Family-friendly vacation rentals in Massa Marittima

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Top-rated family-friendly rentals in Massa Marittima

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Guest favorite

Loft in Massa Marittima

4.88 out of 5 average rating, 155 reviews

Authentic Cave House in the heart of the Village!

The house is in the heart of Massa Marittima, a medieval village which is setting on the top of a hill in the Maremma countryside. This authentic historical small town is short driving distance from many amazing beaches of the Mediterranean coast: Cala Violina, Torre Mozza, the Baratti Etruscan Riviera.. Ideal for a romantic escape but also for those who are looking for a local experience in a relaxed, suggestive, historical context far away from mass tourist routes. PLEASE READ ALL DESCRIPTION!

Oct 9 – 16

G$22,022 GYD per night

Guest favorite

Home in Peccioli

4.99 out of 5 average rating, 113 reviews

A breathless view

Placed halfroad between Florence and Pisa this Airbnb has a large terrace and a hanging garden. All of this is set against a backdrop of endless hills. It is like a living and eternal painting, where one is not a spectator but an actor and part of a film scene. Being North East here every morning the sun appears on the horizon behind the last strip of green hills while white brushstrokes of mist melt into the air as the red ball rises into the sky. It is a sight that takes one's breath away.

Dec 7 – 14

G$32,440 GYD per night

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 109 reviews

Villa di Geggiano - Guesthouse

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.

Nov 7 – 14

G$123,611 GYD per night

Guest favorite

Home in Vaiano

5.0 out of 5 average rating, 201 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients, such as bio vegetables, eggs or cheese.

Mar 24 – 31

G$35,279 GYD per night

Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 333 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 19 – 26

G$33,361 GYD per night

Guest favorite

Apartment in Caminino

4.92 out of 5 average rating, 131 reviews

Pieve di Caminino Historic Farm

L'antica fattoria Pieve di Caminino, oggi biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due antiche strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Apr 26 – May 3

G$32,414 GYD per night

Guest favorite

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.

Apr 27 – May 4

G$23,352 GYD per night

Guest favorite

Condo in Massa Marittima

4.99 out of 5 average rating, 155 reviews

Casa Vecchio Forno

The apartment is on the ground floor, in the historic center of Massa Marittima, just 100 meters from Piazza del Duomo. It is easily accessible from all the car parks of the historic center and within walking distance you can find: bars, restaurants, banks, groceries, a pastry shop and a pharmacy. The house recently renovated, has a separate entrance and consists of: a kitchen with kitchenette, a double bedroom, a living room with sofa bed and a bathroom.

Feb 14 – 21

G$17,321 GYD per night

Guest favorite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 242 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 3 – 10

G$31,706 GYD per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 310 reviews

Old hayloft on the Chianti hills

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. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Dec 13 – 20

G$33,256 GYD per night

Guest favorite

Villa in Ambra

4.98 out of 5 average rating, 108 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Villa with 5bedrooms and 10sleeps in Chianti . Land of wine, good food and old traditions. Distances from the villa to:Siena 25km,Arezzo 35km,Florence 60km,villa with swimming pool obtained from the careful restoration of an ancient stone farmhouse

Feb 4 – 11

G$173,670 GYD per night

Guest favorite

Apartment in Monticchiello

4.99 out of 5 average rating, 300 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 ...

Nov 1 – 8

G$50,438 GYD per night