
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 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.

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.

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

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.

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

Poggio dell'orso.Traditional Casale. Amazing views
Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

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.

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 .

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

Infinity pool in Chianti area

Cottage surrounded by nature

StageROOM03 - Idyllic Chianti cottage near Siena

Cercis - La Palmierina

Vineyards Paradise

Country House in the Crete Senesi

Nada Home

Luxury Villa with a fantastic view
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

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

Guidoccio-Cosona Agritourism

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - ''Trebbiano'' villa

House between Firenze, Arezzo, chianti e Siena

Manuela apartment with pool in farmhouse

La Casetta
Home rentals with a private pool

Il Cipresso by Interhome

Sole 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

Historic home with exclusive pool

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 | G$40,948Â GYD | G$45,545Â GYD | G$42,411Â GYD | G$44,500Â GYD | G$47,007Â GYD | G$49,932Â GYD | G$53,901Â GYD | G$58,289Â GYD | G$51,185Â GYD | G$43,664Â GYD | G$40,739Â GYD | G$39,068Â GYD |
| 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 G$10,446Â GYD 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 270 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
420 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
- Feniglia
- Cala Violina
- Gulf of Baratti
- Kite Beach Fiumara
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Cala Di Forno
- Castiglion del Bosco Winery
- Riva del Marchese
- Marina di Grosseto beach
- Golf Club Toscana
- Santa Maria della Scala
- Pubblico Palace
- Cavallino Matto
- 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
- Things to do Siena
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- Things to do Tuscany
- Wellness Tuscany
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- Tours Tuscany
- Things to do Italy
- Food and drink Italy
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- Wellness Italy
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