
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.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Podere La Castellina - No. 2 LECCETO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

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.

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

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.

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.

Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

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

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.

TUSCANY farm house SWIMMING POOL
Our little farm is a beautiful location for a relaxing vacation with a private swimming pool( open around the 10th of May) We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

La Pieve - the house next to the church
To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?
Popular amenities for Siena rentals with a pool
House rentals with a pool

Italian Internal

Podere Scorno country house with swimming pool

Wonderful country house

Ancient Barn in Chianti with Pool

Private Cottage with Plunge Pool in Tuscan Estate

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Leonardo - Chianti/Siena, Florence, San Gimignano.
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Casa Biancospino Crete Senesi | Podere Fossaccio

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Manuela apartment with pool in farmhouse
Other holiday rentals with a pool

S.Ilaria - Private pool Villa with 2 bedrooms

Apt 4: Montepulciano 800 yr old Monastery

Family Forest - Pool in the Crete Senesi

Large Apartment in a Villa, swimming pool, Siena

Country Charm & Jacuzzi

Tuja

Very cosy cottage with beautiful views

Suite in the nature between Siena and Grosseto
Destinations to explore
- Private suite rentals Siena
- Loft rentals Siena
- Farm stay rentals Siena
- Rentals with an accessible-height bed Siena
- Rentals with breakfast Siena
- Rentals with outdoor seating Siena
- Flat rentals Siena
- Rentals with a hot tub Siena
- Villa rentals Siena
- Rentals with an EV charger Siena
- Rentals with a fireplace Siena
- Rentals with a patio Siena
- House rentals Siena
- Tent rentals Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Luxury rentals Siena
- Nature eco lodge rentals Siena
- Townhouse rentals Siena
- Hotel rooms Siena
- Rentals with a balcony Siena
- Barn rentals Siena
- Guest house rentals Siena
- Rentals with a cinema Siena
- Tiny house rentals Siena
- Rentals with a firepit Siena
- Rentals with lake access Siena
- Family-friendly rentals Siena
- Rentals with a washing machine and dryer Siena
- Serviced apartment rentals Siena
- Castle rentals Siena
- Apartment rentals Siena
- Rentals with beach access Siena
- Cottage rentals Siena
- Bed and breakfasts Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Smoking-friendly rentals Siena
- Rentals with a sauna Siena
- Boutique hotels Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Mugello Circuit
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Parco delle Cascine
- Medici Chapel
- Basilica of Santa Croce
- Piazza della Signoria
- Del Chianti
- Stadio Artemio Franchi
- Things to do Siena
- Nature and outdoors Siena
- Sports activities Siena
- Tours Siena
- Sightseeing Siena
- Art and culture Siena
- Food and drink Siena
- Things to do Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Food and drink Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Wellness Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Things to do Italy
- Food and drink Italy
- Sightseeing Italy
- Entertainment Italy
- Wellness Italy
- Art and culture Italy
- Sports activities Italy
- Nature and outdoors Italy
- Tours Italy





