
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.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

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.

Pieve di Caminino Historic Farm
Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

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.

Stone House with Exclusive Pool Codilungo in Chianti
Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Il Castello di Ferrano - Castle in Tuscany
Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)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.

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.

Countryhouse 9 km to Florence-2+1g,free park, wine
We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
Popular amenities for Tuscany rentals with a pool
House rentals with a pool

Cottage surrounded by nature

Ancient Barn in Chianti with Pool

Casa Bada - Barn

“il colle” nice house surrounded by vineyard

Private villa/swimming pool in Tuscany

Luxury Villa with a fantastic view

Casa Luigi Suite with exclusive pool

House Rigomagno Siena
Apartment rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Chianti La Pruneta, Michelangelo apartment.

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Swimming Pool in Chianti
Home rentals with a private pool

Costacce by Interhome

Esplora la natura al centro di Vigneti Chianti

Historic home with exclusive pool

Aurora by Interhome

Charming villa in the Chianti hills

Villa il Palagio in the Tuscan countryside

Il Pezzo Farm by Interhome
Wp Relais Villa Vignalunga
Destinations to explore
- Aparthotel rentals Tuscany
- Apartment rentals Tuscany
- Chalet rentals Tuscany
- Waterfront rentals Tuscany
- Bungalow rentals Tuscany
- Fitness-friendly rentals Tuscany
- Rentals with breakfast Tuscany
- Campsite rentals Tuscany
- Rentals with an accessible-height toilet Tuscany
- Earth house rentals Tuscany
- Holiday home rentals Tuscany
- Tiny house rentals Tuscany
- Guest house rentals Tuscany
- Rentals with a washing machine and dryer Tuscany
- Beach house rentals Tuscany
- Motorhome rentals Tuscany
- Tower rentals Tuscany
- Hostel rentals Tuscany
- Townhouse rentals Tuscany
- Beachfront rentals Tuscany
- Rentals with a sauna Tuscany
- Private suite rentals Tuscany
- Tent rentals Tuscany
- Family-friendly rentals Tuscany
- Resort rentals Tuscany
- Rentals with a balcony Tuscany
- Hotel rooms Tuscany
- Rentals with a fireplace Tuscany
- Boat rentals Tuscany
- Rentals with a hot tub Tuscany
- Loft rentals Tuscany
- Rentals with a kayak Tuscany
- Villa rentals Tuscany
- Smoking-friendly rentals Tuscany
- Barn rentals Tuscany
- Rentals with beach access Tuscany
- Rentals with lake access Tuscany
- Rentals with an accessible-height bed Tuscany
- Castle rentals Tuscany
- Bed and breakfasts Tuscany
- Mansion rentals Tuscany
- Flat rentals Tuscany
- Nature eco lodge rentals Tuscany
- Pet-friendly rentals Tuscany
- Boutique hotels Tuscany
- Farm stay rentals Tuscany
- Rentals with a cinema Tuscany
- Rentals with an EV charger Tuscany
- Cottage rentals Tuscany
- Serviced apartment rentals Tuscany
- Rentals with a patio Tuscany
- Cabin rentals Tuscany
- Luxury rentals Tuscany
- Rentals with outdoor seating Tuscany
- Lakehouse rentals Tuscany
- Ski-in/ski-out rentals Tuscany
- House rentals Tuscany
- Rentals with a firepit Tuscany
- Rentals with pools Italy
- Things to do Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Art and culture Tuscany
- Things to do Italy
- Sports activities Italy
- Food and drink Italy
- Wellness Italy
- Nature and outdoors Italy
- Art and culture Italy
- Tours Italy
- Entertainment Italy
- Sightseeing Italy




