
Family-friendly holiday rentals in Montepulciano
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Montepulciano

Total holiday rentals
Explore 130 holiday rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 7,520 verified reviews to help you choose

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
130 of Montepulciano holiday rentals include wifi access

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

4.9 Average rating
Montepulciano stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated family-friendly rentals in Montepulciano
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

The walnut tree view, Montepulciano
The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

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.

Casa Dolce Toscana | Panoramic Suites & Views
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

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.

Stuart White Tea Central Panoramic & Garden
Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.
La Piazzetta - Cozy open space in the historic center of Montepulciano
Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Casa al Gianni - Oak
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

I Tramonti di Eramo, downtown Montepulciano.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Casa Ricci Apartment in a 14th-century building
Our apartment is located a few meters from Piazza Grande, sleeps up to 4 people and overlooks a beautiful view. It was recently renovated and is located in a historic building from the 1300s. Our apartment is located a few meters from Piazza Grande, it sleeps up to 4 people and overlooks a beautiful view. It was recently renovated and is located in a historic building from the 1300s.

Tuscany on the terrace, downtown Montepulciano
Welcome to Montepulciano, the hidden gem of Tuscany, where historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region.
Wp Relais Villa Vignalunga
Come with WP Relais to discover Villa Vignalunga in the Val d'Orcia: a luxurious estate with swimming pool, spacious rooms and breathtaking views. Book now for a unique experience in Tuscany.
Popular amenities for Montepulciano family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Villa in Montepulciano with a Pool

Tuscan Villa - Montepulciano

Villa di Geggiano - Perellino Suite

Charming House in Montepulciano

Fontarcella, H&R- mediterranean home with jacuzzi

Villa unesco heritage, Jacuzzi & garden. BB Daria
Family- and pet-friendly home rentals

Beautiful medieval village!!!

Farmhouse on a winery

Mascagni Farmhouse in Val d'Orcia, Pienza

Magnificent 2 BR with Terrace and Air Conditioning

il poderuccio farmhouse studio apartment

La Casa delle Querce - "Policiano" (The House of Oaks - "Policiano")

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza

Poggio Bicchieri Holiday Farm - Memoria apartment
Family-friendly home rentals with a pool

Private Tuscan Villa with Pool - Montepulciano

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Il nido del Rondone

Casa Crociani - Amazing Pool & Free Parking

La Rimbecca Farmhouse, Gli Archi

Biancospino

Casa Tondino | Ground floor 2-bedroom apartment (4

Casa Luigi Suite with exclusive pool
When is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $209 SGD | $194 SGD | $204 SGD | $195 SGD | $204 SGD | $208 SGD | $214 SGD | $227 SGD | $226 SGD | $212 SGD | $214 SGD | $222 SGD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Pet-friendly rentals Montepulciano
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- Rentals with a hot tub Montepulciano
- Villa rentals Montepulciano
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- Rentals with pools Montepulciano
- House rentals Montepulciano
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- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Centro Storico Orvieto
- Basilica of St Francis
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Cascate del Mulino
- Mount Subasio
- Siena Cathedral
- Parco Regionale Della Maremma
- Palazzo Pubblico
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Terme San Filippo
- Eremo Di Camaldoli
- Casa Vasari
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Monte Oliveto Maggiore
- Things to do Montepulciano
- Food and drink Montepulciano
- Things to do Siena
- Sports activities Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Art and culture Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Entertainment Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Things to do Italy
- Entertainment Italy
- Food and drink Italy
- Wellness Italy
- Nature and outdoors Italy
- Art and culture Italy
- Sightseeing Italy
- Tours Italy
- Sports activities Italy







