
Holiday houses in Massa Marittima
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Top-rated holiday 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.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

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.

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

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

Luxurious Medieval Tower & Private Concierge
It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

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!
Popular amenities for Massa Marittima holiday rentals
Other great holiday rentals in Massa Marittima

Luxury Medieval Tower - Penthouse

Open Space Piscina e Giardino

Flat with a view of Massa Marittima Cathedral

Il Bell'Arco

Penthouse with a view for 8 people

Poggiolo

Elegant farmhouse overlooking Pienza

Panoramic villa garden bike
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $149 AUD | $150 AUD | $148 AUD | $136 AUD | $139 AUD | $142 AUD | $149 AUD | $163 AUD | $155 AUD | $148 AUD | $148 AUD | $149 AUD |
| 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 |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Massa Marittima?
Yes! Work meets play with ease at over 30 vacation rentals in Massa Marittima featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Massa Marittima vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Massa Marittima, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Massa Marittima?
Experience the best of Massa Marittima with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Massa Marittima?
Four-legged friends are welcome in Massa Marittima. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Massa Marittima?
Massa Marittima has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Massa Marittima have air conditioning?
Absolutely! We offer over 10 condo rentals with air conditioning in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Massa Marittima have a kitchen?
Absolutely! We offer over 50 apartment rentals with a kitchen in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Massa Marittima have wifi?
Absolutely! We offer over 50 apartment rentals with wifi in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Massa Marittima have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Massa Marittima?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 50 homes with wifi, over 20 homes with free parking, over 50 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Massa Marittima

Total holiday rentals
Explore 100 holiday rentals in Massa Marittima

Nightly prices starting at
Massa Marittima holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 1,950 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Massa Marittima holiday rentals include Wi-Fi 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
- House rentals Massa Marittima
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- 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





