
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 $175 NZD per night before taxes and fees

Verified guest reviews
Over 620 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
20 of Montepulciano holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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.

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.
4.96 out of 5 average rating, 142 reviews
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.
4.97 out of 5 average rating, 126 reviews
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.
4.97 out of 5 average rating, 252 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.
4.95 out of 5 average rating, 229 reviews
L'Aquila e L'Ulivo
All'Aquila e l'Ulivo, un antico casale ristrutturato del 1200, troverai non solo tutti i confort necessari per uno splendido soggiorno, ma vivrai anche l'emozione di sentirti libero e immerso nella natura incontaminata della Val D'Orcia. Qui avrai la possibilita' di passeggiare con i due falchi Ayga e Sayen e interagire con le aquile, e perchè non sorseggiare un eccellente aperitivo a bordo piscina. Ti aspettiamo nel nostro mondo, fatto di animali, relax, natura e anche un pizzico di Magia.
5.0 out of 5 average rating, 129 reviews
Villa a Montepulciano con Piscina
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) * 2 AirCon units: 1 per bedroom * * 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. *
4.92 out of 5 average rating, 149 reviews
Tuscan farmhouse stay with restaurant and pool
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.
4.94 out of 5 average rating, 109 reviews
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.
4.96 out of 5 average rating, 169 reviews
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.
4.93 out of 5 average rating, 130 reviews
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
4.92 out of 5 average rating, 173 reviews
Castello di Spedaletto, Val d'Orcia, Pienza
L'agriturismo Castello di Spedaletto sorge nell’edificio che un tempo ospitava il granaio dell’antico castello medioevale ed è stato recentemente ristrutturato in perfetto equilibrio tra modernità e tradizione: pietra, mattoni, travi a vista si fondono con la caratteristica scalinata in cristallo e ferro battuto. L'agriturismo è formato da 5 camere matrimoniali con bagno e 2 appartamenti. Vieni, Vedi, Vivi…
4.97 out of 5 average rating, 185 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.
4.95 out of 5 average rating, 104 reviewsPopular amenities for Montepulciano rentals with a pool
House rentals with a pool

Casa Rosmarino Eco-Wellness Country Home
4.99 out of 5 average rating, 274 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
4.98 out of 5 average rating, 145 reviews
Casolare immerso nella natura
4.99 out of 5 average rating, 111 reviews
PoggiodoroLoft, Tuscan dream e relax
4.87 out of 5 average rating, 167 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 125 reviews
Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 138 reviews
Infinity pool in Chianti 1
5.0 out of 5 average rating, 143 reviews
La Lisa: country house surrounded by fields
4.94 out of 5 average rating, 135 reviewsCondo rentals with a pool

Storica villa del 1600 nel Chianti in Toscana
5.0 out of 5 average rating, 223 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Relax Tra Le Vigne Del Chianti-IlVillinoFarmhouse
4.81 out of 5 average rating, 366 reviews
Apt.Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Casa Granaio | Ground floor 1-bedroom apartment (2
4.96 out of 5 average rating, 82 reviews
Borgo 7 Tigli | King Suite & Tuscan Views
4.67 out of 5 average rating, 3 reviews
Tuscan Dream Apt with Pool, View & Tennis Court
4.91 out of 5 average rating, 97 reviewsHome rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
Esplora la natura al centro di Vigneti Chianti
4.97 out of 5 average rating, 265 reviews
Suite Casa Luigi con piscina esclusiva
4.95 out of 5 average rating, 122 reviews
Villa Pergo is an ancient charming country villa
5.0 out of 5 average rating, 66 reviews
Podere Molinaccio-Luxury Tuscan-style Eco Villa
4.93 out of 5 average rating, 27 reviewsDestinations to explore
- Bed and breakfasts Montepulciano
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- Rentals with a hot tub Montepulciano
- 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
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- La Scarzuola
- Eremo Di Camaldoli
- Antinori nel Chianti Classico
- Siena Cathedral
- Vulci
- Avignonesi Winery Fattoria Le Capezzine
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Saturnia Thermal Park
- Valdichiana Outlet Village
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Piazza del Campo
- Things to do Montepulciano
- Tastings Montepulciano
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Dining Siena
- Food tours Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Workouts Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Wildlife Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Art workshops Tuscany
- Shopping and fashion Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Performances Italy
- Museums Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







