
Holiday rentals with a pool in Montalcino
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Montalcino
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

EcoLodge – modernes Design in ruhiger Panoramalage
Die EcoLodge, modern, ökologisch, komfortabel, liegt mitten in der Natur in einer friedlichen, fruchtbaren Kulturlandschaft am Monte Amiata in der stillen Südtoskana. Sie gehört zu einem alten Bauernhaus mit viel Platz, wunderschöner Aussicht, vielen alten Obst-, Marroni-, Olivenbäumen und unserem Weinberg. Es ist ein idealer Standort. Von hier aus können Sie weltberühmte Sehenswürdigkeiten erkunden, viel unternehmen und abseits der Touristenströme die Ruhe des toskanischen Landlebens genießen.

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.

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.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

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.

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.

Relax e charme tra le colline del chianti
Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

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.

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) * 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.

Appaloosa - Apartment for couples and families
Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Interno Italiano

Casolare immerso nella natura

Infinity pool in Chianti

Private Chianti Cottage, Garden & Vineyard Views

Borgo Ripostena – n. 5 Rimessa

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

La Casa di Nada Home

Country House in the Crete Senesi
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment

Appartamento Loggiato 3 in toscana vicino Siena

Fattoria Lornano Winery- villa ''Trebbiano''

Scenic Stilish Country

💜 "Gaia" Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Residenza Vintage con Piscina nel Chianti

Castello di Orgiale Charme Residenz
Home rentals with a private pool

Podere Molinaccio-Luxury Tuscan-style Eco Villa

Villa il Palagio nelle campagne toscane

Suite Casa Luigi con piscina esclusiva

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa

TREEhouse/casaBARTHEL

Esplora la natura al centro di Vigneti Chianti
Historic villa x8 with exclusive pool
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £198 | £176 | £180 | £158 | £167 | £178 | £192 | £207 | £182 | £174 | £193 | £197 |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about holiday rentals with a pool in Montalcino

Total holiday rentals
Explore 400 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 8,470 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 250 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
390 of Montalcino holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Montalcino rentals

4.8 Average rating
Montalcino stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Flat rentals Montalcino
- Rentals with a fireplace Montalcino
- Rentals with an EV charger Montalcino
- Hotel rooms Montalcino
- Luxury rentals Montalcino
- Rentals with outdoor seating Montalcino
- Cottage rentals Montalcino
- Bed and breakfasts Montalcino
- House rentals Montalcino
- Rentals with a hot tub Montalcino
- Rentals with a patio Montalcino
- Smoking-friendly rentals Montalcino
- Rentals with a firepit Montalcino
- Farm stay rentals Montalcino
- Rentals with a washing machine and dryer Montalcino
- Family-friendly rentals Montalcino
- Fitness-friendly rentals Montalcino
- Rentals with a sauna Montalcino
- Apartment rentals Montalcino
- Holiday home rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Feniglia
- Del Chianti
- Centro Storico Orvieto
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Palazzo Pubblico
- CavallinoMatto
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Terme San Filippo
- Casa Vasari
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Monte Oliveto Maggiore
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Food and drink Siena
- Sports activities Siena
- Art and culture Siena
- Tours Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Sports activities Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Things to do Italy
- Entertainment Italy
- Food and drink Italy
- Art and culture Italy
- Wellness Italy
- Tours Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy







