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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 shimmering private pool reflects the clear sky, surrounded by a spacious garden with mature olive trees. The rustic stone building features a white wall and chimney, set against a backdrop of scattered clouds, enhancing the serene outdoor environment.
Trullo in Ceglie Messapica
4.95 out of 5 average rating, 133 reviews

Historic Villa and Trullo With a Private Pool

This villa and trullo from 1780, named trullo Fedele Bonotto, have been fully restored but still sit among the centuries-old olive trees of the area. Admire the historic stone walls, lounge in the private pool and solarium, and enjoy the beautiful garden area, all exclusive to guests and their privacy- The staff who takes care of the cleaning of the external and internal spaces of the property strictly follow the sanitary rules foreseen for Covid-19, before the arrival of each guest, full sanitation is carried out, the size of the house and the large garden absolutely guarantee the social security distances and contactless The villa, with centuries-old olive trees, has a dining area and fully equipped kitchen with utensils and crockery, dishwasher, fridge, oven. Thanks to a corridor you get to the two double bedrooms, each with its own bathroom. Detached from the villa, with separate entrance, you access the trullo, about 50 m2 large, where there is a double bed, a sofa / double bed and a private bathroom. In the outdoor area there is a large table with 10 chairs, several seats, a barbeque and the swimming pool for the exclusive use of guests. Also attached to the villa is the boiler room with laundry, complete with washing machine. The entire structure is for the exclusive use of guests who can live in this unforgettable moments of rest and tranquility! Guests have the exclusive use of the whole villa and of the attached trullo, and the entire outdoor area, which includes the living room, the swimming pool and the laundry. Immersed in the breathtaking countryside, the home is located close to the center of Ceglie Messapica. Dine at exceptional family-owned restaurants, browse through the local markets, and go for a hike or bike ride through the valleys. you have a park for your car, in 20 mintes you arrive on the Adriatic sea beaches, in 30 minutes you can arrive on the Ionico sea beaches.

Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 104 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
Home in Asciano
4.96 out of 5 average rating, 132 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
Home in Piancogno
5 out of 5 average rating, 41 reviews

Luxury Home private SPA with tub, sauna, and 180° view

✨ Sopra la Val Camonica ti aspetta una Luxury Home sospesa tra natura, design e vista 180°. Una villa intima per coppie e momenti speciali, dove la Private SPA esterna diventa il cuore del soggiorno: tinozza finlandese a 40°, sauna a legna, doccia calda e silenzio sotto le stelle ❤️ 🛏️ Suite king +soppalco matrimoniale 🛋️ Living panoramico vista valle 🍳 Cucina premium 📶 Fast Wi-Fi 🚗 Parcheggio privato+ricarica 🌿 Privacy, wellness e romanticismo. Un retreat da ricordare e vivere con calma.

Top guest favourite
Home in Bienno
4.99 out of 5 average rating, 166 reviews

Luxury Home + Private Spa, Jacuzzi, Sauna, and Alpine View

✨ La Quercia del Borgo è una dimora del ’700 nel cuore di Bienno, creata con amore per chi cerca fuga romantica, wellness e privacy. Pietra, legno e design avvolgono una SPA privata 24/7 con Jacuzzi, sauna finlandese e vista Alpi: un rituale intimo per anniversari,relax e momenti speciali❤️ 🛏️ Suite king con bagno privato+Smart TV 75’’ 🛋️ Salotto con divano letto memory 🍷 Cucina artigianale con cantinetta vini 🌄 Terrazze panoramiche 📶 Wi-Fi veloce e comfort premium ✨ Cura vera e passione❤️

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, 100 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.
Guest house in Macciano
4.97 out of 5 average rating, 227 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
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, 237 reviews

Tuscan charm of villa - countryside - Villa Senaia

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Top 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
4.97 out of 5 average rating, 109 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
The image shows a historic villa with a stone façade and a prominent tower. The property is surrounded by a well-kept lawn, with a clear pathway leading to the entrance. Lush greenery and decorative planters enhance the inviting appearance of the building.
Villa in Colombella
5 out of 5 average rating, 106 reviews

Torre Villa Belvedere Luxury & Relax with pool

"TORRE VILLA BELVEDERE" Meraviglioso appartamento di 260 metri quadrati , in Villa del XII sec .La piscina privata ( lunga 15 metri e larga 5 metri ) ,biliardo, freccette,ampio giardino , portico 80 mq, barbecue,palestra e area relax all'interno della Torre. Comodo parcheggio privato all'interno della struttura. Situato in posizione strategica ,12 Km da Perugia, 4km dalla superstrada,può ospitare comodamente fino a 8 ospiti 3 camere matrimoniali con bagno privato, Tv, cassaforte

Top guest favourite
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, 218 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
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, 97 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.

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