
Holiday rentals with a pool in Montepulciano
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Montepulciano

Total holiday rentals
Explore 20 holiday rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at £74 per night before taxes and fees

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Over 620 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
20 of Montepulciano holiday rentals include wifi 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
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.

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.

House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.

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.

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. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

2 room apartments in farmhouse whit pool
We have 4 apartments of this type on first floor and on two levels with two bedrooms (one double and a single bedroom. The single bedroom is in the attic and has no door it overlooks the living room), living room with kitchenette, bathroom with shower. The farmhouse enjoys a 360° view of the Umbrian and Tuscan hills and has a garden and shared swimming pool in summer, lounge and playground. This typology can NOT be booked with CHILDREN UNDER 12 or babies and is for max 3 people.

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 warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *

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.

Conca d'Oro villa with private pool, sleeps 4
Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi
Popular amenities for Montepulciano rentals with a pool
House rentals with a pool

Casa Lucy

Cottage surrounded by nature

Private Chianti Cottage, Garden & Vineyard Views

Il nido del Rondone

Traditional stone house in Tuscany

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Luxury Villa with a fantastic view

Nada Home
Apartment rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Casa Granaio | Ground floor 1-bedroom apartment (2

Girasole Apartment

House between Firenze, Arezzo, chianti e Siena

Ancient 17th-century farm in Chianti, Tuscany

Poggio ai Gelsi, Melograno Lodge

Charming Residence Castello di Orgiale near Siena

La Casetta
Home rentals with a private pool

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool

Wp Relais Borgo Vignalunga

Stone House with Exclusive Pool Codilungo in Chianti

Explore nature in the center of Vigneti Chianti

Agriturismo Henni panoramic pool sauna and jacuzzi
Destinations to explore
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- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Mount Amiata
- Eremo Di Camaldoli
- Palazzo Pubblico
- Siena Cathedral
- Mount Subasio
- Vulci
- Antinori nel Chianti Classico
- Ugolino Golf Club
- Val di Chiana
- Terme San Filippo
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Saturnia Thermal Park
- Things to do Montepulciano
- Food and drink Montepulciano
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Sports activities Siena
- Entertainment Siena
- Food and drink Siena
- Nature and outdoors Siena
- Tours Siena
- Things to do Tuscany
- Art and culture Tuscany
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- Entertainment Tuscany
- Sightseeing Tuscany
- Wellness Tuscany
- Food and drink Tuscany
- Tours Tuscany
- Nature and outdoors Tuscany
- Things to do Italy
- Wellness Italy
- Sports activities Italy
- Sightseeing Italy
- Entertainment Italy
- Food and drink Italy
- Art and culture Italy
- Nature and outdoors Italy
- Tours Italy







