
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.

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.

Loggiato 2 Apartment in Tuscany with pool
The Loggiato 2 apartment for 2 people is located in the Santa Lucia farmhouse (THE FARMHOUSE IS DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is a two-room apartment located on the first floor with a private table in front of the windows of the entrance loggia. There is a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen and television. The apartment has air conditioning in the room (for a fee).

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.

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

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

Farmhouse surrounded by vineyards - Rosmarino
The Rosmarino apartment is part of the Le Chiuse farm, an 1840s property immersed in the vineyards. It consists of a living room with kitchenette, sofa and fireplace with ceiling fan, a double bedroom with air conditioning, a second bedroom with two single beds that can be converted into a double bed if necessary, also with air conditioning, a bathroom with shower. All windows are equipped with shutters and mosquito nets. The opening of the pool is seasonal

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.

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

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.

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

Cozy country house Podere Scorno with pool

Italian Interior

StageROOM03 - Idyllic Chianti cottage near Siena

Villa Casabella near Siena

Vineyards Paradise

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Nada Home
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Studio apartment

Casa Biancospino Crete Senesi | Fossaccio Farm

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

Manuela apartment with pool in farmhouse

Poggio ai Gelsi, Melograno Lodge

La Casetta
Home rentals with a private pool

Il Cipresso by Interhome

La Felcaia by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Podere Vignali by Interhome

Villa Pergo is an ancient charming country villa

Explore nature in the center of Vigneti Chianti

Organic Wellness Oasis by Interhome

Podere Molinaccio - Luxury Tuscan-style Eco Villa
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $252 SGD | $280 SGD | $261 SGD | $274 SGD | $289 SGD | $307 SGD | $332 SGD | $359 SGD | $315 SGD | $269 SGD | $251 SGD | $240 SGD |
| 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 $64 SGD 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!
Destinations to explore
- House rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with a patio Montalcino
- Holiday home rentals Montalcino
- Hotel rooms Montalcino
- Bed and breakfasts Montalcino
- Rentals with a fireplace Montalcino
- Rentals with a firepit Montalcino
- Cottage rentals Montalcino
- Rentals with an EV charger Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Flat rentals Montalcino
- Fitness-friendly rentals Montalcino
- Rentals with a sauna Montalcino
- Rentals with a hot tub Montalcino
- Farm stay rentals Montalcino
- Rentals with outdoor seating Montalcino
- Luxury rentals Montalcino
- Family-friendly rentals Montalcino
- Apartment rentals Montalcino
- Smoking-friendly rentals Montalcino
- Rentals with a washing machine and dryer Montalcino
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Siena Cathedral
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Pubblico
- Santa Maria della Scala
- CavallinoMatto
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Casa Barthel
- Cascate del Mulino
- Antinori nel Chianti Classico
- Argentario Golf Resort & Spa
- Mount Amiata
- Castello di Volpaia
- Val di Chiana
- Castello di Verrazzano
- Riserva Naturale Diaccia Botrona
- San Gimignano 1300
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Tours Siena
- Sightseeing Siena
- Sports activities Siena
- Food and drink Siena
- Art and culture Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Nature and outdoors Italy
- Wellness Italy
- Tours Italy
- Entertainment Italy
- Art and culture Italy
- Sports activities Italy
- Sightseeing Italy
- Food and drink Italy




