
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.

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.

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.

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.

"Lunetta" Private Apartment on Larger Property
Le Coppiole is an exciting new addition to our properties at the Ville Ferrano. This "agriturismo" is associated with our olive oil and wine activities. The property is situated in the midst of the most tranquil and breathtaking Tuscan countryside. We offer three homes for rent, either individually or together for a large group. The infinite edge pool is located to take advantage of the stunning views and sunsets. The Lunetta apartment is located on the second floor of the Lunette building.

Podere Ampella House with a Beautiful View
Newly restored peaceful charming townhouse in the the famous Val d'Orcia in the heart of Tuscany , The property sits on a gentle hill in a small hamlet offering stunning panoramic views and sunsets. Whether you visit with family, or friends, this house is perfect for offering ample private garden and a common pool, never crowed. The hamlet is just a short drive from the nearby beautiful towns and villages allowing easy access to explore the Tuscan sceneries, cultural and culinary delights.

Studio (2+1) in Val d'Orcia - Tuscany
A few steps from the historic center of medieval San Quirico d'Orcia and just 100 meters from the supermarket, a stay made of silence and the quiet passage of time, of days with a relaxing and regenerating atmosphere characteristic of the lifestyle in Val d'Orcia. The Taste of Tranquility is guaranteed by a 5000 sqm park that offers lawns and shady trees suitable for reading or simple relaxation. Ideal for a stay with an "antique" flavor", combined with all modern comforts.

Mimosa Apartment - Poggio al Vento
Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Cappella - farmhouse surrounded by vineyards
The Cappella apartment is part of the Le Chiuse agritourism, a 1840s structure surrounded by vineyards. It is obtained from a small deconsecrated church, consisting of a living room with a kitchenette, armchairs and a fireplace, a large double bedroom, a bathroom with a shower, a small room and a mezzanine with a double bed. Equipped with air conditioning. The window of the master bedroom is equipped with a mosquito net. The pool opening is SEASONAL.

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.

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.

Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Italian Internal

Infinity pool in Chianti area

StageROOM03 - Idyllic Chianti cottage near Siena

Mini country house Podere Scorno with pool

Vineyards Paradise

Antico Borgo Ripostena – n. 9 Oil Mill

Il nido del Rondone

Explore Chianti from a Charming Stone House
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Stone House in Chianti with pool and parking

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - Villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Manuela apartment with pool in farmhouse

La Casetta
Home rentals with a private pool

La Felcaia by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Podere Vignali by Interhome

Villa Pergo is an ancient charming country villa

Esplora la natura al centro di Vigneti Chianti

Historic home with exclusive pool

Charming villa in the Chianti hills

Agriturismo Henni panoramic pool sauna and jacuzzi
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $333 NZD | $370 NZD | $345 NZD | $362 NZD | $382 NZD | $406 NZD | $438 NZD | $474 NZD | $416 NZD | $397 NZD | $442 NZD | $450 NZD |
| 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 holiday rentals with a pool in Montalcino

Total holiday rentals
Explore 420 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at $85Â NZD per night before taxes and fees

Verified guest reviews
Over 8,340 verified reviews to help you choose

Family-friendly holiday rentals
280 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wifi availability
400 of Montalcino holiday rentals include wifi 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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- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Feniglia
- Cascate del Mulino
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- CavallinoMatto
- Santa Maria della Scala
- Palazzo Pubblico
- Siena Cathedral
- Riserva Naturale Diaccia Botrona
- Ugolino Golf Club
- Antinori nel Chianti Classico
- Casa Barthel
- Castello di Verrazzano
- Abbey of Monte Oliveto Maggiore
- Parco Regionale Della Maremma
- Pozzo di San Patrizio
- Val di Chiana
- Girifalco Fortress
- Vulci
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Sports activities Siena
- Sightseeing Siena
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- Food and drink Siena
- Art and culture Siena
- Nature and outdoors Siena
- Things to do Tuscany
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