
Vacation 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.

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.

Pieve di Caminino Historic Farm
Only for nature lovers. The ancient organic Pieve di Caminino farm is an important historical site: a former medieval parish church built at the intersection of two Roman roads, it hosted two saints (the 12th-century church is now a private museum, which can be visited by guests by appointment). Today it covers 200 hectares of fenced private property, located on a panoramic hill. Seven accommodations share an estate with a swimming pool (seasonal), two ponds, a centenary olive grove, vineyard and a cork forest.

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.

Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

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

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

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.

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

Il Nido - a romantic fire pit
Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

Panoramic Country Suite Montalcino
Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Cottage surrounded by nature

StageROOM03 - Idyllic Chianti cottage near Siena

Vineyards Paradise

Charming estate with views

Antico Borgo Ripostena – n. 8 Old House

Country House in the Crete Senesi

Gaiole in Chianti Poggio Casabianca

House Rigomagno Siena
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

La Loggia, farmhouse apartment

48 sqm cottage, swimming pool, relaxation, surrounded by greenery

La Foresteria | Granary House

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

Manuela apartment with pool in farmhouse

Poggio ai Gelsi, Melograno Lodge
Home rentals with a private pool

La Felcaia by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Podere Vignali by Interhome

Melograno by Interhome

Villa Pergo is an ancient charming country villa

Explore nature in the center of Vigneti Chianti

Podere San Lorenzo 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 | $274 CAD | $305 CAD | $284 CAD | $298 CAD | $315 CAD | $334 CAD | $304 CAD | $337 CAD | $353 CAD | $291 CAD | $273 CAD | $262 CAD |
| 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 430 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 8,250 verified reviews to help you choose

Family-friendly vacation rentals
290 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 270 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wifi availability
420 of Montalcino vacation 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
- Provence Vacation rentals
- Rome Vacation rentals
- Molfetta Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Cannes Vacation rentals
- Italian Riviera Vacation rentals
- Bologna Vacation rentals
- Bed and breakfasts Montalcino
- Rentals with outdoor seating Montalcino
- Rentals with an EV charger Montalcino
- Rentals with a firepit Montalcino
- Cottage rentals Montalcino
- Family-friendly rentals Montalcino
- Rentals with breakfast Montalcino
- Smoking-friendly rentals Montalcino
- Rentals with a sauna Montalcino
- Vacation home rentals Montalcino
- Fitness-friendly rentals Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with a fireplace Montalcino
- Farmstay rentals Montalcino
- Rentals with a hot tub Montalcino
- Luxury rentals Montalcino
- Rentals with a washer and dryer Montalcino
- Rentals with a patio Montalcino
- Condo rentals Montalcino
- Hotel rentals Montalcino
- House rentals Montalcino
- Apartment rentals Montalcino
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cala Di Forno
- Tenuta Le Velette
- Marina di Grosseto beach
- Castiglion del Bosco Winery
- Riva del Marchese
- Golf Club Toscana
- Santa Maria della Scala
- Cavallino Matto
- Pubblico Palace
- Cantina Stefanoni
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Casa Del Cioccolato Perugina
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Things to do Montalcino
- Food and drink Montalcino
- Nature and outdoors Montalcino
- Things to do Siena
- Sightseeing Siena
- Tours Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Things to do Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Things to do Italy
- Tours Italy
- Food and drink Italy
- Sports activities Italy
- Wellness Italy
- Nature and outdoors Italy
- Entertainment Italy
- Art and culture Italy
- Sightseeing Italy