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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.

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Home in Montespertoli

4.84 out of 5 average rating, 69 reviews

Holiday immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a vacation immersed in the Tuscan countryside, with a large equipped pool 🌞💐The scents of nature, the breathtaking landscapes and the swimming pool will be the setting for the relaxation you are looking for. 🚴🏻‍♂️🏃‍♀️Then if you feel the need to move around you can swim, walk, or run through the trails around your country home. 🏛The strategic location of the apartment allows you to hike in Florence, Siena and Pisa. ✨The apartments are recently renovated in Tuscan style.”

Condo in CORTONA

4.96 out of 5 average rating, 24 reviews

Relaxation and peace in the countryside Cortona G

"Le Oche Grigie" was the first Charming Home in Cortona totally dedicated to people in love. Unlike other lodgin we only accept couples without children. This means for our guests memorable romantic experiences, emotions and complicity in a country house, away from the distractions of daily life. Strategically positioned in the center of an area of extraordinary beauty, only 3 exclusive and independent apartments, renovated with fine finishing and natural materials. Garden and swimming pool.

Condo in Soiana

4.98 out of 5 average rating, 45 reviews

Charming apartment with garden, pool and valley view

Apartment in Historical building with shared garden and pool. The property is located in a typical Medieval Tuscan village close to Terricciola (PI) which is part of the wine route. The historic palazzo was built in the 17th Century and has been converted into several individual apartments sharing a private swimming pool and a garden. This lovely apartment has a private car parking and a stunning view over the hills. The village is only 25 min. from Pisa Airport and 35 min. from the coast.

Villa in Castiglion d'orcia

4.96 out of 5 average rating, 105 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Home in San Casciano in Val di pesa

4.83 out of 5 average rating, 88 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Villa in Petrignano

4.98 out of 5 average rating, 51 reviews

Restored Farmhouse & Cottage with AC, Pool & WIFI

Villa La Quercia is a private 2 acre property consisting of a beautifully restored farmhouse and cottage- both exclusively for you during your stay. The property is surrounded by farmland and forest providing complete privacy and tranquility, yet the nearest village is only 3kms away. The property comfortably sleeps up to 12 people and has a large salt water filtered swimming pool. Fabulous restaurants, wineries and stunning Tuscan & Umbrian villages are but a short drive. Welcome.

Home in Cerbaia

4.9 out of 5 average rating, 21 reviews

Podere Villanuova 2

Cute apartment in the tuscan countryside with a beautiful pool, set in Cerbaia, 20 km away from Florence. It is in a great position to visit many of the highlights of Tuscany and the wine region of Chianti. We rent a small apartment that has a living room with kitchen, a main bedroom, one bathroom. The house has a beautiful and spacious garden with a big pool overlooking the tuscan hills. In the property there is the villa of the owners and another apartment that we rent here on airbnb.

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Villa in Siena

4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

Truthful Tuscan paradise just 12mins from Siena. Boasting two doubles and two twins, 3 bathrooms, a very large leaving room, a beautiful dining room with fire place, park, parking and pool are all private. It is the ideal old and authentic family retreat, nestled on top of the Montechiaro hill with 360 degrees views over Chianti. The host leaves in the adjacent house. In winter and early spring there is an extra charge of 50€ a day for heating.

Rental unit in Morrona

4.85 out of 5 average rating, 13 reviews

Charming apartment with pool

Imagine your nest in the heart of the main square of an ancient village - a cozy and familiar refuge, also for bike lovers, strategically located in the center of the Pisa-Florence-Siena triangle. From here, you can quickly reach the iconic destinations and cultural wonders of Tuscany. This apartment, with its private garden, pool, barbecue area, bike storage, and panoramic view of the hills, ensures you a vacation like no other.

Rental unit in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

Unique experience in a real, old Tuscan farmhouse. Podere Casa Muricce is the place for people who love nature, animals, woods, but also close to the main places of interest in Tuscany. Situated on the top of a hill high 400mt, carefully restructured according to the tradition, Casa Muricce is the typical ancient Tuscany house in stone: all the furnishings, even doors, are original from Tuscany houses of `700/'800.

Farm stay in Sanfatucchio

4.88 out of 5 average rating, 181 reviews

2 room apartments in farmhouse whit pool

We have 4 apartments of this type on first floor and on two levels with two bedrooms (one double and a single bedroom), living room with kitchenette, bathroom with shower. The farmhouse enjoys a 360° view of the Umbrian and Tuscan hills and has a garden and shared swimming pool in summer, lounge and playground. This typology can NOT be booked with CHILDREN UNDER 12 or babies and is for max 3 people.

Vacation rentals for every style

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Popular amenities for Siena rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Civitella in Val di Chiana

4.93 out of 5 average rating, 45 reviews

Casa Fattore - Tuscan countryside house

Home in Montopoli in Val D'arno

4.93 out of 5 average rating, 42 reviews

Villa Due Pini Marti with private pool

Home in Firenze

5 out of 5 average rating, 8 reviews

La Torretta Luxury Private Pool

Home in Gambassi Terme

4.85 out of 5 average rating, 27 reviews

Finest country house. 3 bed rooms and shared pool

Home in San Lorenzo

5 out of 5 average rating, 12 reviews

Country Home w/outdoor organic Hot Tub

Home in Montagnano

4.99 out of 5 average rating, 69 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Home in Casanova

4.89 out of 5 average rating, 36 reviews

Casa Liliana

Home in Lucignano

4.91 out of 5 average rating, 22 reviews

Farmhouse with private pool

Condo rentals with a pool

Condo in Loro Ciuffenna

5 out of 5 average rating, 9 reviews

""Beautiful Villa with PRIVATE pool in Tuscany""

Condo in Ortignano

4.75 out of 5 average rating, 4 reviews

Castle with private pool

Condo in Bibbiena

5 out of 5 average rating, 16 reviews

ideal for two + loggia, pool on the farm

Condo in Volterra

4.95 out of 5 average rating, 21 reviews

Three-room apartment with 2 bedrooms and private garden, pool

Condo in Gavinana

5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

Condo in San Casciano in Val di Pesa

4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

Condo in Gambassi Terme

4.89 out of 5 average rating, 45 reviews

Panoramic apartment with BBQ primevideo pool

Condo in Montieri

5 out of 5 average rating, 25 reviews

PodereCupiano "Le Fornaci"

Home rentals with a private pool

Villa in Impruneta

4.99 out of 5 average rating, 93 reviews

Welcome Home - 8 miles to Florence & heated pool

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 186 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Home in Pergaccio

5 out of 5 average rating, 46 reviews

Villa Pergo is an ancient charming country villa

Farm stay in arezzo

4.98 out of 5 average rating, 221 reviews

Explore nature in the center of Vigneti Chianti

Villa in San Miniato

4.88 out of 5 average rating, 40 reviews

Villa with exclusive pool

Home in San Casciano in Val di pesa

5 out of 5 average rating, 41 reviews

Charming villa with pool in the Chianti hills

Villa in Cortona

4.93 out of 5 average rating, 46 reviews

Agriturismo Henni panoramic pool sauna and jacuzzi

Home in Tavarnelle Val di Pesa

4.93 out of 5 average rating, 92 reviews

Casa Luigi Suite with Exclusive Pool

Quick stats about vacation rentals with a pool in Siena

Total rentals
110 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

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