
Family-friendly vacation 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.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with all the families in this home. The farmhouse consists of two independent apartments with a living room, kitchen, bedroom and bathroom. You will not have to share anything with the other guests as we have taken care to organize everything so that everyone has their own spaces and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. Nearby Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Old Farmhouse near Panzano Castle Abbacìo
The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

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.

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.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

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.

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.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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!

Michelangelo: entire space in the heart of Tuscany
Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.
Popular amenities for Massa Marittima family-friendly rentals
Family-friendly home rentals with a hot tub

"Red Rose" apartment with view of Siena.

Il Fienile, Cottage in the country with Jacuzzi

Amazing Tuscany Villa, FREE parking

Beautiful renovated barn in Tuscany

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

Your Private Tuscan Retreat

Villa di Geggiano – Guesthouse

Poggio dell'orso.Traditional Casale. Amazing views
Family- and pet-friendly home rentals

the sunset loft

Appartment 1 surrounded by Tuscan Nature

Authentic Tuscan Country House WITH A/C

Stuart White Tea Central Panoramic & Garden

Holiday in antique farm, Belvedere

Casa del Poggio, with a beautiful sea view

Countryside Cottage With View - Le Rondini apt

Secret Garden Siena
Family-friendly home rentals with a pool

Cercis - La Palmierina

San Giovanni in Poggio, villa Meriggio 95mq

Podere La Castellina - No. 1 COTTAGE

Podere Guidi

FIENILE VILLACOLLE Tuscan hill

Tuscan countryside, peace and relaxation 10 minutes from Siena

Visit Chianti,Siena, Florence, S.Gimignano

Villa Gourmet Food, Pizza, Chef, Pool and Nature
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $127 CAD | $119 CAD | $143 CAD | $148 CAD | $150 CAD | $153 CAD | $144 CAD | $146 CAD | $139 CAD | $144 CAD | $140 CAD | $127 CAD |
| 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 vacation rentals that are family-friendly in Massa Marittima

Total vacation rentals
Explore 40 vacation rentals in Massa Marittima

Nightly prices starting at
Massa Marittima vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 760 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Massa Marittima vacation 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
- Provence Vacation rentals
- Rome Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Marseille Vacation rentals
- Cannes Vacation rentals
- Italian Riviera Vacation rentals
- Bologna Vacation rentals
- Pet-friendly rentals Massa Marittima
- Rentals with breakfast Massa Marittima
- Villa rentals Massa Marittima
- House rentals Massa Marittima
- Rentals with outdoor seating Massa Marittima
- Rentals with a washer and dryer Massa Marittima
- Rentals with a patio Massa Marittima
- Chalet rentals Massa Marittima
- Rentals with a fireplace Massa Marittima
- Condo rentals Massa Marittima
- Smoking-friendly rentals Massa Marittima
- Apartment rentals Massa Marittima
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Elba
- Giglio Island
- Feniglia
- Cala Violina
- Gulf of Baratti
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Kite Beach Fiumara
- Spiaggia Libera
- Spiagge bianche
- Spiaggia Di Barbarossa
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia della Padulella
- Spiaggia Marina di Cecina
- Spiaggia Zuccale
- Cala Di Forno
- Spiaggia di Patresi
- Castiglion del Bosco Winery
- Marina di Grosseto beach
- Spiaggia di Marina Di Campo
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Cavo
- Le Cannelle