquility and harmony with nature.
Home in Florence
4.88 out of 5 average rating, 808 reviews

TREEhouse / casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.

Guest favorite
An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.
Home in Casale
4.88 out of 5 average rating, 189 reviews

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Top guest favorite
The rustic farmhouse is set against a clear blue sky, featuring a textured stone façade with wooden window shutters. A gravel courtyard is visible, adorned with potted plants and outdoor seating, offering a welcoming entrance to the tranquil countryside surroundings.
Farm stay in Reggello
4.97 out of 5 average rating, 176 reviews

Stone farmhouse, exclusive private pool

Podere Montebono is located on the hills of Reggello just 30 km from Florence. Ideal for reaching cities of art and naturalistic places. The farmhouse is isolated on a hill, surrounded by nature, olive trees, a garden and woods. The guest house is an independent wing of the large farmhouse on two floors: 3 double bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 5 people) We do not rent single rooms. Barbecue area. Total privacy.

Top guest favorite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 127 reviews

StageROOM03 - Idyllic Chianti cottage near Siena

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favorite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 140 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

Top guest favorite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 210 reviews

Il Castello di Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top guest favorite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favorite
A shared swimming pool is set in a grassy area, with clear blue water reflecting the sky. The surrounding landscape includes a stone building and lush greenery, while a wooden terrace with a trellis is positioned nearby, enhancing the serene country setting.
Home in Anghiari
4.99 out of 5 average rating, 255 reviews

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Italian Ground Coffee - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Top guest favorite
A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.
Farm stay in Arezzo
4.98 out of 5 average rating, 244 reviews

Esplora la natura al centro di Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Guest favorite
Farm stay in Castelfranco di sopra
4.88 out of 5 average rating, 309 reviews

Romantic apartment in the Tuscan village

The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

Top guest favorite
The outdoor pool features clear turquoise water, surrounded by a stone patio. Lush green hills and tall cypress trees create a scenic backdrop, while a few lounge chairs are positioned nearby for relaxation.
Home in Subbiano
4.99 out of 5 average rating, 91 reviews

Romantic cosy flat - Toscana Italy

Very quiet village, without shops but sometimes a baker, a haberdasher or a greengrocer come to the village and sell their products, as it used to be decades ago- nice experience! In front of the B&B you can see a small church from the end of the 1800s, with a bell tower. :)

Popular amenities for Casentino rentals with a pool

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