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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.

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Top Guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5 out of 5 average rating, 184 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 117 reviews

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.

Top Guest favourite
A stone wall is adorned with vibrant red climbing roses, creating a striking contrast against the rustic texture. A window with a black grid pattern is visible, framed by the lush greenery of surrounding plants, enhancing the inviting character of the setting.
Home in Castellina in Chianti
4.96 out of 5 average rating, 108 reviews

Leonardo - Chianti/Siena, Florence, San Gimignano.

Ancient stone house from the 15th century in a small renovated medieval hamlet in the heart of the Chianti Classico. Located on top of a hill between Florence, Siena and San Gimignano. TENNIS COURT+ SWIMMING POOL Splendid view over the valley. Independent entrance; On the ground floor: large living room with two sofas, dining area and open kitchen. On the 1st floor: 2 bedrooms and 1 bathroom with shower; Private garden with terrace - table and chairs for eating under the gazebo and sun loungers

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 207 reviews

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.

Top Guest favourite
Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.
Apartment in Asciano
4.94 out of 5 average rating, 141 reviews

Loggiato 2 Apartment in Tuscany with pool

The Loggiato 2 apartment for 2 people is located in the Santa Lucia farmhouse (THE FARMHOUSE IS DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is a two-room apartment located on the first floor with a private table in front of the windows of the entrance loggia. There is a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen and television. The apartment has air conditioning in the room (for a fee).

Guest favourite
Cottage in Castellina in Chianti
4.96 out of 5 average rating, 104 reviews

Cottage Vittoria - Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Cappero (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Top Guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 127 reviews

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.

Guest favourite
A sunlit sunroom features large windows adorned with sheer curtains, allowing natural light to fill the space. A cozy white sofa is positioned next to a small wooden table with chairs, while indoor plants add a touch of greenery to the inviting atmosphere.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 280 reviews

Charming estate with views. A/C in the bedrooms

The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.

Top Guest favourite
A serene landscape showcases a rustic stone building surrounded by tall cypress trees, offering a touch of greenery to the well-maintained lawn. The backdrop reveals gentle hills under a clear blue sky, creating a peaceful countryside atmosphere.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 474 reviews

Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

Guest favourite
A private terrace is seen with a metal table and two chairs, framed by colorful wildflowers. In the background, rolling hills stretch towards the horizon, while lush greenery fills the landscape. A gentle breeze moves through, creating a serene setting.
Holiday home in Casole d'Elsa (SI)
4.89 out of 5 average rating, 239 reviews

Studio in Tuscan farmhouse with pool & views

The studio is nestled in a beautiful Tuscan farmhouse on an olive farm near Casole d'Elsa, an unspoilt hilltop town in central Tuscany. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds.

Top Guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano
4.96 out of 5 average rating, 190 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Top Guest favourite
A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.
Loft in Siena
4.95 out of 5 average rating, 245 reviews

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

Popular amenities for Siena rentals with a pool

When is the best time to visit Siena?

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Avg. price$217 AUD$196 AUD$306 AUD$348 AUD$397 AUD$471 AUD$414 AUD$365 AUD$387 AUD$362 AUD$324 AUD$328 AUD
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Quick stats about holiday rentals with a pool in Siena

  • Total holiday rentals

    Explore 80 holiday rentals in Siena

  • Nightly prices starting at

    Siena holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,020 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

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 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

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