
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.

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.

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.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Spinosa Apartment in Podere Capraia
Two-room apartment on two floors, recently renovated with good taste furnishings: living room with sofa bed (1 and a half places), dining table, TV, WiFi. Kitchenette with oven, fridge and dishwasher. Bathroom with shower, toilet, and bidet. Upper floor, open attic double bedroom. Exit to equipped front patio. Heating (from 10/15 to 04/15), mosquito nets. Small and medium-sized pets allowed. Swimming pool (open from Jun. 1 to Sept. 30) shared with Solengo apartment

The Castle of 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.

Explore nature in the center of Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Simona’s house in the woods - Villa Boutique
Villa boutique immersa nel bosco all’interno del Parco dei Cimini alle pendici del Monte Cimino (800 m. s.l.m) L'immobile è grande circa 450mq ed è circondato da circa 1,5 ettari di giardino/pineta. La villa è dotata di una sauna e un hot tube a legna privata nel bosco. Una casa progettata da uno dei migliori architetti del centro Italia ed è sapientemente arredata.

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.
Popular amenities for Tuscany rentals with a pool
House rentals with a pool

Cercis - La Palmierina

Casa Bada - Barn

Explore Chianti from a Charming Stone House

Casetta Melograno – Cozy farmhouse in Chianti

Antico Borgo Ripostena – n. 8 Old House

House Rigomagno Siena

Casa Luigi Suite with exclusive pool

PoggiodoroLoft, Tuscan dream e relax
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Stone House in Chianti with pool and parking

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

Vintage apartment with swimming pool in Chianti

Ginestra: Private Pool Overlooking Florence

New, bright, cozy Florence apartment with view

Manuela apartment with pool in farmhouse
Home rentals with a private pool

Sole by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Podere Vignali by Interhome

Costacce by Interhome

Villa Pergo is an ancient charming country villa

Historic home with exclusive pool

Santa Margherita by Interhome

Villa il Palagio in the Tuscan countryside
Destinations to explore
- Villa rentals Tuscany
- Rentals with a washing machine and dryer Tuscany
- Condo rentals Tuscany
- Smoking-friendly rentals Tuscany
- Tent rentals Tuscany
- Lakehouse rentals Tuscany
- Fitness-friendly rentals Tuscany
- House rentals Tuscany
- Bungalow rentals Tuscany
- Private suite rentals Tuscany
- Pet-friendly rentals Tuscany
- Cabin rentals Tuscany
- Apartment rentals Tuscany
- Rentals with a patio Tuscany
- Campsite rentals Tuscany
- Rentals with breakfast Tuscany
- Bed and breakfasts Tuscany
- Mansion rentals Tuscany
- Earth house rentals Tuscany
- Barn rentals Tuscany
- Rentals with beach access Tuscany
- Rentals with lake access Tuscany
- Guesthouse rentals Tuscany
- Beachfront rentals Tuscany
- Rentals with a sauna Tuscany
- Rentals with a fire pit Tuscany
- Chalet rentals Tuscany
- Holiday home rentals Tuscany
- Cottage rentals Tuscany
- Aparthotel rentals Tuscany
- Loft rentals Tuscany
- Family-friendly rentals Tuscany
- Rentals with an accessible height toilet Tuscany
- Nature eco lodge rentals Tuscany
- RV rentals Tuscany
- Hostel rentals Tuscany
- Rentals with outdoor seating Tuscany
- Tiny house rentals Tuscany
- Waterfront rentals Tuscany
- Rentals with an EV charger Tuscany
- Rentals with a kayak Tuscany
- Townhouse rentals Tuscany
- Ski-in/ski-out rentals Tuscany
- Rentals with a fireplace Tuscany
- Tower rentals Tuscany
- Rentals with an accessible height bed Tuscany
- Castle rentals Tuscany
- Hotel rooms Tuscany
- Luxury rentals Tuscany
- Boutique hotels Tuscany
- Farmstay rentals Tuscany
- Rentals with a balcony Tuscany
- Boat rentals Tuscany
- Rentals with a hot tub Tuscany
- Serviced apartment rentals Tuscany
- Rentals with a home theatre Tuscany
- Beach house rentals Tuscany
- Resort rentals Tuscany
- Rentals with pools Italy
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Entertainment Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Art and culture Italy
- Nature and outdoors Italy
- Wellness Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
- Entertainment Italy




