
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 $85 NZD per night before taxes and fees

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Over 7,800 verified reviews to help you choose

Pet-friendly accommodation
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

Wi-Fi availability
140 of Montepulciano holiday rentals include Wi-Fi 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.

Montepulciano Central Villa - Sauna & Jacuzzi
Self checkin Get used to the Italian country lifestyle in this renovated, classic home. Turn on the fireplace to warm up in evenings or take a dip in the JACUZZI after an excursion. Maybe even invite friends for a nice dinner and then an evening SAUNA session. AIR CONDITIONER in each room In the heart of the historic center of Montepulciano, a stone's throw from Piazza Grande, we offer a unique and prestigious building of about 250 square meters. The unit is spread over three levels above ground with a splendid cave with shower and sauna in the basement. LOCATION: The building has an independent entrance, and is located in one of the most beautiful and evocative streets in all of Montepulciano. Montepulciano stands on the ridge that divides the Val d'Orcia from the Val di Chiana, and is located on a limestone hill. This beautiful Renaissance village, with a medieval layout, is set in a postcard landscape, which in any direction you look at refers to the most classic and widespread idea of the Tuscan countryside, the one where waves of hills and golden fields dotted with cypresses chase each other. The Montepulciano area, with its excellent vineyards, is considered one of the best wine regions in the world and is certainly one of the most loved and visited tourist destinations in Tuscany Accesso autonomo con chiave in locker fuori al portone ( a richiesta ). Palazzetto nel centro storico interamente e finemente ristrutturato. Potrai accendere il camino durante le fredde serate, fare una SAUNA oppure immergerti nella JACUZZI Le camere hanno ARIA CONDIZIONATA The house 'was renovated with details of great luxury. You can turn on the fireplace to warm your evenings or take a jacuzzi tub on your return from your excursions or even find a moment to relax in the sauna together with your friends or relatives Nearby the famous spas of Chianciano, the charming and romantic Pienza, the surreal little town of Bagni Vignone with thermal water pools, Monticchiello where you step back in time and then Siena, Montalcino, San Gimignano, Cortona and Arezzo yet Florence ....... and all the beautiful Tuscany around you! The house is built on several levels. On the ground floor a large living room with fireplace, the spacious fully equipped kitchen, laundry room and a bathroom. The first-floor suite with a private bathroom and the second double room with bathroom. Even more on the attic floor with 2 other beds and small bathroom. In the basement, cellar compartment with showers and sauna. Guests will have the whole house I will be at your disposal for any request ..... There is no place more evocative in Tuscany, this charming village of Chianti, situated on a hill high m.650, rich in vineyards and ancient cellars. Nearby the famous spas of Chianciano, the charming and romantic Pienza, the surreal little town of Bagni Vignone with thermal water pools, Monticchiello where you step back in time and then Siena, Montalcino, San Gimignano, Cortona and Arezzo yet Florence ....... and all the beautiful Tuscany around you! The church of San Biagio, the Dome of Montepulciano, pound shops with local crafts ...... if you look for handmade things ..... you'll be in the right place! :-) The house is very large and articulated on four levels. In the basement there are sauna (for 3/4 people) and a shower. In the ground floor, the living room with dining table and living room with fireplace and TV, large kitchen, laundry room and a bathroom. On the first floor, the master bedroom with private bath and jacuzzi and double room with bathroom and shower, on the top floor there is a master bedroom, and a loft with sofa bed and pullout bed. Experience Montepulciano's small town magic with quaint food and drink options. Feel transported back to the 1500s, while exploring secret basements, old convents with vaulted ceilings, or ancient excavations, which can be found all over town. Montepulciano, once again this year, is ready to host all visitors who want to fully experience in the magical local atmosphere. Don’t forget a romantic walk through the streets of the charming historic center, the glimpses of the Val d'Orcia and the extraordinary excellences. food and wine of the area: pici, Tuscan and Cinta Senese salami, tagliata and Florentine di Chianina, pecorino cheese, typical pasta to be enjoyed with traditional sauces and of course the Vino Nobile di Montepulciano DOCG. Of note is the Civic Museum which since 1954 has been based in Via Ricci, in the fourteenth-century Palazzo Neri Orselli. Various cultural initiatives are held in this evocative location and recently the attribution to Caravaggio of a portrait from the collection has aroused strong interest in this museum. For those who stop for several days in Montepulciano, within 30 minutes by car there is no shortage of extraordinary places to visit such as the cities of Pienza and Cortona, Sarteano and the Etruscan Museum of Chiusi, the medieval villages of Montefollonico, Bagno Vignoni and Monticchiello. And among the Sienese hills of Sant’Albino, about 3 km from Montepulciano, are the Terme di Montepulciano, a modern health, wellness and beauty center characterized by the exclusivity of the thermal waters that flow from over 130 meters deep. With your car, you can comfortably in less than 40 minutes, reach multiple sites and charming locality of Tuscany if you have small children, is also the high chair and cot for baby
Indoor spacesFamilyValue
4.85 out of 5 average rating, 153 reviews
Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
FamilyIndoor spacesLaundry
4.92 out of 5 average rating, 620 reviews
Amazing Apartment near Piazza Grande w/ Terrace
Welcome to the heart of Montepulciano, one of Tuscany’s most iconic, captivating, and historic towns, renowned for its Renaissance palazzos, ancient wine cellars, and timeless atmosphere that enchants every traveler. Our apartment is located in an incredible spot right in the historic center, just a short walk from Piazza Grande, excellent restaurants, local shops, and the town's most authentic treasures. Whether you're here to taste exceptional wines or enjoy a romantic getaway, we're here for you.
FamilyIndoor spacesLocation
4.92 out of 5 average rating, 186 reviews
Wine Experience Villa in Montepulciano
🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.
Indoor spacesFamilyCondition
4.97 out of 5 average rating, 125 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.
KitchenIndoor spacesCleanliness
4.97 out of 5 average rating, 246 reviews
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
Indoor spacesKitchenCleanliness
4.98 out of 5 average rating, 163 reviews
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.
KitchenIndoor spacesWalkability
4.99 out of 5 average rating, 177 reviews
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
Indoor spacesFamilyBreakfast
4.92 out of 5 average rating, 331 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.
FamilyIndoor spacesBarbecue
4.94 out of 5 average rating, 107 reviewsLa 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.
Indoor spacesFamilyBathroom
5.0 out of 5 average rating, 510 reviews
Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
Indoor spacesKitchenCheckout
4.97 out of 5 average rating, 158 reviews
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.
Indoor spacesKitchenCondition
4.91 out of 5 average rating, 304 reviewsPopular amenities for Montepulciano family-friendly rentals
Family-friendly home rentals with a hot tub

