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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Antria

4.92 out of 5 average rating, 126 reviews

A charming Tuscan retreat

Villa Pianelli is a traditional farmhouse dating from the 1500's and consists of 2 structures. The main house where I live, always available to ensure your stay runs smoothly and the Garden apartment. Both are completely independant with separate entrances. The Garden apartment is composed of 5 rooms on ground level, the interiors have retained the Tuscan characteristics with brick ceilings and chestnut beams and terracotta floors. There are 2 double bedrooms, 1 bathroom with shower, 1 lounge with a wood burning stove and open plan kitchen - dining area. The kitchen is equipped with fridge,oven and ceramic hob. From the lounge you access the spa room with sauna and jacuzzi and from there onto a terraced garden complete with b.b.q. The swimming pool is 8mx16m and is open May through September, furnished with sun loungers,a b.b.q area and a large covered pergola with dining tables and chairs. Villa Pianelli is secluded in a quiet corner of the Tuscan countryside, nestled in the hills of Arezzo, surrounded by vineyards, olive groves and oak forests.We can offer our guests a dimension of peace and quiet whilst ensuring various possibilities of entertainment in wineries, restaurants,shopping etc just a few kilometres away in Arezzo.

Superhost

Home in Montespertoli

4.84 out of 5 average rating, 69 reviews

Holiday immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a vacation immersed in the Tuscan countryside, with a large equipped pool 🌞💐The scents of nature, the breathtaking landscapes and the swimming pool will be the setting for the relaxation you are looking for. 🚴🏻‍♂️🏃‍♀️Then if you feel the need to move around you can swim, walk, or run through the trails around your country home. 🏛The strategic location of the apartment allows you to hike in Florence, Siena and Pisa. ✨The apartments are recently renovated in Tuscan style.”

Guest favorite

Cottage in Castiglion Fibocchi

5 out of 5 average rating, 38 reviews

Castellin di Bocco Tuscan countryhouse with pool

A pochi chilometri da Arezzo la casa è parte di un edificio che risale al 1623. Completamente isolata ma a pochi km da Arezzo Una splendida e ampia piscina è a disposizione e allieterà le calde giornate. Sviluppata su due livelli ha tre camere da letto e due bagni, una cucina attrezzata che affaccia su una terrazza-giardino, due ampi salotti dotati di smart tv, wifi Per gli amanti dell'avventura e dello sport, è possibile noleggiare e-bike e percorrere i sentieri che si snodano tra le colline.

Guest favorite

Villa in Castiglion d'orcia

4.96 out of 5 average rating, 102 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Guest favorite

Home in San Casciano in Val di pesa

4.83 out of 5 average rating, 86 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Superhost

Villa in Petrignano

4.98 out of 5 average rating, 51 reviews

Restored Farmhouse & Cottage with AC, Pool & WIFI

Villa La Quercia is a private 2 acre property consisting of a beautifully restored farmhouse and cottage- both exclusively for you during your stay. The property is surrounded by farmland and forest providing complete privacy and tranquility, yet the nearest village is only 3kms away. The property comfortably sleeps up to 12 people and has a large salt water filtered swimming pool. Fabulous restaurants, wineries and stunning Tuscan & Umbrian villages are but a short drive. Welcome.

Guest favorite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Guest favorite

Villa in Siena

4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

Truthful Tuscan paradise just 12mins from Siena. Boasting two doubles and two twins, 3 bathrooms, a very large leaving room, a beautiful dining room with fire place, park, parking and pool are all private. It is the ideal old and authentic family retreat, nestled on top of the Montechiaro hill with 360 degrees views over Chianti. The host leaves in the adjacent house. In winter and early spring there is an extra charge of 50€ a day for heating.

Superhost

Rental unit in Tavernelle, Panicale

4.81 out of 5 average rating, 73 reviews

"Il Leccino": Delightful 1-bdr apt. in farmhouse.

Very panoramic 1-bedroom apt. Wooden beams, original features, fully-furnished kitchen, a.c., wifi. Sofa bed in living room, can sleep up to 3 guests. Infinity pool, terraces, barbecue. Surrounded by nature, in an organic olive-oil producing estate. This Farmhouse, divided into 5 apartments, has a beautiful infinity pool overlooking the valley. The pool usually opens around the 1st of June (this year it will open on the 27th of May).

Guest favorite

Rental unit in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

Unique experience in a real, old Tuscan farmhouse. Podere Casa Muricce is the place for people who love nature, animals, woods, but also close to the main places of interest in Tuscany. Situated on the top of a hill high 400mt, carefully restructured according to the tradition, Casa Muricce is the typical ancient Tuscany house in stone: all the furnishings, even doors, are original from Tuscany houses of `700/'800.

Guest favorite

Farm stay in Sanfatucchio

4.88 out of 5 average rating, 181 reviews

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), 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.

Guest favorite

Townhouse in Barberino Tavarnelle

4.96 out of 5 average rating, 81 reviews

Tower dating back to 1212 in the heart of Tuscany

In the heart of Tuscany, newly renovated apartment in old farmhouse restored from the ground up. Only 30 minutes from Florence and 40 from Siena. A/C in every room and screens on door and windows Extremely quiet, with all comforts including a common infinity pool with large private umbrella for shade. Relax outside with a glass of wine or tour around chianti from this conveniently located home.