
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.

Exclusive 10 Acre Estate w/ Pool & Olive Grove!
Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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.

Relax e charme tra le colline del chianti
Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Torre dei Belforti
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.

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.

Countryside Dream farm in Tuscany
Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm in the middle of Tuscan Hills, you will be surrounded 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.

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.

Romantico appartamento nel borgo Toscano
La casa si trova in un antico borgo medioevale completamente ristrutturato pur mantenendo il fascino della sua storia. Nel borgo troverai due piscine, un ristorante, tanti giardini e molto altro... è in una posizione strategica per poter raggiungere le principali attrazioni come la Regione del Chianti, Firenze, Arezzo e Siena!
Popular amenities for Tuscany rentals with a pool
House rentals with a pool

Infinity pool in Chianti

Private Chianti Cottage, Garden & Vineyard Views

Cercis - La Palmierina

Casa Bada - Barn

Private villa/swimming pool in Tuscany

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

La Casa di Nada Home
Condo rentals with a pool

Charming old Tobacco Farm with Pool

Fattoria Lornano Winery- villa ''Trebbiano''

Scenic Stilish Country

💜 "Gaia" Podere Le Fontanelle

Farmhouse near Florence - Loggia

Residenza Vintage con Piscina nel Chianti

Ginestra: Private Pool Overlooking Florence

La Casetta
Home rentals with a private pool

Wp Relais Borgo Vignalunga

Villa Pergo is an ancient charming country villa

Esplora la natura al centro di Vigneti Chianti
Historic villa x8 with exclusive pool

Podere Molinaccio-Luxury Tuscan-style Eco Villa

Villa il Palagio nelle campagne toscane

Suite Casa Luigi con piscina esclusiva

Farmhouse , pool, 13 px. Lucca 10km
Destinations to explore
- Villa rentals Tuscany
- Condo rentals Tuscany
- Rentals with a washing machine and dryer Tuscany
- Fitness-friendly rentals Tuscany
- Bungalow rentals Tuscany
- Chalet rentals Tuscany
- Lakehouse rentals Tuscany
- Rentals with an accessible height toilet Tuscany
- Bed and breakfasts Tuscany
- Mansion rentals Tuscany
- Aparthotel rentals Tuscany
- Nature eco lodge rentals Tuscany
- Apartment rentals Tuscany
- Guesthouse rentals Tuscany
- Campsite rentals Tuscany
- Barn rentals Tuscany
- Rentals with beach access Tuscany
- Rentals with lake access Tuscany
- Earth house rentals Tuscany
- Smoking-friendly rentals Tuscany
- Cabin rentals Tuscany
- House rentals Tuscany
- Rentals with breakfast Tuscany
- Private suite rentals Tuscany
- Beach house rentals Tuscany
- Tent rentals Tuscany
- Holiday home rentals Tuscany
- Beachfront rentals Tuscany
- Rentals with a sauna Tuscany
- Cottage rentals Tuscany
- Rentals with a fire pit Tuscany
- Loft rentals Tuscany
- Pet-friendly rentals Tuscany
- Family-friendly rentals Tuscany
- Rentals with a fireplace Tuscany
- Rentals with outdoor seating Tuscany
- Rentals with a home theatre Tuscany
- Serviced apartment rentals Tuscany
- Boutique hotels Tuscany
- Farmstay rentals Tuscany
- Rentals with an EV charger Tuscany
- Tiny house rentals Tuscany
- Hostel rentals Tuscany
- Resort rentals Tuscany
- Waterfront rentals Tuscany
- Hotel rooms Tuscany
- Boat rentals Tuscany
- Rentals with a hot tub Tuscany
- Rentals with a patio Tuscany
- Ski-in/ski-out rentals Tuscany
- Rentals with a kayak Tuscany
- Luxury rentals Tuscany
- RV rentals Tuscany
- Townhouse rentals Tuscany
- Rentals with an accessible height bed Tuscany
- Castle rentals Tuscany
- Tower rentals Tuscany
- Rentals with a balcony Tuscany
- Rentals with pools Italy
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Art and culture Italy
- Wellness Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
- Entertainment Italy





