
Holiday houses in Massa Marittima
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Quick stats about holiday rentals in Massa Marittima

Total holiday rentals
Explore 110 holiday rentals in Massa Marittima

Nightly prices starting at
Massa Marittima holiday rentals start at $69 NZD per night before taxes and fees

Verified guest reviews
Over 1,980 verified reviews to help you choose

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

Pet-friendly accommodation
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 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!
Top-rated holiday rentals in Massa Marittima
Guests agree: these stays are highly rated for location, cleanliness and more.

Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Private House for 4P – La Capanna Di Azzurra
Ideal for families, couples or friends looking for an elegant and welcoming home, this house is designed for those who want to experience the Tuscan countryside without sacrificing the comfort of the city. Imagine a breakfast looking at the profile of Siena, days between art, wine and nature, and the return at sunset, when the light warms the stone and the silence restores the authentic rhythm of these places. A practical, charming and scenic retreat, perfect for visiting Siena and its surroundings!

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.

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!

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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.

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

Sunsets wow-relax and slow vacation
casa PàMa is a retreat where every detail has been carefully considered to make you feel at the heart of a unique experience. The day begins with a slow breakfast on the balcony, with birdsong in the background and a view of the Tuscan hills stretching all the way to the sea. In the evening, enjoy unforgettable sunsets while sipping a glass of wine. Here, you can finally slow down, savor every moment in complete harmony. Drive right up to the house without worrying about your luggage.

Design loft with private SPA in Tuscany
Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

apartment in the medieval heart of Massa Marittima
The accommodation in the medieval heart offers great peace, in one of the main pedestrian streets that leads to the Candeliere gate on one side, and Piazza Garibaldi and San Cerbone Cathedral, a stone's throw away. The accommodation was completely redone and equipped in 2024. It consists of two bedrooms, one of which can be used as a living room, and a large kitchen/dining room. Two terraces with character, enhance the accommodation, for your breakfasts/apéritifs/reading.

AnticaVista, Luxury Apartment with Tower Views
A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”
Popular amenities for Massa Marittima holiday rentals
Other great holiday rentals in Massa Marittima

Luxury Medieval Tower - Penthouse

TerraMadre ANIMA

Il Bell'Arco

Luxury Medieval Tower • Exclusive Chianti Stay

Experience Real Tuscany from our Country Home

Infinity Pool in the green agritourism with a view of the woods

The House in the Castle and the Terrace overlooking the Village

Herons Superior Apartment - Splendid 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 | $181 NZD | $183 NZD | $179 NZD | $166 NZD | $169 NZD | $172 NZD | $181 NZD | $198 NZD | $188 NZD | $179 NZD | $179 NZD | $181 NZD |
| 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 50 vacation rentals in Massa Marittima featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in bed and breakfast rentals in Massa Marittima?
Experience the best of Massa Marittima with our bed and breakfast rentals, starting at about $100 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 70 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 bed and breakfast rentals in Massa Marittima have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Massa Marittima have a kitchen?
Absolutely! We offer over 10 condo 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.
Destinations to explore
- Rentals with pools Massa Marittima
- Family-friendly rentals Massa Marittima
- Pet-friendly rentals Massa Marittima
- Rentals with outdoor seating Massa Marittima
- Villa rentals Massa Marittima
- Rentals with breakfast Massa Marittima
- Chalet rentals Massa Marittima
- Rentals with a fireplace Massa Marittima
- Condo rentals Massa Marittima
- Apartment rentals Massa Marittima
- Smoking-friendly rentals Massa Marittima
- Rentals with a patio Massa Marittima
- Rentals with a washing machine and dryer Massa Marittima
- House rentals Massa Marittima
- Elba
- Giglio Island
- Cala Violina
- Feniglia
- Parco Regionale Della Maremma
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Del Chianti
- Le Cannelle
- Spiaggia Di Barbarossa
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Cascate del Mulino
- Mount Amiata
- CavallinoMatto
- Antinori nel Chianti Classico
- Siena Cathedral
- Palazzo Pubblico
- Ugolino Golf Club
- Val di Chiana
- Valdichiana Outlet Village
- Terme San Filippo
- Quercetano





