
Holiday 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.

Casa Luigi Suite with exclusive pool
Come to this apartment: you will be welcomed by centuries of tranquility, and appreciate nature and relaxation. Carefully modernized (and with a swimming pool), this space embodies the roots of good Tuscan living – an equipped olive grove consisting of a pergola with a table and bathroom, a garden with a hammock and in the shade of pine and cypress trees, with chairs, deck chairs and a rocking chair, you can admire the rolling Chianti hills. Courtyard equipped with table and chairs. There is a beautiful elevated swimming pool with some games and a barbecue In addition to the farmhouse, the property includes an olive grove of about 1 hectare, in which equipped spaces have been created for complete relaxation. The Suite has a private entrance that leads directly to the upper floor of the farmhouse, allowing maximum privacy for guests. The farmhouse is part of a small old village inhabited by 4 very discreet and friendly family units. The suite's surface area is 90 square meters and consists of a dining room with kitchenette, large living room, double bedroom, bathroom with shower and a large attic (the door is 1.2 meters wide) with 3 single beds. A very bright environment and immersed in the complete tranquility of the countryside, it is equipped with air conditioning, satellite TV, and free 24-hour Wi-Fi. The owners provide the laundry area. Uncovered private parking. The owners are happy to welcome their guests and are available to resolve any issues. The small village is inhabited by three other very kind and discreet families, ready to help the guest. Tavarnelle is 25 km from Florence, 15 km from San Gimignano, 35 km from Siena. - Images of the exterior, swimming pool, garden and equipped olive grove will be visible soon. We kindly ask you to wait. The accommodation is about 5 km from the center of Tavarnelle. The historic center is equipped with all the services for the citizen and tourist: post office, police, municipality, emergency room, supermarket, trattorias, pizzerias, banks, etc. In addition, in the summer there are various musical events, small craft markets, and finally, every Thursday morning, the classic municipal market takes place. Places of interest (medieval villages) around Tavarnelle: San Donato in Poggio about 12 km. Barberino Val d'Elsa 6 km. Distances from art cities: Tavarnelle - Florence about 25 km Tavarnelle - San Gimignano/Monteriggioni about 20 km Tavarnelle - Siena about 35 km. In the organized outdoor spaces there is an ABOVE GROUND pool, the dimensions are: 10 meters X 5 meters, with a depth of 1.20 meters. A bathroom with shower completes the pool area. In the courtyard, guests have a nice table with barbecue. The entire olive grove area is at their disposal with maximum privacy. The owners, at the guest's request, can book hiking tours or wine-testing tours with the help of professionals. The price of any tour booking is not included in the price of the stay. The small village was once a military fortress, then a parish church or place of worship and from the beginning of the 20th century inhabited by farmers. Today it is inhabited by four very nice and discreet families ready to help the guest. Florence is 15.5 miles away and Siena is 21.7 miles away

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.

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.

Tuscan charm of villa - countryside - Villa Senaia
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

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.

Farmhouse close to Montepulciano
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 four 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.

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. *
Popular amenities for Montepulciano rentals with a pool
House rentals with a pool

Italian Internal

Infinity pool in Chianti area

Cottage surrounded by nature

Private Chianti Cottage, Garden & Vineyard Views

Vineyards Paradise

Borgo Ripostena – No. 5 Garage

Relaxation and charm in the Chianti hills

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Casa Biancospino Crete Senesi | Podere Fossaccio

Lornano Winery Farm - Villa ''Trebbiano''

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti

Castello di Orgiale Charme Residenz

La Casetta
Home rentals with a private pool

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa

TREEhouse / casaBARTHEL

Explore nature in the center of Vigneti Chianti
Quick stats about holiday rentals with a pool in Montepulciano

Total holiday rentals
Explore 30 holiday rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $170 NZD per night before taxes and fees

Verified guest reviews
Over 600 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
30 of Montepulciano holiday 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
Destinations to explore
- Pet-friendly rentals Montepulciano
- Rentals with breakfast Montepulciano
- Family-friendly rentals Montepulciano
- Rentals with a hot tub Montepulciano
- Apartment rentals Montepulciano
- Condo rentals Montepulciano
- House rentals Montepulciano
- Rentals with a fireplace Montepulciano
- Cottage rentals Montepulciano
- Villa rentals Montepulciano
- Rentals with outdoor seating Montepulciano
- Rentals with a patio Montepulciano
- Bed and breakfasts Montepulciano
- Smoking-friendly rentals Montepulciano
- Rentals with a washing machine and dryer Montepulciano
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Centro Storico Orvieto
- Basilica of St Francis
- Terme Dei Papi
- Cascate del Mulino
- Siena Cathedral
- Palazzo Pubblico
- Mount Subasio
- La Scarzuola
- Parco Regionale Della Maremma
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Eremo Di Camaldoli
- Santa Maria della Scala
- Saturnia Thermal Park
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Mount Amiata
- Vulci
- Val di Chiana
- Things to do Montepulciano
- Food and drink Montepulciano
- Things to do Siena
- Tours Siena
- Sports activities Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Food and drink Siena
- Art and culture Siena
- Things to do Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Nature and outdoors Italy
- Entertainment Italy
- Wellness Italy
- Tours Italy
- Sports activities Italy
- Art and culture Italy
- Sightseeing Italy







