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Holiday 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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Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 111 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Guest favourite
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, 200 reviews

Infinity view

Completely renovated location with breathtaking views of the Valdarno. The ground floor consists of a living room with two windows overlooking the patio, fireplace, sofa bed, bathroom with large shower and modern kitchen with steel island, with three French windows to access the outdoor dining area with BBQ. The second floor consists of two double bedrooms each with its own bathroom with shower. The garden is well-kept, there are various relaxation corners, a sundeck and an infinity pool with hydrolysis

Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.9 out of 5 average rating, 240 reviews

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Top Guest favourite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino
4.99 out of 5 average rating, 113 reviews

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

Top Guest favourite
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, 192 reviews

Stone farmhouse, exclusive private pool

Podere Montebono is located in the hills of Reggello, just 30 km from Florence. Ideal for getting to cities of art and natural sites. The farmhouse is secluded on a hill, immersed in nature, surrounded by olive trees, a garden and woods. The guest house is a separate wing of the large two-storey farmhouse: 3 bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. Barbecue area. Total privacy.

Superhost
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, 225 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). 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 favourite
The exterior of the villa is showcased, featuring stone walls and greenery. A spacious stone patio is visible, furnished with a dining table and chairs, surrounded by neatly trimmed bushes and potted plants, creating an inviting space for outdoor gatherings.
Farm stay in Loro Ciuffenna
4.99 out of 5 average rating, 123 reviews

Il Roseto: your Villa in Tuscan Countryside

In the heart of Tuscany between Arezzo, Florence and Siena but far away from the bustle of the cities, you will find a pristine landscape where to enjoy nature and relaxing, amazing views and much more for a perfect getaway with your friends or family. A villa of 190 mq with 600 mq garden,where you can enjoy lunch outdoors, have fun making pizza and baking it in the wood- oven, or savour a wonderful barbeque. A comfortable Villa for guests who love being together.

Top Guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Guest favourite
An aerial view of the CasaMacchia property, showcasing a traditional stone villa surrounded by lush greenery and mature trees. A private pool is visible within the garden, complemented by terraced areas and colorful flowers. The landscape features rolling hills in the background.
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 100 reviews

Casa Macchia /Florence charming villa private Pool

Casa Macchia (over 200m²): Historic Tuscan country house in a natural setting with magical views and tranquillity. Ideal for families and groups: 9 beds plus 3 children's beds and 1 toddler bed offer plenty of space and places to retreat. Highlights: Large pool, very well-equipped kitchen & outdoor kitchen (table for 10). Remodelled by the designer Willy Fleckhaus and used by a family. 12 hectares of private land guarantee absolute privacy.

Superhost
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 219 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Top Guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari
4.99 out of 5 average rating, 271 reviews

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - 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.

Guest favourite
Farm stay in Castelfranco di sopra
4.89 out of 5 average rating, 338 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!

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