
Villa vacation rentals in Massa Marittima
Find and book unique villas on Airbnb
Top-rated villa rentals in Massa Marittima
Guests agree: these villas are highly rated for location, cleanliness, and more.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
FamilyValueShared spaces

Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
ValueFamilyAccuracy

Villa dei 2 Ulivi (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
FamilyLocationAccuracy

Torre dei Belforti
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.
FamilyLocationNearby

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
Cozy Chianti getaway near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!
LocationValueAir conditioning

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
LocationValueAccuracy

Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.
FamilyValueLayout

Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant
ValueLocationQuiet

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.
FamilyLocationKitchen

Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
ValueLocationHeating

La Dimora Dei Conti: Indulge in a Country Farmhous
Only a Four minute drive away or 20 mins walk from the city and the Lucca train station stands La Dimora Dei Conti a superb luxury apartment located in a farmhouse villa that dates back to the 15th century and now completely and painstakingly renovated to transport you to the an era of modern beauty and traditional Tuscan feeling.<br><br>As soon as you enter the foyer you will feel the special atmosphere that permeates the villa.
ValueFamilyHot tub

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).
FamilyLocationHeating
Popular amenities for Massa Marittima villa rentals
Private villa rentals

Agriturismo Podere Scaluccia Chianti, Florence
FamilyLocationView

Tuscany Country House Villa Claudia
LocationFamilyBreakfast

Villa Il Diaccio with view of the Tuscan Maremma
ValueFamilyAmenities

Villa Holm stunning view 10 mn walk to city centre
FamilyLocationCleanliness

Luxury Villa with swimming pool ModdissiCharme IsolaElba
LocationFamilyHospitality

The Villa of the Spendthrift Brigade!
LocationFamilyOutdoor spaces

Capanna di Elfo - Capanna Di Elfo
LocationValueNearby

Villa Castiglioncello - access to the private sea
LocationFamilyOutdoor spaces
Luxury villa rentals

Villa Gourmet Food, Pizza, Chef, Pool and Nature
LocationFamilyLayout

VILLA GIOMA - Completely renovated country house
LocationFamilyCheckout

Exclusive villa Lionella with private pool
ValueLocationView

Tuscany Villa With Pool & Magnificent Garden
FamilyValueSleep quality

Mulino Morandi - Mulino Morandi
LocationIndoor spacesWifi

Luxury Villa + Annex with Jacuzzi + Pool, Chef
FamilyLocationSleep quality

Romantic Villa with private pool - "Il Pollaio"
LocationFamilyCheckout

Tuscan Villa with Pool & Jacuzzi, San Gimignano
LocationValueWalkability
Villa rentals with a pool

Villa La Doccia, Greve in Chianti
LocationFamilyWifi

Villa Isabella
LocationFamilyAccuracy

Gli sterpi
FamilyLocationOutdoor spaces

Casa Colombaia, in the Chiantishire
LocationFamilyIndoor spaces

Villa Le Rocche with pool, breathtaking view
ValueFamilySleep quality

Exclusive villa with pool jacuzzi wifi and green
LocationFamilyPool

Casa di Leo Romantic House
FamilyLocationGrill

Lucignano Secondo – La Villa
LocationFamilyCheck-in
Destinations to explore
- Rentals with pools Massa Marittima
- Family-friendly rentals Massa Marittima
- Pet-friendly rentals Massa Marittima
- Rentals with breakfast Massa Marittima
- Chalet rentals Massa Marittima
- Condo rentals Massa Marittima
- Apartment rentals Massa Marittima
- House rentals Massa Marittima
- Villa rentals Grosseto
- Villa rentals Tuscany
- Villa rentals Italy
- Elba
- Giglio Island
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Del Chianti
- Le Cannelle
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Mount Amiata
- Antinori nel Chianti Classico
- CavallinoMatto
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Quercetano
- Valdichiana Outlet Village
- Casa Barthel
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Spiaggia di Fetovaia
- Abbey of Sant'Antimo





