
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.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique 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.

Siena - apartment in the countryside near Siena
The Siena apartment for 5 people is located in the Santa Lucia farmhouse (DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is an apartment of about 100 square meters, located on the ground floor, consisting of three bedrooms (one double; one with two beds and one single), a large living room with fireplace, kitchen, two bathrooms with shower. Private outdoor gazebo with table and benches located in a private garden. AIR CONDITIONING in the rooms for a FEE according to consumption.

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.

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.

The Castle of 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.

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.

Romantic apartment in the Tuscan village
The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

Le Rondini - where it all began
We are on the main farm, the one where the farmers lived and the first to be recovered in Argenina. The outside loggia in the spring becomes home to some little friends who give it its name. We hung little baskets from the rafters all for them.

Borgo Ripostena – No. 8 Casa Vecchia
Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning.
Popular amenities for Siena rentals with a pool
House rentals with a pool

Italian Internal

Podere Scorno country house with swimming pool

Infinity pool in Chianti area

Cercis - La Palmierina

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Condo rentals with a pool

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Farmhouse near Florence - Loggia

Vintage Residence with Swimming Pool in Chianti

Ginestra: Private Pool Overlooking Florence

Poggiolieto Suite - on hills 10' from city center

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

Wp Relais Borgo Vignalunga

Villa Pergo is an ancient charming country villa

Explore nature in the heart of the Chianti vineyards
Historic villa x8 with exclusive pool

Agriturismo Henni panoramic pool sauna and jacuzzi

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $379 AUD | $412 AUD | $383 AUD | $359 AUD | $409 AUD | $486 AUD | $427 AUD | $376 AUD | $399 AUD | $373 AUD | $334 AUD | $338 AUD |
| 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 $101 AUD per night before taxes and fees

Verified guest reviews
Over 2,030 verified reviews to help you choose

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siena rentals

4.7 Average rating
Siena stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with a fire pit Siena
- Cottage rentals Siena
- Rentals with an EV charger Siena
- Rentals with breakfast Siena
- Boutique hotels Siena
- Holiday home rentals Siena
- Serviced apartment rentals Siena
- Family-friendly rentals Siena
- Pet-friendly rentals Siena
- Rentals with a fireplace Siena
- Bed and breakfasts Siena
- Rentals with a patio Siena
- Smoking-friendly rentals Siena
- Villa rentals Siena
- House rentals Siena
- Condo rentals Siena
- Rentals with a washing machine and dryer Siena
- Rentals with outdoor seating Siena
- Apartment rentals Siena
- Hotel rooms Siena
- Fitness-friendly rentals Siena
- Rentals with a hot tub Siena
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Mercato Centrale
- Parco Regionale Della Maremma
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Piazza della Repubblica
- Spiagge Bianche
- Del Chianti
- Piazzale Michelangelo
- Parco delle Cascine
- Pitti Palace
- Gulf of Baratti
- Palazzo Vecchio
- Boboli's Garden
- Piazza della Signoria
- Things to do Siena
- Art and culture Siena
- Nature and outdoors Siena
- Tours Siena
- Sightseeing Siena
- Food and drink Siena
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Nature and outdoors Siena
- Food and drink Siena
- Sports activities Siena
- Tours Siena
- 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







