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

Case nell'aia Arco, apartment in Chianti and pool
L'appartamento Arco si trova in un tipico borgo toscano tra vigneti e oliveti. Appartamento arredato in stile rustico toscano, accogliente per farvi rilassare e visitare la zona. L'appartamento si affaccia sulla grande terrazza dove potete fare pranzi e cene all'aperto o aperitivi. Cucina, divano e punto TV, wifi, due camere matrimoniali, bagno, terrazza, piscina. Parcheggio auto nella proprietà . Ideale come punto di partenza per visitare Siena, Firenze, San Gimignano, sia in auto che in bici.

Tuscan Villa for Family & Friends in Montepulciano
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

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.

House at Gianni - Olmo
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!

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

"L'Assolata" Cottage in Tuscany
A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

sea view villa with private infinity pool
RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Panoramic penthouse in the ancient village
Penthouse with two panoramic terraces with stunning views of the valley and the historic center, in the square below the historic Orsini Fortress. Twenty minutes from the Terme di Saturnia and five minutes from the Terme di Sorano, immersed in the Maremma landscape.

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.

Antico Borgo Ripostena – n. 8 Old House
Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning.
Popular amenities for Massa Marittima family-friendly rentals
Family-friendly home rentals with a hot tub

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Il Fienile, Cottage in the country with Jacuzzi

Amazing Tuscany Villa, FREE parking

"Sunflower" apartment with view of Siena

La Villa farm stay - L'Olivo, Pool & Hot Tub

Villa in Montepulciano with a Pool
Wp Relais Villa Vignalunga

VILLA Amazing pool , tennis , 7km Florence,
Family- and pet-friendly home rentals

Authentic Tuscan Country House WITH A/C

Costalmandorlo, a rustic home in the heart of Tuscany

Casa Bonari - a paradise for the eyes

Poggio Bicchieri Holiday Farm - Memoria apartment

Your Tuscan oak tree house, enchanting Val d'Orcia

Suite in Castello di Valle
La Piazzetta - Cozy open space in the historic center of Montepulciano

Pieve di Caminino Historic Farm
Family-friendly home rentals with a pool

Panoramic Country Suite Montalcino

Penthouse with pool view a few km from Follonica

Cercis - La Palmierina

Stone House with Exclusive Pool Codilungo in Chianti

Podere La Castellina - No. 3 JUNIPER

Bel Casale with sea view and the mediaeval village

Villa Isabella

Podere Cavone Villa Vigna A breathtaking view
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £67 | £63 | £76 | £78 | £79 | £81 | £82 | £108 | £87 | £81 | £84 | £82 |
| 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 £44 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
- Marina di Cecina
- Del Chianti
- Cala Violina
- Feniglia
- Cascate del Mulino
- Spiaggia Di Sansone
- Gulf of Baratti
- Spiagge Bianche
- Spiaggia di Capo Bianco
- Spiaggia Di Barbarossa
- Spiaggia di Marina di Campo
- Le Cannelle
- Spiaggia della Padulella
- Palazzo Pubblico
- Arcipelago Toscano National Park
- CavallinoMatto
- Santa Maria della Scala
- Ugolino Golf Club
- Antinori nel Chianti Classico
- Parco Regionale Della Maremma
- Siena Cathedral
- Abbey of Monte Oliveto Maggiore




