Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
Top Guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.94 out of 5 average rating, 236 reviews

The Farmhouse Cottage

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 104 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
Apartment in Caminino
4.91 out of 5 average rating, 183 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

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, 202 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.

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 150 reviews

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.

Guest favourite
A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia
4.98 out of 5 average rating, 109 reviews

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.

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.

Top Guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in Barberino Tavarnelle
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Top Guest favourite
The exterior of a renovated stone house is framed by greenery, featuring large wooden doors that provide a welcoming entrance. An outdoor dining set is visible on the patio, surrounded by carefully maintained gardens and trees, evoking a serene countryside atmosphere.
Condo in Cinigiano
5 out of 5 average rating, 105 reviews

Spinosa Apartment in Podere Capraia

Two-room apartment on two floors, recently renovated with good taste furnishings: living room with sofa bed (1 and a half places), dining table, TV, WiFi. Kitchenette with oven, fridge and dishwasher. Bathroom with shower, toilet, and bidet. Upper floor, open attic double bedroom. Exit to equipped front patio. Heating (from 10/15 to 04/15), mosquito nets. Small and medium-sized pets allowed. Swimming pool (open from Jun. 1 to Sept. 30) shared with Solengo apartment

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

Guest favourite
A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.
Farm stay in Gaiole in Chianti
4.93 out of 5 average rating, 247 reviews

Il Nido - a romantic fire pit

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

Popular amenities for Siena rentals with a pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Rentals with pools