
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.

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.

House between Firenze, Arezzo, chianti e Siena
The House is located in a restored medieval village. There is an atmosphere of peace and tranquility, the gardens are full of flowers and aromatic plants and there is a beautiful panoramic view of the Arno Valley. There is a private terrace outside and two swimming pools to share with other appartraments. Perfect for relaxing and for reaching the main attractions like Florence, Siena, Arezzo, Chianti, Sangimignano. Here you will live a unique experience in the heart of Tuscany ...

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.

Il Castello di 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.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

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

Vineyards Paradise

Ancient Barn in Chianti with Pool

Il Vecchio Mulino

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Collina Power

Antico Borgo Ripostena – n. 8 Old House

Luxury Villa with a fantastic view
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Vintage Residence with Swimming Pool in Chianti

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

Wp Relais Borgo Vignalunga

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa

Esplora la natura al centro di Vigneti Chianti

Historic home with exclusive pool

Charming villa in the Chianti hills

Villa il Palagio in the Tuscan countryside

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




