
Villa holiday rentals in Massa Marittima
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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
LocationValueOutdoor spaces
4.93 out of 5 average rating, 256 reviews
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.
FamilyValueLayout
4.95 out of 5 average rating, 146 reviews
Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
LocationFamilySleep quality
4.98 out of 5 average rating, 127 reviews
Belforti Tower
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.
LocationFamilyDecor
4.99 out of 5 average rating, 138 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
LocationFamilyGetting around
4.96 out of 5 average rating, 102 reviews
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.
LocationFamilyPool
4.98 out of 5 average rating, 107 reviews
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.
ValueLocationWifi
4.98 out of 5 average rating, 120 reviews
Beautiful Country House, near Siena with jacuzzi
Beautiful and ancient country house, located just 10 km from Siena (15 minutes by car from the city center). The house can accommodate up to 8 people. Surrounded by greenery, in a panoramic position with a beautiful garden where there is a hot tub, available, on request, even in winter. The very large property is fully fenced and offers maximum privacy. Please note: the hosts are also the owners and managers of the "Borgo dei Fondi" holiday home in Siena.
LocationFamilyHospitality
4.96 out of 5 average rating, 104 reviews
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.
ValueFamilyWalkability
5.0 out of 5 average rating, 190 reviews
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.
LocationValueWifi
4.89 out of 5 average rating, 309 reviews
Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
LocationFamilySleep quality
4.96 out of 5 average rating, 209 reviews
"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).
FamilyLocationCondition
4.95 out of 5 average rating, 174 reviewsPopular amenities for villa rentals in Massa Marittima
Private villa rentals

Villa unesco heritage, Jacuzzi & garden. BB Daria
ValueFamilyCheck-in
4.98 out of 5 average rating, 183 reviews
La Dimora Dei Conti: Indulge in a Country Farmhouse
LocationValueBack garden
4.93 out of 5 average rating, 217 reviews
Villa L'Olivo w/Private pool (Close San Gimignano)
LocationValueHeating
4.99 out of 5 average rating, 101 reviews
Casa Pineta Elba, a short walk from the sea
FamilyLocationGetting around
5.0 out of 5 average rating, 43 reviews
Podere la Pompa
FamilyLocationAmenities
5.0 out of 5 average rating, 27 reviews
L'Apparita del Peruzzi | Villa | Private Pool & A/C
LocationFamilyNearby
5.0 out of 5 average rating, 22 reviews
Villa Casale "Il Diaccio" with views of the Maremma
LocationFamilyQuiet
4.94 out of 5 average rating, 18 reviews
Badia a Passignano Guard
LocationComfortView
4.86 out of 5 average rating, 7 reviewsLuxury villa rentals

Poggio del Fattore-Villa with pool, hilltop, Chianti
FamilyValueNearby
4.99 out of 5 average rating, 131 reviews
Villa of the 2 Olive Trees (Abbadia Isola)
FamilyLocationAccuracy
4.97 out of 5 average rating, 174 reviews
Podere Scaluccia Chianti Agritourism, Florence
FamilyValueNearby
4.99 out of 5 average rating, 123 reviews
Farmhouse , pool, 13 px. Lucca 10km
FamilyLocationComfort
4.99 out of 5 average rating, 148 reviews
Charming Villa in Stone in Tuscany, Borgo ai Lecci
LocationFamilyBreakfast
4.97 out of 5 average rating, 116 reviews
La Guardiola, Capo Perla
LocationFamilyHospitality
5.0 out of 5 average rating, 36 reviews
Romantic Villa with private pool - "Il Pollaio"
FamilyLocationCheckout
5.0 out of 5 average rating, 48 reviews
Villa Holm stunning view 10 mn walk to city centre
LocationFamilyCondition
5.0 out of 5 average rating, 56 reviewsVilla rentals with a pool

Farmhouse in Chianti
LocationFamilyAccess
4.95 out of 5 average rating, 221 reviews
HistoricVilla-6km from Luccacentre-Villa Zambaldi
ValueFamilyBathroom
4.93 out of 5 average rating, 116 reviews
romignano wine farm
ValueFamilyCondition
4.72 out of 5 average rating, 58 reviews
Stone villa with pool
FamilyLocationAccuracy
5.0 out of 5 average rating, 23 reviews
Exclusive villa with pool jacuzzi wifi and green
FamilyValueHospitality
4.96 out of 5 average rating, 54 reviews
Villa in Tuscany with private panoramic pool
LocationFamilyComfort
5.0 out of 5 average rating, 35 reviews
Casale i Cipressi
LocationFamilyAir conditioning
5.0 out of 5 average rating, 27 reviews
Private Villa with Swimming Pool and Hot Tub
FamilyLocationCondition
4.94 out of 5 average rating, 35 reviewsDestinations to explore
- Pet-friendly rentals Massa Marittima
- Rentals with pools Massa Marittima
- Family-friendly rentals Massa Marittima
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- Villa rentals Grosseto
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- Villa rentals Italy
- Elba
- Giglio Island
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Del Chianti
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Mount Amiata
- Cascate del Mulino
- Antinori nel Chianti Classico
- Siena Cathedral
- CavallinoMatto
- Val di Chiana
- Quercetano
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona





