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Holiday home rentals in Grosseto

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Grosseto

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Top guest favourite
Holiday home in San Giovanni D'Asso
4.94 out of 5 average rating, 109 reviews

Elegant house with pool, Valdorcia Deluxe 1

In the Val D'Orcia DELUXE apartments, you can relax in the midst of nature in a spacious and very welcoming home. The house is equipped with everything you need (including dishwasher, washing machine, microwave, wifi, Playstation) and has large outdoor spaces with a swimming pool, gazebos, LCD TV, tables, sofas. You will be followed by booking until your arrival with all the useful information and of course we will always be at your disposal throughout the stay. I look forward to seeing you soon!

Guest favourite
Holiday home in Montepulciano
4.92 out of 5 average rating, 189 reviews

Stuart Jasmine central, panoramic top location

This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Top guest favourite
Holiday home in Monticchiello
5 out of 5 average rating, 23 reviews

Elegant farmhouse overlooking Pienza

Podere Fonte Bernardi is an authentic Tuscan country house. Surrounded by the nature of the Val d'Orcia, an ideal place to relax. Located a few km from the most beautiful places in Tuscany such as Pienza, the medieval village of Monticchiello, the thermal site of Bagno Vignoni and the homeland of Montepulciano wine. Perfect for taking long walks and discovering local wines and food. You will be able to enjoy the most beautiful sunset over Pienza in the silence of the most authentic nature.

Guest favourite
Holiday home in Massa Marittima
4.93 out of 5 average rating, 103 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
Holiday home in Roccastrada
5 out of 5 average rating, 23 reviews

Apartment in a wine estate in Tuscany

Welcome to our 18th century villa in Sticciano, nestled between Florence and Rome, in the Tuscan Maremma! The beautiful villa has been trasformed into a wine estate hostelry, offering ten apartments for an unforgettable stay. Expect to see rolling hills, vineyards, and expansive green landscapes. A traditional Tuscan dinner is served twice a week, and our delicious breakfast is available every morning on request. Enjoy the pool or a wine experience visiting our vineyards and cellars!

Guest favourite
Holiday home in Montemerano
4.92 out of 5 average rating, 37 reviews

Casa Monteme, modern loft with views of the Maremma

Casa Montemè is located in the hills of Maremma, just a short walk from the Terme di Saturnia, in the ancient medieval village of Montemerano. Natural materials, traditional techniques, local craftsmanship and some contemporary touches have transformed an old traditional house into the vacation home of your dreams. Its location makes it ideal for those looking for a little relaxation and want to enjoy the wonderful villages of Tuscany! Kick back and relax in this calm, stylish space.

Top guest favourite
Holiday home in Sorano
4.9 out of 5 average rating, 30 reviews

Palazzo Palloni: Main Floor

"Piano Nobile," nestled in the heart of the medieval town of Sorano, boasts 150 square meters of elegant living space, blending modern design with historic charm. As you step in, you'll find a spacious living room that flows into an open-plan kitchen, perfect for gathering with friends and family. With three bedrooms and two baths, it comfortably accommodates six guests. High-quality materials and designer lighting, all adds up to an unforgettable experience in the heart of Tuscany.

Superhost
Holiday home in Campagnatico
4.84 out of 5 average rating, 19 reviews

Cozy Cottage with a beautiful view - Casa Luciano

Casa Luciano is perfect for a couple or a small family with one child. It is the ideal place for anybody wishing to get away from it all and to relax and experience real Tuscan life without having to use the car every day. The huge pool, beautiful garden and great views make it a perfect stay for everyone. 'Podere Fulignano' with its four houses is a beautiful old farm house complex which has been lovingly restored. It is situated in the middle of a 300 year old olive grove.

Superhost
Holiday home in Monte Cucco
4.84 out of 5 average rating, 44 reviews

Prachtig huisje in Tuscany, Luca's House

Enjoy this stylish place, part of three cultivated farms on the edge of the Montecucco wine region. A beautiful sweeping view of the hills all around. Imagine having a glass of Brunello or Montecucco, Italian snacks on hand, watching the setting sun. Take a refreshing dip in the pool, feel the warmth of the sun, and immerse yourself in Italian life. Make the most beautiful day trips to the Val D'Orcia, Bagno Vignoni, Siena, Florence, Montalcino, Montepulciano and the sea.

Guest favourite
Holiday home in Scarlino
5 out of 5 average rating, 14 reviews

Glamping Green Sensations "Suite Diamond"

Benvenuti nella "Suite Diamond" del nostro Glamping 'Green Sensations'. Questo trilocale di 50mq offre comfort lussuosi, due bagni privati e due camere matrimoniali accoglienti, con un divano letto comodamente usufruibile da una persona. Potrete rilassarvi nella vasca idromassaggio esterna e godere della bellezza naturale che ci circonda, con vista sulla natura Toscana. Questa suite è dotata di tavolo in giardino con lettini prendisole, ombrellone e tavolo da Ping-Pong.

Guest favourite
Holiday home in Porto Ercole
4.97 out of 5 average rating, 62 reviews

House on the harbor - Il Partito

In the heart of Porto Ercole, on the seafront, this charming vacation home of about 70 square meters is for rent, located on the first floor. Its balcony overlooking the harbor offers a striking view of the sea and moored boats, immersing you in the magical atmosphere of Argentario. Thanks to its privileged location, bars, restaurants and shops are a short walk away. As the owner of the IDROBOAT dinghy rental, I will be happy to suggest the most beautiful beaches.

Superhost
Holiday home in Porto santo Stefano
4.84 out of 5 average rating, 38 reviews

Sunny Seaside Cottage

In Monte Argentario, in the stretch of coast that connects Porto Santo Stefano to Porto Ercole , overlooking the sea and with a breathtaking view of the islands of Giglio and Giannutri , there is this charming two-room independent apartment,completely isolated from the view of other houses and the street It consists of double bedroom, living room with spacious stove top and sofa bed , bathroom with shower. In the garden area equipped with grill , oven

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