
Vacation rentals with a pool in Montalcino
Find and book unique homes with a pool on Airbnb
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

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

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.

Case nell'aia Arco, apartment in Chianti and pool
L'appartamento Arco si trova in un tipico borgo toscano tra vigneti e oliveti. Appartamento arredato in stile rustico toscano, accogliente per farvi rilassare e visitare la zona. L'appartamento si affaccia sulla grande terrazza dove potete fare pranzi e cene all'aperto o aperitivi. Cucina, divano e punto TV, wifi, due camere matrimoniali, bagno, terrazza, piscina. Parcheggio auto nella proprietà . Ideale come punto di partenza per visitare Siena, Firenze, San Gimignano, sia in auto che in bici.

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.

Vineyards Paradise
Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).

Private Chianti Cottage, Garden & Vineyard Views
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.

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.

EcoLodge – modern design in a peaceful panoramic location
The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

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

Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Agriturismo Palazzi del Papa Val d'Orcia Pienza
Farmhouse Palazzo del Papa, with an apartment with 3 double bedrooms, 2 bathrooms, 1 fully equipped kitchen, a large living room, equipped with air conditioning, to spend time with friends or family. On request breakfast and dinner with the products of our farm. Pool and garden wi-fi for our guests.
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Cottage surrounded by nature

Cercis - La Palmierina

Il nido del Rondone

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Luxury Villa with a fantastic view

Country House in the Crete Senesi

Antico Borgo Ripostena – n. 8 Old House
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti

Orgiale Charme Residenz Castle
Home rentals with a private pool

Wp Relais Borgo Vignalunga

Stone House with Exclusive Pool Codilungo in Chianti

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

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ720 | ﺩ.ﺇ801 | ﺩ.ﺇ746 | 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 |
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- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Feniglia
- Cascate del Mulino
- Basilica Di San Miniato A Monte
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Pubblico
- CavallinoMatto
- Santa Maria della Scala
- Ugolino Golf Club
- Antinori nel Chianti Classico
- Parco Regionale Della Maremma
- Siena Cathedral
- Abbey of Monte Oliveto Maggiore
- Casa Barthel
- La Scarzuola
- Val di Chiana
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Cathedral of San Lorenzo
- Terme San Filippo
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
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- Art and culture Siena
- Tours Siena
- Things to do Tuscany
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