
Holiday rentals with a pool in Siena
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Siena
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

Tuscan charm of villa - countryside
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

StageROOM03 - Idyllic Chianti cottage near Siena
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.

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.

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.

Siena Country Loft Hideway
Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Poggio dell'orso.Traditional Casale. Amazing views
Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

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.
Popular amenities for Siena rentals with a pool
House rentals with a pool

Italian Interior

Cozy country house Podere Scorno with pool

Villa Casabella near Siena

Ancient Barn in Chianti with Pool

La Lisa: country house surrounded by fields

Charming estate with views

Antico Borgo Ripostena – n. 8 Old House

Casa di Lyndall - Entire house with exclusive pool
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Traditional Apartment with Patio and Garden View

Cottage 48 sqm, swimming pool, relaxation, surrounded by greenery

Agriturismo La Farneta: The Linden Trees Apartment

La Foresteria | Granary House

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa
Home rentals with a private pool

Poggio Cuccule by Interhome

La Felcaia by Interhome

Podere Vignali by Interhome

Organic Wellness Oasis by Interhome

Podere San Lorenzo by Interhome

Casa Frati by Interhome
Wp Relais Villa Vignalunga

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool
Destinations to explore
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Rentals with outdoor seating Siena
- Rentals with a firepit Siena
- Rentals with a washing machine and dryer Siena
- Tiny house rentals Siena
- Rentals with beach access Siena
- Townhouse rentals Siena
- Rentals with a balcony Siena
- Guest house rentals Siena
- Tent rentals Siena
- Rentals with a hot tub Siena
- Bed and breakfasts Siena
- Nature eco lodge rentals Siena
- House rentals Siena
- Castle rentals Siena
- Apartment rentals Siena
- Rentals with an accessible-height bed Siena
- Farm stay rentals Siena
- Rentals with a cinema Siena
- Family-friendly rentals Siena
- Rentals with an EV charger Siena
- Hotel rooms Siena
- Villa rentals Siena
- Barn rentals Siena
- Loft rentals Siena
- Flat rentals Siena
- Serviced apartment rentals Siena
- Rentals with breakfast Siena
- Rentals with lake access Siena
- Smoking-friendly rentals Siena
- Rentals with a patio Siena
- Rentals with a fireplace Siena
- Cottage rentals Siena
- Luxury rentals Siena
- Rentals with a sauna Siena
- Private suite rentals Siena
- Boutique hotels Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Kite Beach Fiumara
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Spiaggia Marina di Cecina
- Mugello Circuit
- Palazzo Vecchio
- Cala Di Forno
- Stadio Artemio Franchi
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Tours Siena
- Nature and outdoors Siena
- Sports activities Siena
- Food and drink Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Wellness Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Things to do Italy
- Nature and outdoors Italy
- Sightseeing Italy
- Sports activities Italy
- Wellness Italy
- Tours Italy
- Entertainment Italy
- Art and culture Italy
- Food and drink Italy




