
Vacation rentals with a pool in Montalcino
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Top-rated rentals with a pool in Montalcino
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

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.

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

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.

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

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

Typical Tuscan country house
Agriturismo Il Colle is located on one of the Chianti hills. The property 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 This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Villa in Montepulciano with a Pool
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * Pool open from April to November. Circular warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *

Cappella - farmhouse surrounded by vineyards
The Cappella apartment is part of the Le Chiuse agritourism, a property dating back to 1840, surrounded by vineyards. It is housed in 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 loft with a double bed. Equipped with air conditioning. The window of the master bedroom is equipped with a mosquito net. Pool open June-October
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Italian Internal

Cottage surrounded by nature

Infinity pool in Chianti area

Private Chianti Cottage, Garden & Vineyard Views

Cercis - La Palmierina

Vineyards Paradise

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Nada Home
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Casa Biancospino Crete Senesi | Podere Fossaccio

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Orgiale Charme Residenz Castle
Home rentals with a private pool

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa

Explore nature in the center of Vigneti Chianti
Historic villa x8 with exclusive pool

Magnificent Tuscan Villa, amazing interiors & view
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ977 | ﺩ.ﺇ870 | ﺩ.ﺇ889 | ﺩ.ﺇ782 | ﺩ.ﺇ826 | ﺩ.ﺇ878 | ﺩ.ﺇ948 | ﺩ.ﺇ1,025 | ﺩ.ﺇ900 | ﺩ.ﺇ859 | ﺩ.ﺇ955 | ﺩ.ﺇ973 |
| 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 400 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 8,470 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
390 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
- Cala Violina
- Feniglia
- Del Chianti
- Centro Storico Orvieto
- Gulf of Baratti
- Cascate del Mulino
- Siena Cathedral
- Palazzo Pubblico
- La Scarzuola
- Parco Regionale Della Maremma
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- CavallinoMatto
- Santa Maria della Scala
- Saturnia Thermal Park
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Basilica Di San Miniato A Monte
- Mount Amiata
- Casa Barthel
- Things to do Montalcino
- Food and drink Montalcino
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- Art and culture Siena
- Things to do Tuscany
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