
Family-friendly holiday rentals in Massa Marittima
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Massa Marittima
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Pieve di Caminino Historic Farm
Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due 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.

House with a breathless view in Tuscany
Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Terra Delle Sidhe, Seggiano, Tuscany, Italy
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.

Casa Vecchio Forno
The apartment is on the ground floor, in the historic center of Massa Marittima, just 100 meters from the Cathedral square. It is easily accessible from all the parking lots in the historic center and within walking distance you can find: cafes, restaurants, banks, grocery stores, a pastry shop and a pharmacy. The recently renovated 68m house has a separate entrance and consists of: a kitchen with kitchenette, a double bedroom, a living room with sofa bed and a bathroom.

Sunset on Chianti Classico
If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

Casa Sabina
The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Casa del Poggio, with a beautiful sea view
The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

TOWER apartment in small castle near Florence
Romantic, Historically unique, Magical atmosphere, 360 degree views of the countryside and Florence. Great retreat for digital nomads, or simply to retreat from the hustle and bustle. Convenient for Chianti and Tuscany explorations. A/C in 2 rooms. Cooking class and wine tasting available. If you'd like to add more space and comfort, book the TOWER PENTHOUSE: double the space, a large kitchen, another bathroom. Perfect for families!

Leo's porch
Stay in this unique place and spend unforgettable evenings gazing at the horizon. Breathe clean air and enjoy the relaxation offered by the village of Scarlino. Ideal for couples or small families who want functional and comfortable accommodation. FROM MAY 1 TO AUGUST 31, a tourist tax of €1.00 per night/person is applied for each day of stay. Bed linen and towels are NOT INCLUDED in the final price of the accommodation.

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!
Popular amenities for Massa Marittima family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

Amazing Tuscany Villa, FREE parking

San Giovanni in Poggio, villa Meriggio 95mq

Beautiful renovated barn in Tuscany

Agriturismo La Villa - L'Olivo, Pool & Hot Tub

Il Fienile di Tigliano (former barn in Vinci-Florence)

Your Private Tuscan Retreat

Villa di Geggiano – Guesthouse
Family- and pet-friendly home rentals

Belforti Tower

Beautiful medieval village!!!

country villa with heated swimming pool

Holiday in antique farm, Belvedere

Antico Borgo Ripostena – n. 8 Old House

Countryside Cottage With View - Le Rondini apt

Secret Garden Siena

Tuscan Cottage with swimming pool Pet Friendly
Family-friendly home rentals with a pool

Tenuta Chiudendone in Tuscany

Loggiato 3 apartment in Tuscany near Siena

Infinity pool in Chianti area

Cercis - La Palmierina

Podere La Castellina - No. 1 COTTAGE

Spinosa Apartment in Podere Capraia

Countryside Dream farm in Tuscany

Manuela apartment with pool in farmhouse
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $117 SGD | $109 SGD | $131 SGD | $136 SGD | $137 SGD | $140 SGD | $142 SGD | $187 SGD | $150 SGD | $132 SGD | $128 SGD | $117 SGD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about holiday rentals that are family-friendly in Massa Marittima

Total holiday rentals
Explore 40 holiday rentals in Massa Marittima

Nightly prices starting at
Massa Marittima holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 760 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Massa Marittima holiday rentals include wifi access

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

4.7 Average rating
Massa Marittima stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- House rentals Massa Marittima
- Smoking-friendly rentals Massa Marittima
- Rentals with outdoor seating Massa Marittima
- Chalet rentals Massa Marittima
- Villa rentals Massa Marittima
- Rentals with a washing machine and dryer Massa Marittima
- Rentals with a patio Massa Marittima
- Rentals with breakfast Massa Marittima
- Rentals with a fireplace Massa Marittima
- Pet-friendly rentals Massa Marittima
- Apartment rentals Massa Marittima
- Flat rentals Massa Marittima
- Family-friendly rentals Grosseto
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Elba
- Giglio Island
- Spiagge Bianche
- Feniglia
- Cala Violina
- Gulf of Baratti
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Libera
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Spiaggia Marina di Cecina
- Cala di Forno
- Spiaggia di Marina di Campo
- Zuccale Beach
- Castiglion del Bosco Winery
- Spiaggia di Patresi
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Cavo
- Spiaggia di Marina di Grosseto
- Spiaggia Verruca