Charming Tuscan Villa with View forFamily&Friends
Indoor spacesFamilyCheck-in
4.97 out of 5 average rating, 128 reviews
Casa al Gianni - The Simignano Barn
Indoor spacesFamilyOutdoor spaces
4.97 out of 5 average rating, 194 reviews
Villa in Montepulciano with a Pool
Indoor spacesKitchenLong stay
4.92 out of 5 average rating, 146 reviews
Palazzo Monaci - Pool in the Crete Senesi
KitchenFamilyDecor
4.96 out of 5 average rating, 138 reviews
Villa unesco heritage, Jacuzzi & garden. BB Daria
Indoor spacesFamilyCleanliness
4.98 out of 5 average rating, 182 reviewsWp Relais Villa Vignalunga
KitchenIndoor spacesAmenities
4.93 out of 5 average rating, 116 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Indoor spacesFamilyHot tub
4.99 out of 5 average rating, 113 reviews
Poggio dell'orso.Traditional Casale. Amazing views
KitchenIndoor spacesDecor
4.96 out of 5 average rating, 167 reviewsFamily- and pet-friendly home rentals

Agriturismo Pescaia Montepulciano Apartment 2
Indoor spacesFamilyBathroom
4.97 out of 5 average rating, 166 reviews
In Tuscany Rooms
KitchenFamilyHospitality
4.96 out of 5 average rating, 137 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
FamilyKitchenTV
4.95 out of 5 average rating, 102 reviews
Separate room, between Cortona and Montepulciano
FamilyIndoor spacesBathroom
4.95 out of 5 average rating, 226 reviews
HOLIDAY APARTMENT IN HISTORICAL PALACE- MARINA
FamilyIndoor spacesLayout
4.94 out of 5 average rating, 218 reviews
Casa Bonari - a paradise for the eyes
KitchenIndoor spacesComfort
4.97 out of 5 average rating, 187 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
FamilyKitchenAccuracy
5.0 out of 5 average rating, 115 reviews
Palazzi del Papa Farmhouse in Val d'Orcia, Pienza
FamilyIndoor spacesShared spaces
4.94 out of 5 average rating, 194 reviewsFamily-friendly home rentals with a pool

Castel Brunello - 2 doublebed rooms + terrace
FamilyKitchenBiking
4.99 out of 5 average rating, 117 reviews
Spedaletto Castle, Val d'Orcia, Pienza
Indoor spacesKitchenPool
4.97 out of 5 average rating, 181 reviews
Conca d'Oro villa with private pool, sleeps 4
Indoor spacesFamilySleep quality
4.92 out of 5 average rating, 172 reviews
Romantic apartment in a quite place
FamilyIndoor spacesLong stay
4.93 out of 5 average rating, 172 reviews
Mimosa Apartment - Poggio al Vento
FamilyKitchenGetting around
4.99 out of 5 average rating, 112 reviews
Farmhouse close to Montepulciano
Indoor spacesFamilyCheck-in
4.94 out of 5 average rating, 156 reviews
La Casa delle Querce - "Belvedere" (The House of Oaks - "Belvedere")
Indoor spacesKitchenDecor
4.85 out of 5 average rating, 113 reviews
Piandimaggio family and friends
FamilyIndoor spacesShared spaces
4.87 out of 5 average rating, 322 reviewsWhen is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $277 NZD | $256 NZD | $270 NZD | $278 NZD | $297 NZD | $277 NZD | $283 NZD | $300 NZD | $299 NZD | $280 NZD | $283 NZD | $294 NZD |
| 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 |
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- 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
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