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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.

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Rental unit in Castiglione del Lago

4.9 out of 5 average rating, 133 reviews

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.

Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 188 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Guest favourite

Condo in Noce

5 out of 5 average rating, 178 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to 1600 located in the beautiful hills of Chianti in Tuscany. The apartment is furnished in the perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and thoughtful and handcrafted furnishings that will make you enjoy a unique stay. In the large outdoor courtyard you will find at your disposal a large pool on a panoramic terrace with wonderful views of the hills and vineyards with unique sunsets.

Guest favourite

Farm stay in Montepulciano

4.95 out of 5 average rating, 154 reviews

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.

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 186 reviews

Tuscan charm of villa - countryside

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

Guest favourite

Home in Prato

4.98 out of 5 average rating, 124 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment, there might still be availability. Turquoise: https://www.airbnb.com/rooms/plus/9430389

Guest favourite

Villa in Montepulciano

4.95 out of 5 average rating, 132 reviews

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

Guest favourite

Rental unit in Castiglione del Lago

4.9 out of 5 average rating, 104 reviews

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.

Guest favourite

Villa in Montepulciano

4.9 out of 5 average rating, 111 reviews

Villa in Montepulciano with 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 March to November. Circular jacuzzi pool heated, up to 32°C from April to October *

Guest favourite

Home in Anghiari

4.99 out of 5 average rating, 211 reviews

Casa Rosmarino Eco-Wellness Country Home

Price Includes: - WELLNESS HOT TUB w/Jacuzzi Infrared SAUNA - FOOD & DRINKS 1 Welcome Aperitivo 1 Wine 1 Nespresso w/Capsules - COMFORT Heater 2 Night Included, Extra Night 25 Euro Shower Gel / Shampoo / Hair Dryers Bathrobes / Flips Flops Wood for the HotTub and Fireplace - EXTRA (not included) MASSAGES, COOKING CLASSES AND TASTING. Please INQUIRE for price & availability

Guest favourite

Farm stay in arezzo

4.98 out of 5 average rating, 214 reviews

Explore nature in the center of Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Guest favourite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 340 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

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Popular amenities for Montepulciano rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Orvieto

4.99 out of 5 average rating, 201 reviews

Vineyards Paradise

Guest favourite

Home in Foiano della Chiana

4.94 out of 5 average rating, 102 reviews

La Lisa: country house surrounded by fields

Home in Figline Valdarno

4.97 out of 5 average rating, 101 reviews

The Owl: view, pool and garden

Guest favourite

Home in Localita' Pievescola

4.94 out of 5 average rating, 162 reviews

Antico Borgo Ripostena – no. 8 Casa Vecchia

Guest favourite

Home in Asciano - Chiusure - Monte Oliveto Maggiore

4.96 out of 5 average rating, 174 reviews

Country House in the Crete Senesi

Home in Rietine

4.85 out of 5 average rating, 201 reviews

Gaiole in Chianti Poggio Casabianca

Guest favourite

Home in Subbiano

4.99 out of 5 average rating, 76 reviews

Romantic cosy flat - Toscana Italy

Guest favourite

Home in San Feliciano

4.9 out of 5 average rating, 138 reviews

Casa dei 5 Sensi - Trasimeno view

Condo rentals with a pool

Condo in Castelnuovo dei Sabbioni, caviglia

4.88 out of 5 average rating, 145 reviews

Chianti La Pruneta, Michelangelo apartment

Guest favourite

Condo in Monte San Savino

4.97 out of 5 average rating, 36 reviews

Farmhouse Tuscany | Terrace, pool & restaurant

Guest favourite

Condo in San Gimignano

4.95 out of 5 average rating, 118 reviews

Adalberto Apartment inside the Manor of Fulignano

Guest favourite

Condo in Cinigiano

5 out of 5 average rating, 71 reviews

Spinosa Apartment in Podere Capraia

Guest favourite

Condo in Montieri

5 out of 5 average rating, 40 reviews

PodereCupiano "la Costa"

Guest favourite

Condo in CORTONA

4.96 out of 5 average rating, 24 reviews

Relaxation and peace in the countryside Cortona G

Guest favourite

Condo in Cortona

5 out of 5 average rating, 29 reviews

4 pers. apartment with big terrace at Cortona

Guest favourite

Condo in Castelnuovo Berardenga

4.97 out of 5 average rating, 60 reviews

Castello di Orgiale Charme Residenz

Home rentals with a private pool

Guest favourite

Villa in Castiglion d'orcia

4.97 out of 5 average rating, 98 reviews

Old Hamlet Vignalunga

Guest favourite

Home in San Casciano in Val di pesa

4.82 out of 5 average rating, 85 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Guest favourite

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 182 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Guest favourite

Home in Civitella Paganico (GR)

4.94 out of 5 average rating, 18 reviews

Podere Vignali by Interhome

Guest favourite

Home in Pergaccio

5 out of 5 average rating, 45 reviews

Villa Pergo is an ancient charming country villa

Guest favourite

Home in Civitella in Val di Chiana

5 out of 5 average rating, 11 reviews

Casa Clotilde by Interhome

Guest favourite

Home in Cortona

4.92 out of 5 average rating, 13 reviews

Il Loto by Interhome

Guest favourite

Home in San Casciano in Val di pesa

5 out of 5 average rating, 35 reviews

Charming villa with pool in the Chianti hills

Quick stats about holiday rentals with a pool in Montepulciano

Total rentals
20 properties
Nightly prices starting at
$72 AUD before taxes and fees
Total number of reviews
460 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Wi-Fi availability
20 properties include access to Wi-Fi

Destinations to explore