
Holiday rentals with a pool in Tuscany
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Tuscany
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 143 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
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. 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'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
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, 250 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
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.
4.99 out of 5 average rating, 116 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
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.
4.99 out of 5 average rating, 227 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
Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.
4.99 out of 5 average rating, 516 reviews
Frontemare house with exclusive sea access
Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.
4.95 out of 5 average rating, 111 reviewsPopular amenities for Tuscany rentals with a pool
House rentals with a pool

Conca d'Oro villa with private pool, sleeps 4
4.92 out of 5 average rating, 173 reviews
Relaxation and charm in the Chianti hills
4.99 out of 5 average rating, 114 reviews
PoggiodoroLoft, Tuscan dream e relax
4.87 out of 5 average rating, 167 reviews
Open space surrounded by nature
4.96 out of 5 average rating, 137 reviews
Cottage surrounded by nature
4.99 out of 5 average rating, 111 reviews
Casa Giulia di Sopra Farmhouse
4.95 out of 5 average rating, 106 reviews
Palazzo Monaci - Pool in the Crete Senesi
4.96 out of 5 average rating, 142 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
4.98 out of 5 average rating, 145 reviewsApartment rentals with a pool

La Casetta
4.93 out of 5 average rating, 197 reviews
Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
4.97 out of 5 average rating, 151 reviews
Bel Canto Lari, exclusive, rural, Tuscan retreat
4.97 out of 5 average rating, 105 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Relax Among the Chianti Vineyards - IlVillinoFarmhouse
4.81 out of 5 average rating, 365 reviews
Poggiolieto Suite - on hills 10' from city center
4.83 out of 5 average rating, 228 reviews
Romantic Residence with Swimming Pool in Chianti
5.0 out of 5 average rating, 128 reviewsHome rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
Farmhouse , pool, 13 px. Lucca 10km
4.99 out of 5 average rating, 148 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 122 reviews
TREEhouse / casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Explore nature in the center of Vigneti Chianti
4.97 out of 5 average rating, 265 reviews
Magnificent Tuscan Villa, amazing interiors & view
5.0 out of 5 average rating, 16 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviews
Agriturismo Henni panoramic pool sauna and jacuzzi
4.94 out of 5 average rating, 51 reviewsDestinations to explore
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