
Vacation 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.

Loggiato 3 apartment in Tuscany near Siena
The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

Ancient 17th-century farmhouse in Chianti, Tuscany
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. The apartment is furnished in the perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and thoughtful furnishings and products from local artisans that will help you enjoy a pleasant stay . In the large outdoor courtyard you'll find a salt pool on a panoramic terrace with wonderful views of castle hills and vineyards with breathtaking 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.

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.

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.

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.

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

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.

Explore nature in the center of Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Podere Guidi
Apartment in a panoramic villa between Florence and Siena in the heart of Chianti in a charming village. The swimming pool is open from May 1st to September 30th, from 9 a.m. to 1 p.m. with exclusive use for guests during this time. For different needs, ask the host.

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
House rentals with a pool

Italian Interior

StageROOM03 - Idyllic Chianti cottage near Siena

Ancient Barn in Chianti with Pool

Vineyards Paradise

Explore Chianti from a Charming Stone House

Antico Borgo Ripostena – n. 8 Old House

Casa di Lyndall - Entire house with exclusive pool

Nada Home
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

48 sqm cottage, swimming pool, relaxation, surrounded by greenery

La Foresteria | Granary House

Guidoccio-Cosona Agritourism

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

Manuela apartment with pool in farmhouse

Tenuta di Pomine Certaldo (Fi) Edera Apartment
Home rentals with a private pool

La Felcaia by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Podere Vignali by Interhome

Melograno by Interhome

Villa Pergo is an ancient charming country villa

Podere San Lorenzo by Interhome

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Casa Frati by Interhome
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,030 GYD | G$45,635 GYD | G$42,495 GYD | G$44,589 GYD | G$47,101 GYD | G$50,032 GYD | G$54,009 GYD | G$58,405 GYD | G$51,288 GYD | G$43,751 GYD | G$40,821 GYD | G$39,146 GYD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about vacation rentals with a pool in Montalcino

Total vacation rentals
Explore 430 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at G$10,467 GYD per night before taxes and fees

Verified guest reviews
Over 8,250 verified reviews to help you choose

Family-friendly vacation rentals
290 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 270 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
420 of Montalcino vacation rentals include wi-fi access

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

4.8 Average rating
Montalcino stays are highly rated by guests—averaging 4.8 out of 5!
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- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Cala di Forno
- Castiglion del Bosco Winery
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Marina di Grosseto
- Santa Maria della Scala
- Cavallino Matto
- Palazzo Pubblico
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
- Things to do Montalcino
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- Art and culture Siena
- Things to do Tuscany
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