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Holiday rentals with a pool in Montalcino

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Montalcino

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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

Appartamento Spinosa a Podere Capraia

App.to di due locali su due piani, recentemente ristrutturato con arredamento di buon gusto: soggiorno con divano letto (1 piazza e mezza), tavolo da pranzo, TV, WiFi. Angolo cottura con forno , frigo e lavastoviglie. Bagno con doccia, Wc, bidet. Piano superiore camera matrimoniale mansardata, aperta. Uscita su patio antistante attrezzata. Riscaldamento (dal 15/10 al 15/04) , zanzariere. Ammessi animali piccola media taglia. Piscina ( aperta dal 01/06 al 30/09) condivisa con appartamento Solengo

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.

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 - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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

Casa indipendente, due camere da letto matrimoniali, due bagni con doccia, living con cucina completa di tutto (lavastoviglie, lavatrice, forno, microonde), divano letto matrimoniale, giardino privato con pergola attrezzato. Tv Sat e Free wifi. Servizi aggiuntivi in struttura, su prenotazione, biciclette a pedalata assistita marca Focus modello Jarifa2 6.7 e un'area wellness con sauna finlandese da esterni Forest e una minipiscina idromassaggio riscaldata con cromoterapia con vista panoramica.

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.

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 293 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

Guest favourite
A spacious living area is highlighted by rustic wooden beams and a cozy fireplace. A light-colored sofa is positioned near large windows, allowing natural light to fill the space. A dining table is set with fresh produce and a decorative vase, enhancing the inviting atmosphere.
Home in Anghiari
4.89 out of 5 average rating, 147 reviews

Poggiodoro, your charming villa in Tuscany

Welcome to Poggiodoro, our 16th century stones' villa located in the countryside of Anghiari. The House offers stunning views, charming and furnished interiors providing all type of comforts: a beautiful fireplace that will keep the ambient warm even in winter, a big private garden where you can enjoy the open air and have lunch under the shade of pergola, with BBQ, fantastic in the warm seasons, a panoramic pool to spend great moments with friends, to be shared with the hamlet guests

Top Guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 140 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

Guest favourite
A welcoming kitchen area features wooden elements and vibrant yellow walls. A dining table with chairs is positioned beside a large glass door leading to the garden. Natural light filters through the curtains, enhancing the inviting atmosphere, while a red rug adds a pop of color to the floor.
Farm stay in Murlo
4.97 out of 5 average rating, 177 reviews

Country house near Siena

The apartment is on the ground floor of a farmhouse of 1600, it is very cozy, the floors are in wood and the walls are painted in bright colors. The house consists of a large kitchen, a bedroom where there is also a sitting area with a comfortable sofa that can accommodate two people and a fireplace near the sofa. The house is surrounded by beautiful hills and woods. In front of the house there is a terrace where to eat, and a garden with deckchairs.

Guest favourite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona
4.96 out of 5 average rating, 140 reviews

Poggio dell'orso.Traditional Casale. Amazing views

Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

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, 246 reviews

Il Nido - un romantico focolare

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.

Guest favourite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino
4.89 out of 5 average rating, 380 reviews

Panoramic Country Suite Montalcino

Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.

Popular amenities for Montalcino rentals with a pool

When is the best time to visit Montalcino?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$351 NZD$390 NZD$363 NZD$381 NZD$402 NZD$427 NZD$461 NZD$499 NZD$438 NZD$374 NZD$349 NZD$334 NZD
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Quick stats about holiday rentals with a pool in Montalcino

  • Total holiday rentals

    Explore 430 holiday rentals in Montalcino

  • Nightly prices starting at

    Montalcino holiday rentals start at $89 NZD per night before taxes and fees

  • Verified guest reviews

    Over 8,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    290 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 270 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    420 of Montalcino holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Montalcino rentals

  • 4.8 Average rating

    Montalcino stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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