
Vacation 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.

Podere Vergianoni immerso nelChianti con piscina
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.

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.

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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

Tuscan countryside, peace and relaxation 10 minutes from Siena
Our accommodation is close to Siena, therefore to nightlife, the city center but also to the small airport of Ampugnano, parks, and public transport. You'll love our place for its light, the comfort of the bed, the kitchen, the intimacy, and the high ceilings. Our apartment is suitable for couples, solo adventurers, business travelers, families (with children) and furry friends (pets).

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.

Explore Chianti from a Charming Stone House
Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.
Popular amenities for Siena rentals with a pool
House rentals with a pool

Infinity pool in Chianti area

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Casa Bada - Barn

Private villa/swimming pool in Tuscany

The Owl: view, pool and garden

Leonardo - Chianti/Siena, Firenze, San Gimignano.

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

Chianti La Pruneta, Michelangelo apartment.

Traditional Apartment with Patio and Garden View

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

Agriturismo La Farneta: The Linden Trees Apartment

Stone House in Chianti with pool

Adalberto Apartment inside the Manor of Fulignano

VILLA LE PERGOLE - Florence

House between Firenze, Arezzo, chianti e Siena
Home rentals with a private pool

Sole by Interhome

Ambrogetta by Interhome.

La Felcaia by Interhome

Podere Vignali by Interhome

Melograno by Interhome

Historic home with exclusive pool

Podere San Lorenzo by Interhome

Charming villa in the Chianti hills
Quick stats about vacation rentals with a pool in Siena
Total rentals
90 properties
Nightly prices starting at
R870 ZAR before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Provence Vacation rentals
- Rome Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Venice Vacation rentals
- Florence Vacation rentals
- Naples Vacation rentals
- Francavilla al Mare Vacation rentals
- Marseille Vacation rentals
- Cannes Vacation rentals
- Italian Riviera Vacation rentals
- Bologna Vacation rentals
- Serviced apartment rentals Siena
- Family-friendly rentals Siena
- Rentals with a patio Siena
- Rentals with a fire pit Siena
- Rentals with an EV charger Siena
- Rentals with outdoor seating Siena
- Smoking-friendly rentals Siena
- Villa rentals Siena
- Rentals with breakfast Siena
- Apartment rentals Siena
- Bed and breakfasts Siena
- Rentals with a washer and dryer Siena
- Boutique hotel rentals Siena
- Cottage rentals Siena
- Rentals with a fireplace Siena
- Condo rentals Siena
- Rentals with a hot tub Siena
- Hotel rentals Siena
- Pet-friendly rentals Siena
- Fitness-friendly rentals Siena
- Vacation home rentals Siena
- House rentals Siena
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Cala Violina
- Gulf of Baratti
- Uffizi Gallery
- Mugello Circuit
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Spiagge bianche
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Kite Beach Fiumara
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Things to do Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Food and drink Siena
- Art and culture Siena
- Tours Siena
- Things to do Siena
- Tours Siena
- Art and culture Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Food and drink Siena
- Things to do Tuscany
- Sightseeing Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Wellness Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Things to do Italy
- Entertainment Italy
- Food and drink Italy
- Wellness Italy
- Tours Italy
- Nature and outdoors Italy
- Sports activities Italy
- Art and culture Italy
- Sightseeing Italy