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Vacation rentals in Massa Marittima

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Massa Marittima

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia
4.92 out of 5 average rating, 566 reviews

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!

Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 317 reviews

Podere Vergianoni immerso nelChianti con piscina

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.

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 122 reviews

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.

Top guest favorite
Apartment in Caminino
4.91 out of 5 average rating, 188 reviews

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.

Guest favorite
A bright living area is seen, featuring a cozy sofa and a media unit with woven baskets. Steps lead to a charming stone wall, enhancing the space's historic character. Soft lighting creates a subtle ambiance, contributing to the warm atmosphere of the loft.
Loft in Massa Marittima
4.87 out of 5 average rating, 201 reviews

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!

Top guest favorite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 226 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favorite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 101 reviews

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.

Guest favorite
The living and dining area features exposed stone walls and wooden beams, enhancing the rustic charm. A spacious sofa sits adjacent to a wooden dining table, surrounded by four chairs. Natural light filters in through a window, illuminating the tiled flooring.
Vacation home in Massa Marittima
4.94 out of 5 average rating, 108 reviews

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

Top guest favorite
The bedroom features a spacious bed with an elegant wrought-iron headboard, flanked by bedside lamps. A decorative chandelier hangs from the wooden ceiling beams. A colorful painting and a framed mirror adorn the walls, while a vase with flowers adds a touch of charm.
Condo in Pitigliano
4.99 out of 5 average rating, 111 reviews

The Ancient Views in Pitigliano

Spacious and elegant apartment (130 sq m), beautifully furnished with a nod to tradition. Generous living areas provide the perfect setting to unwind, recharge, or enjoy quality time with friends. Ideal for a couple, two pairs of friends, or a family of four. Bedrooms are equipped with air conditioning. However, if you're passionate about combating climate change, you can opt for the ceiling and floor fans available in every room. They ensure a refreshing stay, even on the warmest days.

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 207 reviews

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.

Top guest favorite
A modern kitchen area features grey cabinetry, a built-in oven, and ample counter space. A white dining table is accompanied by four chairs with striped patterns. A large arched window allows natural light to illuminate the space, while potted plants add a touch of greenery.
Condo in Massa Marittima
4.99 out of 5 average rating, 177 reviews

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.

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.92 out of 5 average rating, 255 reviews

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 vacation rentals

When is the best time to visit Massa Marittima?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,526 GYDG$18,617 GYDG$17,781 GYDG$20,082 GYDG$20,500 GYDG$20,918 GYDG$21,964 GYDG$24,056 GYDG$22,801 GYDG$21,755 GYDG$21,755 GYDG$21,964 GYD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°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 condo rentals in Massa Marittima have wifi?

    Absolutely! We offer over 10 condo 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 20 homes with free parking, over 50 homes with wifi, 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 vacation rentals in Massa Marittima

  • Total vacation rentals

    Explore 100 vacation rentals in Massa Marittima

  • Nightly prices starting at

    Massa Marittima vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,950 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation 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 vacation 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!

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