
Vacation rentals with a pool in Montalcino
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Montalcino

Total vacation rentals
Explore 400 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 8,470 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
390 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!
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.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

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.

Infinity view
Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

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.

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Private Chianti Cottage, Garden & Vineyard Views
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.

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

EcoLodge – modern design in a peaceful panoramic location
The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

Appaloosa - Apartment for couples and families
Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.

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

Cottage surrounded by nature

Infinity pool in Chianti area

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Nada Home

Country House in the Crete Senesi

Borgo Ripostena – No. 8 Casa Vecchia
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Scenic Stilish Country

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Tuscany accommodation with panoramic view terrace

Manuela apartment with pool in farmhouse

Orgiale Charme Residenz Castle
Home rentals with a private pool

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Casa Luigi Suite with exclusive pool

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa

Explore nature in the center of Vigneti Chianti

Magnificent Tuscan Villa, amazing interiors & view
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ977 | ﺩ.ﺇ870 | ﺩ.ﺇ889 | ﺩ.ﺇ782 | ﺩ.ﺇ826 | ﺩ.ﺇ878 | ﺩ.ﺇ948 | ﺩ.ﺇ1,025 | ﺩ.ﺇ900 | ﺩ.ﺇ859 | ﺩ.ﺇ955 | ﺩ.ﺇ973 |
| 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 |
Destinations to explore
- Provence Vacation rentals
- Rome Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Venice Vacation rentals
- Florence Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Italian Riviera Vacation rentals
- Cannes Vacation rentals
- Bologna Vacation rentals
- Bonifacio Vacation rentals
- Rentals with breakfast Montalcino
- Apartment rentals Montalcino
- Luxury rentals Montalcino
- Rentals with outdoor seating Montalcino
- Rentals with a fireplace Montalcino
- Rentals with a hot tub Montalcino
- Rentals with a fire pit Montalcino
- Vacation home rentals Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with a sauna Montalcino
- Rentals with an EV charger Montalcino
- Smoking-friendly rentals Montalcino
- Condo rentals Montalcino
- Hotel rooms Montalcino
- Fitness-friendly rentals Montalcino
- Cottage rentals Montalcino
- Bed and breakfasts Montalcino
- Farmstay rentals Montalcino
- House rentals Montalcino
- Family-friendly rentals Montalcino
- Rentals with a washer and dryer Montalcino
- Rentals with a patio Montalcino
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Feniglia
- Centro Storico Orvieto
- Del Chianti
- Gulf of Baratti
- Palazzo Pubblico
- Siena Cathedral
- Cascate del Mulino
- La Scarzuola
- Santa Maria della Scala
- Parco Regionale Della Maremma
- Antinori nel Chianti Classico
- CavallinoMatto
- Ugolino Golf Club
- Basilica Di San Miniato A Monte
- Saturnia Thermal Park
- Terme San Filippo
- Mount Amiata
- Vulci
- Casa Barthel
- Abbey of Sant'Antimo
- The Riserva Naturale Della Laguna Di Orbetello
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Tours Siena
- Sports activities Siena
- Food and drink Siena
- Art and culture Siena
- Things to do Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Things to do Italy
- Food and drink Italy
- Tours Italy
- Sports activities Italy
- Wellness Italy
- Entertainment Italy
- Sightseeing Italy
- Nature and outdoors Italy
- Art and culture Italy







