
Holiday rentals with a pool in Siena
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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 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.

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.

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!

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.

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.

La Casa di Nada - Suite
From every window of my home there are wonderful views of the Tuscan hills, a charm that will accompany every moment of your stay. My kitchen is fully equipped and the rooms are comfortable and bright, with a private bathroom for each room. In the living room I have a beautiful fireplace all for you. A practical laundry completes this refuge in the Heart of Chianti
Popular amenities for Siena rentals with a pool
House rentals with a pool

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

House “il colle”.nice house surrounded by vineyard

Private villa/swimming pool in Tuscany

Charming estate with views

Antico Borgo Ripostena – n. 8 Old House

Casa di Lyndall - Entire house with exclusive pool

Gaiole in Chianti Poggio Casabianca
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Agriturismo La Farneta: The Linden Trees Apartment

Stone House in Chianti with pool

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

House between Firenze, Arezzo, chianti e Siena

Vintage apartment with swimming pool in Chianti

Manuela apartment with pool in farmhouse
Home rentals with a private pool

Poggio Cuccule by Interhome

Sole by Interhome

Podere Vignali by Interhome

Casa Clotilde by Interhome

Historic home with exclusive pool

Organic Wellness Oasis by Interhome

The Leccio by Interhome

Podere San Lorenzo by Interhome
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $274 NZD | $247 NZD | $385 NZD | $438 NZD | $499 NZD | $593 NZD | $521 NZD | $459 NZD | $487 NZD | $432 NZD | $334 NZD | $279 NZD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Quick stats about holiday rentals with a pool in Siena

Total holiday rentals
Explore 90 holiday rentals in Siena

Nightly prices starting at
Siena holiday rentals start at $88 NZD per night before taxes and fees

Verified guest reviews
Over 1,970 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Siena holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Siena rentals

4.7 Average rating
Siena stays receive an average rating of 4.7 out of 5 from guests
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