
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.

Infinity view
Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

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.

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.

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.

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.

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.

Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

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.

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.
Popular amenities for Tuscany rentals with a pool
House rentals with a pool

Cottage surrounded by nature

Private villa/swimming pool in Tuscany

Casa San Ripa: Relax Oasis with Private Pool

Relaxation and charm in the Chianti hills

Villa of the Hydrangeas

Nada Home

Antico Borgo Ripostena – n. 8 Old House

Romantic cosy flat - Toscana Italy
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Farmhouse near Florence - Torretta

Charming old Tobacco Farm with Pool

Scenic Stilish Country

💜 "Gaia" at Podere Le Fontanelle

Vintage Residence with Pool in Chianti

Ginestra: Private Pool Overlooking Florence
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa
Historic villa x8 with exclusive pool

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Farmhouse , pool, 13 px. Lucca 10km

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





