
Holiday 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.

Podere Vergianoni nestled in Chianti with a pool
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.

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.

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.

Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

S.Ilaria - Private pool Villa with 2 bedrooms
Sant'Ilaria it’s been lovingly renovated in 2016 into a luxury getaway in the countryside near Siena, with its 2 bedrooms it's the ideal escape. Watch the sun move across the landscape from a lounger by the pool and relax watching the amazing landscape in a total privacy. After sunset, heat up the barbecue for dinner at the al-fresco table or have a glass of local wine. This small and private villa has 2 bedrooms, all have private en-suite bathrooms.

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 - Italian Ground Coffee - 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.

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.

Charming cottage in Tuscany
Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available

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.

Beautiful medieval tower in Chianti
This is a lovely flat in an ancient farm, restored, in the heart of Chianti Classico , with an amazing panoramic view on the hills, surrounded by our vineyards as well as olive trees, where you will have an unforgettable holiday discovering Tuscany. CINIT048021B5LTBDVFE3

Elegant farmhouse Siena
The apartment of 200 square meters is part of a farmhouse of the 1600, it easily accommodates 6 people, it has 3 large bedrooms, a large living room, a kitchen with fireplace, two bathrooms and a breathtaking view, overlooking the Tuscan countryside up to Montalcino .
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Infinity pool in Chianti area

StageROOM03 - Idyllic Chianti cottage near Siena

Cottage surrounded by nature

Cercis - La Palmierina

Vineyards Paradise

Antico Borgo Ripostena – n. 9 Oil Mill

Leonardo - Chianti/Siena, Florence, San Gimignano.

House Rigomagno Siena
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

Casa Rebecca with a small private pool

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena
Home rentals with a private pool

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

Decameron house by Interhome

Agriturismo Henni panoramic pool sauna and jacuzzi

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 | $277 AUD | $308 AUD | $287 AUD | $301 AUD | $318 AUD | $338 AUD | $365 AUD | $395 AUD | $347 AUD | $331 AUD | $368 AUD | $375 AUD |
| 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 $71 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
400 of Montalcino holiday 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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- 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
- Sightseeing Siena
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- Nature and outdoors Siena
- Tours Siena
- Sports activities Siena
- Art and culture Siena
- Things to do Tuscany
- Food and drink Tuscany
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- Things to do Italy
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