
Vacation rentals in Massa Marittima
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Top-rated vacation rentals in Massa Marittima
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Sunsets wow-Arriving by car at home
Casa PàMa has an exclusive little balcony with a view, is a 1-minute walk from the historic centre of Massa Marittima, a medieval town between the hills and the sea, is conveniently accessible by car to check in (parking spaces nearby). It is the ideal starting point for visiting the Tuscan Maremma - unspoilt beaches - villages such as San Gimignano, Volterra, Pitigliano - experiences for every season: wine tasting, trekking, thermal baths, MTB routes, sea, excursions to Elba Island, Giglio

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.

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

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.

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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Leo's porch
Stay in this unique place and spend unforgettable evenings gazing at the horizon. Breathe clean air and enjoy the relaxation offered by the village of Scarlino. Ideal for couples or small families who want functional and comfortable accommodation. FROM MAY 1 TO AUGUST 31, a tourist tax of €1.00 per night/person is applied for each day of stay. Bed linen and towels are NOT INCLUDED in the final price of the accommodation.

Casa al Gianni - Hut
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!

Suite in Castello di Valle
A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.
Popular amenities for Massa Marittima vacation rentals
Other great vacation rentals in Massa Marittima

Luxury Medieval Tower - Penthouse

Via Goldoni 16

Trebbiano apt: overlooking olive grove & vineyard

Apartment in a wine estate

Il Bell'Arco

Capezzuolo 33

Antea Terra - House by the sea with hot tub

To be happy in Tuscany with comfort & view!
When is the best time to visit Massa Marittima?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$16,518 GYD | G$18,609 GYD | G$17,773 GYD | G$20,073 GYD | G$20,491 GYD | G$20,909 GYD | G$21,955 GYD | G$24,045 GYD | G$22,791 GYD | G$21,745 GYD | G$21,745 GYD | G$21,955 GYD |
| 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 40 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 50 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 apartment rentals in Massa Marittima have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning 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 60 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
Do apartment rentals in Massa Marittima have a kitchen?
Absolutely! We offer over 60 apartment rentals with a kitchen in Massa Marittima. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Massa Marittima

Total vacation rentals
Explore 110 vacation rentals in Massa Marittima

Nightly prices starting at
Massa Marittima vacation rentals start at G$6,273 GYD per night before taxes and fees

Verified guest reviews
Over 1,930 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 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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- Elba
- Giglio Island
- Marina di Cecina
- Del Chianti
- Spiagge Bianche
- Cala Violina
- Feniglia
- Cascate del Mulino
- Spiaggia Di Sansone
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Siena Cathedral
- Spiaggia di Marina di Campo
- Le Cannelle
- CavallinoMatto
- Palazzo Pubblico
- Santa Maria della Scala
- Arcipelago Toscano National Park
- Antinori nel Chianti Classico
- Spiaggia Di Sottobomba
- Ugolino Golf Club
- Casa Barthel




