Family-friendly vacation rentals in Montepulciano

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Top-rated family-friendly rentals in Montepulciano

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Guest favourite

Farm stay in Montepulciano

4.96 out of 5 average rating, 136 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.

Mar. 7 – 14

$135 CAD per night

Guest favourite

Apartment in Siena

4.99 out of 5 average rating, 136 reviews

Villa di Geggiano - Alfieri Suite

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Apr. 18 – 25

$618 CAD per night

Guest favourite

Apartment in Montepulciano

4.97 out of 5 average rating, 331 reviews

A view from the top

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2024 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Jan. 11 – 18

$222 CAD per night

Guest favourite

Apartment in Montepulciano

4.96 out of 5 average rating, 136 reviews

Stuart Black Tea Amazing View & Super Central

This apartment is in a prime central location and enhanced by an abundance of natural light and awe-inspiring panoramic vistas. Its advantageous proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Additionally, guests will have access to a sun-drenched backyard garden terrace, creating an ideal setting for savouring a glass of wine. Kindly be informed that the open fireplace is purely ornamental in nature.

Nov. 3 – 10

$185 CAD per night

Guest favourite

Farm stay in Seggiano

4.98 out of 5 average rating, 194 reviews

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Dec. 12 – 19

$152 CAD per night

Guest favourite

Apartment in Laviano

4.95 out of 5 average rating, 100 reviews

Farmhouse with swimming pool with wonderful view

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests eight vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

Apr. 23 – 30

$209 CAD per night

Guest favourite

Apartment in Montepulciano

4.99 out of 5 average rating, 220 reviews

Montepulciano Downtown Storico

Nice apartment of 60 square meters located in the main street of the country. It is on the second and top floor of a historic building. The entrance is located on the main street of the town while the windows face the outside of the walls offering breathtaking views. The apartment consists of: entrance, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. Microwave, large oven, dishwasher, washing machine, and wi-fi.

Apr. 8 – 15

$125 CAD per night

Guest favourite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 311 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Nov. 30 – Dec. 7

$219 CAD per night

Guest favourite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 238 reviews

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Apr. 21 – 28

$214 CAD per night

Guest favourite

Apartment in Montepulciano

4.96 out of 5 average rating, 209 reviews

Casa Ricci Apartment in palazzo del 1300

Our apartment is located a few meters from Piazza Grande, can accommodate up to 4 people and overlooks an evocative panorama .It has been recently renovated and is located in a historic building from 1300. Our apartment is located a few meters from Piazza Grande, it sleeps up to 4 people and overlooks a beautiful. Was recently renovated and is located in a historic building in 1300.

Jan. 5 – 12

$160 CAD per night

Guest favourite

Apartment in Monticchiello

4.99 out of 5 average rating, 299 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

Apr. 17 – 24

$350 CAD per night

Guest favourite

Farm stay in Pari

4.98 out of 5 average rating, 225 reviews

TUSCANY farm house SWIMMING POOL

Our little farm is a beautiful location for a relaxing vacation with a private swimming pool. We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

Apr. 23 – 30

$147 CAD per night