
Vacation rentals with a pool in Montepulciano
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Montepulciano
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Ulivo - Charming apartment in the countryside
The independent, bright and welcoming apartment located on the ground floor of a renovated farmhouse from 1856, surrounded by green hills, consists of a large eat-in kitchen, a double bedroom with comfortable futon chair, independent bathroom. Triple exposure The apartment is equipped with: - centralized warming - fitted kitchen - bathroom with bathtub and shower - guest sheets and towels - stylish furnishings - veranda exclusive use with dining table overlooking the surrounding countryside.

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.

Separate room, between Cortona and Montepulciano
We are a small farm with a family-run farm on the border between Tuscany and Umbria. The old farmhouse in which we live with our children are surrounded by vineyards and olive groves with a splendid view of Montepulciano. We can sleep in 2 apartments and / or 1 independent room furnished with poor art and originality. In the large garden, available to all, there are two pools (one for children), games, organic vegetable garden. We have a restaurant Pierpaolo cooking the typical Tuscan dishes.

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY.

Farmhouse with swimming pool with wonderful view
Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests eight vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

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.

Casa Crociani - Amazing Pool & Free Parking
Just 4.7 km from Montepulciano (7 minutes by car), this house is located in a quiet position surrounded by greenery, with a splendid view of the Tuscan hills. The property is equipped with all the necessary amenities to ensure a pleasant stay, perfect for relaxing weekends or vacations. You can relax on the private patio, in the outdoor gardens, or spend unforgettable moments by the pool, enjoying the peace and beauty of the surrounding landscape.

Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.

Villa in Montepulciano with a Pool
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * Pool open from April to November. Circular heated pool, up to 32°C (90F) from April 7 to October 30 *
Popular amenities for Montepulciano rentals with a pool
House rentals with a pool

Infinity pool in Chianti area

Italian Internal

Vineyards Paradise

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

The Owl: view, pool and garden

Country House in the Crete Senesi
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Casa Granaio | Ground floor 1-bedroom apartment (2

Adalberto Apartment inside the Manor of Fulignano

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Spinosa Apartment in Podere Capraia

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

Villa Pergo is an ancient charming country villa

Charming villa in the Chianti hills

Agriturismo Henni panoramic pool sauna and jacuzzi

Casa Frati by Interhome

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool
Quick stats about vacation rentals with a pool in Montepulciano

Total vacation rentals
Explore 20 vacation rentals in Montepulciano

Nightly prices starting at
Montepulciano vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 360 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
20 of Montepulciano vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Montepulciano rentals

4.7 Average rating
Montepulciano stays receive an average rating of 4.7 out of 5 from guests
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- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Eremo Di Camaldoli
- Cascate del Mulino
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Terme Dei Papi
- Basilica of St Francis
- Mount Subasio
- Palazzo Pubblico
- Santa Maria della Scala
- Antinori nel Chianti Classico
- Rocca Maggiore
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Saturnia Thermal Park
- Pozzo di San Patrizio
- Castello di Verrazzano
- Vulci
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