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Holiday rentals in Massa Marittima

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Top-rated holiday rentals in Massa Marittima

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Top guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Apartment
5 out of 5 average rating, 173 reviews

Ancient 17th century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. The apartment is furnished in the perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and thoughtful furnishings and products from local artisans that will help you have a pleasant stay . In the large outdoor courtyard you'll find a salt pool on a panoramic terrace with wonderful views of castle hills and vineyards with breathtaking sunsets.

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home
4.96 out of 5 average rating, 105 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 favourite
Flat
4.91 out of 5 average rating, 183 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 favourite
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
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!

Guest favourite
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.
Holiday home
4.93 out of 5 average rating, 107 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 favourite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay
4.99 out of 5 average rating, 263 reviews

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.

Top guest favourite
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.
Apartment
4.99 out of 5 average rating, 176 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 favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Apartment
4.97 out of 5 average rating, 319 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and Wi-Fi A strategic location for visiting Tuscany and Umbria.

Top guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Flat
4.97 out of 5 average rating, 116 reviews

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.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 436 reviews

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.

Top guest favourite
A ceramic vase filled with vibrant yellow flowers is prominently displayed on a table. Soft light from a lamp illuminates the rustic stone wall in the background, enhancing the warm ambiance of the space. Two mugs sit beside the vase, adding a touch of comfort.
Flat
4.92 out of 5 average rating, 105 reviews

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.

Top guest favourite
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
4.91 out of 5 average rating, 236 reviews

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!

Popular amenities for Massa Marittima holiday rentals

When is the best time to visit Massa Marittima?

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Avg. price£60£67£64£73£74£76£79£87£82£65£66£66
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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 apartment rentals in Massa Marittima?

    Experience the best of Massa Marittima with our apartment rentals, starting at about $30 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 20 homes with air conditioning, over 60 homes with a kitchen, over 50 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

  • 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 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 £23 per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of Massa Marittima holiday rentals include wifi 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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