
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.

Private spa in a historic residence overlooking the Alps
✨ Jacuzzi, Finnish sauna and views of the Alps: in Bienno, La Quercia del Borgo is an 18th-century residence with a 24-hour private spa all for you. Natural stone, warm light and a sense of well-being create a romantic retreat above the rooftops of the village and the mountains. 🛏️ King suite with private bathroom and 75" Smart TV 🛁 Service bathroom Memory bed 🛋️ sofa 🍷 Artisanal cuisine, wine cellar and welcome kit 🌄 Rooftop Fast 📶 Wi-Fi ❤️ For couples, anniversaries, proposals and honeymoons: privacy, ambience and care
4.99 out of 5 average rating, 189 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
4.9 out of 5 average rating, 241 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
4.99 out of 5 average rating, 105 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.
4.97 out of 5 average rating, 251 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 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.
4.96 out of 5 average rating, 116 reviews
Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
4.98 out of 5 average rating, 127 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
5.0 out of 5 average rating, 352 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.
4.98 out of 5 average rating, 107 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.
4.99 out of 5 average rating, 481 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.
4.98 out of 5 average rating, 107 reviews
Simona’s house in the woods - Villa Boutique
Boutique villa nestled in the woods inside the Cimini Park on the slopes of Mount Cimino (800 m above sea level) The property is about 450 sqm and is surrounded by about 1.5 hectares of garden/pine forest. The villa is equipped with a sauna and a private wood-burning hot tub in the woods. A house designed by one of the best architects in central Italy and is expertly furnished.
4.98 out of 5 average rating, 133 reviewsPopular amenities for Italy rentals with a pool
House rentals with a pool

Frontemare house with exclusive sea access
4.95 out of 5 average rating, 111 reviews
VillaGió swimming pool Nordic bath sauna exclusive use
4.95 out of 5 average rating, 128 reviews
Hilltop Views From a Historic Tuscan Home
4.99 out of 5 average rating, 110 reviews
CASA GALLO ROSSO Hills & Panorama
4.97 out of 5 average rating, 106 reviews
Cercis - La Palmierina
4.96 out of 5 average rating, 146 reviews
Borgo Ripostena – No. 8 Casa Vecchia
4.95 out of 5 average rating, 201 reviews
La Vigna Vacation Home with Pool
4.89 out of 5 average rating, 212 reviews
Belfortilandia, the rustic cottage
4.96 out of 5 average rating, 127 reviewsCondo rentals with a pool

The Painter's House
4.99 out of 5 average rating, 335 reviews
Resort Style Apartment with Lake Views
4.94 out of 5 average rating, 430 reviews
Iris Two-Room Apartment - Fior di Lavanda Residence
4.98 out of 5 average rating, 115 reviews
"Biancospino" Bed & Wine Farmhouse
4.99 out of 5 average rating, 171 reviews
carpe diem
4.88 out of 5 average rating, 134 reviews
Pampering in the Mountains
4.98 out of 5 average rating, 151 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Apartment 10 minutes Vatican + pool&parking
4.92 out of 5 average rating, 174 reviewsHome rentals with a private pool

Farmhouse , pool, 13 px. Lucca 10km
4.99 out of 5 average rating, 148 reviews
Trullo Apulia: swimming pool, jacuzzi & steam room
4.92 out of 5 average rating, 203 reviews
Sicily Authentic Vibration Eighteenth-Century Farm with Panoramic Sea Views
4.96 out of 5 average rating, 106 reviews
Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
TREEhouse / casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Sprawling Coastal Views From a Villa with a Pool
4.92 out of 5 average rating, 191 reviewsPrivate swimming pool and sauna surrounded by nature and Lake Como
4.95 out of 5 average rating, 232 reviews
Historic Villa and Trullo With a Private Pool
4.96 out of 5 average rating, 139 reviewsDestinations to explore
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