
Family-friendly holiday rentals in Massa Marittima
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Top-rated family-friendly rentals in Massa Marittima
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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!

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

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!

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.

Captain's House | Monte Grosso, Elba
The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Casa Dolce Toscana | Panoramic Suite with a View
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.

Design apartment in Massa Marittima, "slow city"
A great 65 m2 - 2 bedroom Apartment, entirely renovated in freestone and exposed beams, with design touch. In the upper, medieval part of Massa Marittima, Siena in miniature, with a superb Romanesque cathedral. Central but quiet area. Many restaurants and oeno-gastronomic specialties. Magnificent freshwater lake, Lago dell'Accesa, 10 minutes by car. Sea at 20 minutes. Siena at 1:15 a.m. Massa, "Citta slow", offers many other activities: museums, wine cellars, horse riding, Bike Park, MTB

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.

Casa al Gianni - Hut
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Suite in Castello di Valle
A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.
Popular amenities for Massa Marittima family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

White lily with a view of Siena

Torretta Apartment

Villa di Geggiano – Guesthouse

Villa unesco heritage, Jacuzzi & garden. BB Daria

Green Dome @ The Land Before Time Retreats

La Casetta

Typical Tuscan country house
Family- and pet-friendly home rentals

The Eagle and the Olive Tree

Stone farmhouse in Val D'Orcia

Borgo Ripostena – No. 5 Garage

country villa with heated swimming pool

Costalmandorlo, a rustic home in the heart of Tuscany

Casa Al Poggio & Chianti view

In Tuscany Rooms

Typical Tuscan Country House WITH A/C
Family-friendly home rentals with a pool

Tenuta Chiudendone in Tuscany

Penthouse with pool view a few km from Follonica

Design loft with private SPA in Tuscany

Belforti Tower

Stone House with Exclusive Pool Codilungo in Chianti

Farmhouse on a winery

Podere La Castellina - No. 3 JUNIPER

Countryside Dream farm in Tuscany
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £83 | £83 | £84 | £79 | £80 | £81 | £83 | £109 | £87 | £82 | £84 | £83 |
| 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 £45 per night before taxes and fees

Verified guest reviews
Over 800 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

4.8 Average rating
Massa Marittima stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Family-friendly rentals Grosseto
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- Family-friendly rentals Italy
- Elba
- Giglio Island
- Cala Violina
- Feniglia
- Del Chianti
- Spiaggia Di Sansone
- Spiagge Bianche
- Spiaggia Di Barbarossa
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Le Cannelle
- Spiaggia di Marina di Campo
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Palazzo Pubblico
- CavallinoMatto
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Terme San Filippo
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Mount Amiata





