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Holiday rentals with a pool in Italy

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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
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5.0 out of 5 average rating, 218 reviews

Ancient Podere of the 1600s in Chianti in Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising exclusive services and experiences tailored to you. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you will find a saltwater swimming pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills and vineyards, with breathtaking sunsets.

Top Guest favourite
Villa in Colombella
5.0 out of 5 average rating, 114 reviews

Torre Villa Belvedere Luxury & Relax with pool

"TORRE VILLA BELVEDERE" A wonderful 260 square metre apartment in a villa with a 12th-century tower. It features a private swimming pool (15 metres long and 5 metres wide), billiards, darts, a large garden, an 80 square metre porch, a barbecue, a gym and a relaxation area inside the tower. Convenient private parking within the property. Located in a strategic position, 12 km from Perugia and 4 km from the motorway, it can comfortably accommodate up to 8 guests. It has 3 double bedrooms with private bathrooms, TV and a safe.

Top Guest favourite
Home in Bienno
4.99 out of 5 average rating, 184 reviews

Luxury Private SPA Residence with Jacuzzi, sauna and views of the Alps

✨ La Quercia del Borgo is a luxury home in the heart of Bienno: an 18th-century residence, stone and wood, warm design and a 24-hour private spa reserved just for you, with a jacuzzi, Finnish sauna and a view of the Alps. 🛏️ King suite + private bathroom 75”📺Smart TV Memory bed 🛋️ sofa 🍷 Artisanal cuisine and wine cellar + Welcome kit 🌄 Rooftop Fast 📶 Wi-Fi ❤️ A romantic getaway for anniversaries, proposals and honeymoons: privacy, charm and an authentic village, with every detail carefully prepared.

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 shaded pergola stands by a large swimming pool, draped with light curtains. Comfortable outdoor seating surrounds a circular table. Lush greenery and flowering plants create a serene backdrop, enhancing the tranquil atmosphere of the estate.
Villa in Guardea
4.99 out of 5 average rating, 103 reviews

Exclusive 10 Acre Estate w/ Pool & Olive Grove!

Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

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.
Guesthouse in Macciano
4.97 out of 5 average rating, 246 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.

Top Guest favourite
A serene outdoor pool is depicted, surrounded by lush greenery and overlooking a rolling hillside. The crystal-clear water reflects the blue sky, while a small dog stands at the pool's edge, enhancing the tranquil setting.
Cottage in Bellegra
4.94 out of 5 average rating, 526 reviews

The house among olive trees

A cottage made up of stone and timber built on two storeys, with a large living room, glass window, a couch for two people and a bathroom with sauna; on the second storey there is a double bedroom. Outdoors, there is a large garden with a porch equipped with BBQ and a wooden table. The site is located on the pleasant hills between Bellegra and Olevano Romano. We have currently added two beds, set up in a wonderful Indian teepe available for two extra guests in addition to the four ones.

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.

Guest favourite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 105 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Top Guest favourite
A trullo featuring traditional conical roofs is situated beside a rectangular swimming pool, surrounded by a manicured lawn. Olive trees create a natural border, while sun loungers are positioned around the pool area, inviting relaxation under a clear blue sky.
Trullo in Alberobello
4.98 out of 5 average rating, 106 reviews

Trulli Salamida, relax in Alberobello

In a bucolic atmosphere, framed by centuries-old olive trees, are the Trulli Salamida. Experience staying in the typical home of Alberobello, renovated respecting the historic architecture, with exposed stone rooms and equipped with every comfort for a unique and unforgettable vacation. You will be welcomed by the Salamida family, who have always been the guardians of the olive trees and producers of the inimitable Extra Virgin Olive Oil.

Top Guest favourite
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.

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