
House vacation rentals in Massa Marittima
Find and book unique houses on Airbnb
Quick stats about house rentals in Massa Marittima

Nightly prices starting at
Massa Marittima vacation rentals start at G$18,824 GYD per night before taxes and fees

Verified guest reviews
Over 130 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Massa Marittima rentals

4.9 Average rating
Massa Marittima stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Massa Marittima
Guests agree: these houses are highly rated for location, cleanliness, and more.

Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available
LocationFamilyLong stay

Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
ValueFamilyWifi

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
ValueLocationAccuracy

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.
LocationFamilyQuiet

TREEhouse / casaBARTHEL
casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.
LocationValueKitchen

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.
ValueLocationHiking

Open space surrounded by nature
Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring
FamilyValueHeating

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.
LocationValueLaundry

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.
LocationFamilyHot tub

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of Chianti Classico, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with a breathtaking view, where you can enjoy stunning sunsets. The total independence of the house, the cozy garden, and the large loggia allow you to spend your stay in total peace of mind. Our reviews are your best guarantee.
LocationFamilySleep quality

The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
FamilyLocationCondition

"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.
LocationValueOutdoor spaces
Popular amenities for Massa Marittima house rentals
House rentals with a pool

Podere Scorno country house with swimming pool
LocationLong stayWalkability

Infinity pool in Chianti 1
FamilyLocationComfort

Cercis - La Palmierina
FamilyLocationQuiet

Private villa/swimming pool in Tuscany
LocationFamilyAccess

SuiteLouise.pool, Hot Tub,homeGym & private Garden
FamilyLocationView

Explore Chianti from a Charming Stone House
ValueFamilyHospitality

Casa Giulia di Sopra Farmhouse
FamilyLocationGetting around

Borgo Ripostena – No. 8 Casa Vecchia
LocationValueComfort
Weekly house rentals

Love in Chianti
LocationValueBathroom

Design loft with private SPA in Tuscany
LocationValueComfort

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
LocationFamilyLong stay

Siena Countryside Colle Ciupi
LocationValueDecor

The charming cottage in Tuscany with breathtaking views
LocationValueComfort

Raffaella's House in Chianti
ValueFamilyLayout

Authentic Tuscany Experience in our Country House
ValueLocationSleep quality

Nada Home
FamilyValueNearby
Private house rentals

The Laurel
FamilyLocationBeach

Villa Tuscany 5 bedrooms panoramic terrace
FamilyValueGetting around

La Mignola Apartment
FamilyLocationLong stay

Beautiful farmhouse in the Chianti panoramic garden
LocationFamilyCondition

Casa San Ripa: Relax Oasis with Private Pool
FamilyLocationWifi

Villa of the Hydrangeas
FamilyLocationAccuracy

The Maison at the Ponte Vecchio
LocationFamilyDecor

The little house in the banditelle
LocationKitchenGetting around
Destinations to explore
- Rentals with pools Massa Marittima
- Family-friendly rentals Massa Marittima
- Pet-friendly rentals Massa Marittima
- Villa rentals Massa Marittima
- Rentals with breakfast Massa Marittima
- Chalet rentals Massa Marittima
- Condo rentals Massa Marittima
- Apartment rentals Massa Marittima
- House rentals Grosseto
- House rentals Tuscany
- House rentals Italy
- Elba
- Giglio Island
- Parco Regionale Della Maremma
- Cala Violina
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Del Chianti
- Spiaggia Di Sansone
- Le Cannelle
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Cascate del Mulino
- Spiaggia Di Barbarossa
- Mount Amiata
- CavallinoMatto
- Antinori nel Chianti Classico
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Quercetano
- Terme San Filippo
- Valdichiana Outlet Village
- Ugolino Golf Club





