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Holiday rentals with a pool in Italy

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Italy

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

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Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 207 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Guest favourite
The illuminated salt water pool is surrounded by two large umbrellas, providing shade, and deck chairs are neatly arranged nearby. The scene is set against a twilight sky with distant mountains visible, creating a serene outdoor space for relaxation.
Home in Pescia
5 out of 5 average rating, 14 reviews

Tuscan dream home with pool !

La Capanna: A 1800s Tuscan barn reborn in 2020 as a chic holiday retreat, beckoning your family. Enjoy stunning valley vistas, a 9x4 salt water pool, olive grove, and alfresco kitchen. Inside, discover luminous spaces blending modernity with Tuscan tradition. Our wabi sabi aesthetic embraces neutral tones and natural elements—wood, stone, raffia, and linen—harmonizing old-world charm with contemporary comfort. This is our cherished home; consider yourself fortunate to experience its magic.

Top guest favourite
Loft in Balestrate
5 out of 5 average rating, 176 reviews

Countryside Excape - Luxury Sicilian Loft & Pool

Indulge in a refined Sicilian escape in a luxury loft with a private pool, set within the historic Baglio Cappello, a traditional Sicilian courtyard farmhouse surrounded by unspoiled countryside. A place where time slows down, offering absolute privacy, quiet elegance and authentic charm. Perfectly located between Palermo and Trapani, it is an intimate retreat for couples and families seeking comfort, exclusivity and a truly authentic luxury experience. Car required.

Top guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano
4.95 out of 5 average rating, 154 reviews

A paradise in Montepulciano...

Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY.

Top guest favourite
Flat in Cerreto di Molo
4.98 out of 5 average rating, 180 reviews

Infinity

Typical Piedmontese farmhouse immersed in the greenery of Val Borbera, 8 km from the A7 exit Vignole Borbera tollbooth, consisting of a large living room with kitchenette, bedroom with private bathroom, mezzanine with double bed and bathroom. Sofa bed in the living room. In total sleeps 6 Totally fenced 6000-meter garden with 12x6 infinity pool The pool is not exclusive Possibility to use a Weber barbecue Wall box

Top guest favourite
A private terrace is showcased with wooden beams and climbing plants, offering views of the surrounding hills. A vintage trunk is positioned under the shelter, and greenery fills the space, providing a serene natural setting.
Farm stay in Barga
4.89 out of 5 average rating, 141 reviews

Al Benefizio Agritourism - "La Stalla" Apartment

Private self-catering apartment with private terrace, in a historic rural farmhouse surrounded by the greenery of Tuscany, swimming pool and panoramic views of the village of Barga, 2.5 km away. At our Agritourism, we also offer private cooking lessons and beekeeping lessons with a tasting of our honeys. Here you can buy our honey and different types of local food and wine products.

Guest favourite
The stone cottage is set amidst lush greenery, featuring a sloped roof and a large glass door that opens onto a sunlit terrace. Sun loungers are positioned nearby, surrounded by flowering plants, with olive trees visible in the background against a clear blue sky.
Farm stay in Cavriglia
4.92 out of 5 average rating, 355 reviews

Chianti La Pruneta, Raphael Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

Top guest favourite
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.

Top guest favourite
A two-story southern Italian villa is set amidst a lush garden, featuring green trees and shrubs. The facade showcases wooden shuttered windows and a pathway leading to the entrance. A sense of tranquility emanates from the rustic surroundings.
Villa in Badolato
4.98 out of 5 average rating, 132 reviews

Winery house with pool and amazing view

The house is an old southern Italian villa, located in a rural area next to Badolato’s old village. The location is still used as a winery by our family. You will appreciate the wonderful view of the medieval village, the Ionian Sea, the surrounding vineyards, while also experiencing the authentic southern Italian lifestyle.

Top guest favourite
A rustic cottage with a stone facade is set against a backdrop of rolling hills and a dramatic sunset sky. Surrounding greenery includes manicured shrubs and olive trees. A red umbrella stands at the entrance, providing a spot of color against the serene landscape.
Farm stay in Pierantonio
4.97 out of 5 average rating, 115 reviews

La Stalla - San Gabriel House

1 bedroom cottage located on the property of Casa San Gabriel, set in the stunning Umbrian countryside, it has access to the large gardens and swimming pool. The cottage is a full self catering studio cottage with 1 double or twin bed and air-conditioning.

Guest favourite
A spacious terrace features four wicker chairs and a glass table, surrounded by lush greenery. The coastline and sea are visible in the background, framed by an arched opening, creating a serene outdoor seating area.
Home in Praiano
4.84 out of 5 average rating, 100 reviews

Seaside Villa Positano

A really amazing position front of the see. All the rooms have windows with panorama to the Amalfy Coast. The stile of the villas is modern and antique, typically of the Positanos houses. Tree bedrooms, tree bathrooms, terraces, garden with pool.

Guest favourite
A large swimming pool is set amidst lush greenery, featuring a terracotta border. The pool reflects the clear blue sky, and gentle hills can be seen in the background, offering a peaceful view of the surrounding landscape.
Home in Figline Valdarno
4.94 out of 5 average rating, 119 reviews

The Owl: view, pool and garden

The farmhouse apartment ‘The Owl’ is placed on the hills of Chianti, between Florence, Siena and Arezzo, and it’s an ideal place for a different holiday and stay in Tuscany, with its location in a landscape, which invites you to fully relax.

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