
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 140 holiday rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $63 SGD per night before taxes and fees

Verified guest reviews
Over 7,800 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
70 properties have a dedicated workspace

Wifi availability
140 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.

Agriturismo Poggio Bicchieri ap. Memoria
Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!
KitchenFamilyNearby

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.
KitchenFamilyPool

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.
Indoor spacesKitchenPets

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away
FamilyKitchenCheckout

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
KitchenIndoor spacesLocation

Montepulciano Centro Storico
Grazioso appartamento di 60 mq situato nel corso principale del paese. Si trova al secondo ed ultimo piano di un palazzo storico. L'ingresso è situato sul corso principale della cittadina mentre le finestre si affacciano verso l'esterno delle mura offrendo un vista mozzafiato. L'appartamento è composto da: ingresso, soggiorno con divano letto matrimoniale, camera da letto, cucina, bagno con finestra a tetto. E' dotato di forno a microonde, forno grande, lavastoviglie, lavatrice e wi-fi.
FamilyIndoor spacesAccuracy

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.
KitchenIndoor spacesOutdoor spaces

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.
KitchenFamilyBreakfast
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla 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, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.
KitchenFamilyBiking

Casale in pietra in Val D’Orcia
Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.
FamilyIndoor spacesHeating

I Tramonti di Eramo, Montepulciano centro.
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.
KitchenFamilyWalkability

Dimora dell'Erbe - Rooftop Apartment
The apartment has two independent double bedrooms with private bathroom (Nepitella and Timo), a large bright kitchen with living room and finally exclusive access to the beautiful terraces that overlook the roofs of Montepulciano. The modern and functional kitchen offers an induction hob, dishwasher fridge and a service for 6 people. Independent air conditioning and heating and wi-fi.
Indoor spacesKitchenBreakfast
Popular amenities for Montepulciano family-friendly rentals
Family-friendly home rentals with a hot tub

Montepulciano Central Villa – Sauna & Jacuzzi
KitchenIndoor spacesCheckout

Villa a Montepulciano con Piscina
FamilyIndoor spacesWifi

Charming Tuscan Villa with View forFamily&Friends
FamilyIndoor spacesLocation

Casa al Gianni - Il Fienile di Simignano
KitchenFamilyCleanliness

Wp Relais Borgo Vignalunga
Indoor spacesFamilyGrill

Casa Dolce Toscana | Panoramic Suite & View
KitchenFamilyWalkability

Palazzo Monaci - Piscina nelle crete Senesi
FamilyKitchenParking

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

A paradise in Montepulciano...
Indoor spacesKitchenSleep quality

In Toscana Camere
FamilyKitchenBiking

Unique view 3 bdr villa with pool & A/C in Pienza
FamilyIndoor spacesNearby

Your Tuscan oak tree house, enchanting Val d'Orcia
FamilyIndoor spacesAccuracy

Agriturismo Pescaia Montepulciano Appartamento 2
FamilyIndoor spacesPets

Casa rurale toscana in Mascagni Farmhouse Pienza
Indoor spacesFamilyCheck-in

Casa Bonari - un paradiso per gli occhi
FamilyKitchenBreakfast

Amazing Apartment near Piazza Grande w/ Terrace
FamilyKitchenCheck-in
Family-friendly home rentals with a pool

Conca d'Oro villa with private pool, sleeps 4
Indoor spacesKitchenOutdoor spaces

Castello di Spedaletto, Val d'Orcia, Pienza
KitchenIndoor spacesGetting around

Appartamento Mimosa - Poggio al Vento
KitchenFamilyOutdoor spaces

Castel Brunello - 2 doublebed rooms + terrace
FamilyKitchenQuiet

Romantic apartment in a quite place
Indoor spacesKitchenDecor

Farmhouse close to Montepulciano
Indoor spacesKitchenBreakfast

Panoramic Country Suite Montalcino
KitchenFamilyParking

Tuscan Barn Apartment for 6 with panoramic pool
FamilyIndoor spacesLong stay
When is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $207 SGD | $191 SGD | $202 SGD | $208 SGD | $222 SGD | $207 SGD | $212 SGD | $224 SGD | $223 SGD | $209 SGD | $212 SGD | $219 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
- Bed and breakfasts Montepulciano
- Pet-friendly rentals Montepulciano
- Rentals with breakfast Montepulciano
- Villa rentals Montepulciano
- Apartment rentals Montepulciano
- Cottage rentals Montepulciano
- House rentals Montepulciano
- Flat rentals Montepulciano
- Rentals with pools Montepulciano
- Rentals with a hot tub Montepulciano
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals 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
- Eremo Di Camaldoli
- La Scarzuola
- Antinori nel Chianti Classico
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- Vulci
- 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
- Rocca Maggiore
- Things to do Montepulciano
- Tastings Montepulciano
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Workouts Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







