
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.

Loggiato 3 apartment in Tuscany near Siena
The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

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 95 sqm
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.

StageROOM03 - Idyllic Chianti cottage near Siena
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.

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

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.

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.

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.
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Cozy country house Podere Scorno with pool

Italian Internal

Infinity pool in Chianti area

Cottage surrounded by nature

Villa Casabella near Siena

“il colle” nice house surrounded by vineyard

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House
Condo rentals with a pool

Farmhouse in Tuscany with pool and great views

Casa Biancospino Crete Senesi | Podere Fossaccio

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Manuela apartment with pool in farmhouse
Home rentals with a private pool

La Felcaia by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Podere Vignali by Interhome

Villa Pergo is an ancient charming country villa

Esplora la natura al centro di Vigneti Chianti

Organic Wellness Oasis by Interhome

Charming villa in the Chianti hills

Casa Frati by Interhome
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,015 GYD | G$45,619 GYD | G$42,480 GYD | G$44,573 GYD | G$47,084 GYD | G$50,014 GYD | G$53,990 GYD | G$58,384 GYD | G$51,269 GYD | G$48,967 GYD | G$54,408 GYD | G$55,455 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 420 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at G$10,463 GYD per night before taxes and fees

Verified guest reviews
Over 8,340 verified reviews to help you choose

Family-friendly vacation rentals
280 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
400 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!
Destinations to explore
- Provence Vacation rentals
- Rome Vacation rentals
- Molfetta Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Naples Vacation rentals
- Francavilla al Mare Vacation rentals
- Italian Riviera Vacation rentals
- Cannes Vacation rentals
- Bologna Vacation rentals
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with outdoor seating Montalcino
- Rentals with a patio Montalcino
- Smoking-friendly rentals Montalcino
- House rentals Montalcino
- Apartment rentals Montalcino
- Rentals with an EV charger Montalcino
- Rentals with a fireplace Montalcino
- Farmstay rentals Montalcino
- Rentals with a sauna Montalcino
- Condo rentals Montalcino
- Fitness-friendly rentals Montalcino
- Cottage rentals Montalcino
- Luxury rentals Montalcino
- Rentals with a hot tub Montalcino
- Hotel rooms Montalcino
- Bed and breakfasts Montalcino
- Rentals with a fire pit Montalcino
- Family-friendly rentals Montalcino
- Vacation home rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with a washer 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
- Lake Bolsena
- Cala Violina
- Feniglia
- Siena Cathedral
- Cascate del Mulino
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Pubblico
- Santa Maria della Scala
- CavallinoMatto
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Antinori nel Chianti Classico
- Casa Barthel
- Riserva Naturale Diaccia Botrona
- Saturnia Thermal Park
- Pozzo di San Patrizio
- Castello di Verrazzano
- Vulci
- Abbey of Sant'Antimo
- Val di Chiana
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Sightseeing Siena
- Food and drink Siena
- Tours Siena
- Sports activities Siena
- Art and culture Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Things to do Italy
- Sports activities Italy
- Tours Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Entertainment Italy
- Food and drink Italy
- Sightseeing Italy




