Vacation home rentals in Grosseto

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Top-rated vacation home rentals in Grosseto

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Superhost

A tranquil pool area is highlighted with sun loungers and thatched umbrellas. In the background, a two-story building is framed by lush greenery and blooming flowers, creating a serene outdoor escape.

Vacation home in Scarlino

4.63 out of 5 average rating, 24 reviews

charming house with pool - Res. "La Beccanina"

Delightful apartment in tourist complex "LA BECCANINA"-SCARLINO. Immersed in the beautiful Tuscan Maremma a few kilometers from the beach of Cala Violina, Cala Martina and the most renowned towns in the area. It offers a swimming pool, dining areas, barbecue and private parking. First floor, it consists of 2 double bedrooms (1 double + 1 (2 single beds), 2 bathrooms with shower, living room with fireplace, living room with kitchen and large terrace overlooking the pool. Air conditioning in all rooms

Guest favorite

The exterior of the stone house is featured, showcasing rustic charm with green shutters and a welcoming entrance. The garden area includes tables and chairs, surrounded by lush greenery and potted plants, offering a serene outdoor space for relaxation.

Vacation home in Montisi

4.94 out of 5 average rating, 18 reviews

Unique & Historic Getaway: Dreamy Garden

Questo elegante alloggio è perfetto per viaggi di gruppo o familiari, all'interno di un piccolo, ma prezioso borgo toscano, Montisi, nel Comune di Montalcino, famoso per il vino e per essere nel parco della Val d'Orcia, sito UNESCO. La casa ha un giardino pensile molto tranquillo, dove poter cenare e rilassarsi dopo una giornata passata tra le meraviglie naturali, storiche ed artistiche della zona. Ogni stanza di Umberto121 è differente dall'altra, avendo mantenuto le caratteristiche di ognuna.

Top guest favorite

A swimming pool reflects the clear blue sky, surrounded by natural landscapes with rolling hills in the background. Lush greenery and distant structures are visible along the horizon, enhancing the serene outdoor setting.

Vacation home in San Giovanni d'Asso

4.93 out of 5 average rating, 102 reviews

Elegant house with pool, Valdorcia Deluxe 1

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

Top guest favorite

A rustic stone house is set amidst lush greenery, featuring large windows that invite natural light. The structure includes a covered terrace adorned with climbing plants, providing an inviting outdoor space. The surrounding lawn is well-maintained, contributing to a peaceful rural setting.

Vacation 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 favorite

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.

Vacation home in Massa Marittima

4.94 out of 5 average rating, 96 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

Guest favorite

A spacious kitchenette and dining area is presented, featuring wooden cabinets and a gas stove. A wooden table with four chairs occupies the center, while a green sofa sits against the wall. Natural light filters through a nearby window, illuminating the terracotta floor.

Vacation home in Roccastrada

5 out of 5 average rating, 21 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 favorite

A simple bedroom is presented with a spacious bed, featuring decorative pillows in warm tones. A mirror reflects a clothing rack and a framed photograph adorns the wall. Natural light enters through a window, enhancing the neutral color palette.

Vacation home in Montemerano

4.94 out of 5 average rating, 31 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.

Guest favorite

A rustic stone farmhouse is gently illuminated at dusk, showcasing its architectural details against a twilight sky. Tall cypress trees frame the building, while soft lights outline the windows and entrance, creating a peaceful ambiance amidst the expansive countryside.

Vacation home in Monte Cucco

4.82 out of 5 average rating, 38 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 view of the hills all around. Imagine yourself with a glass of Brunello or Montecucco, Italian bites at hand, looking at 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.

Top guest favorite

A balcony view showcases a charming wooden table and two chairs, overlooking the harbor filled with boats. The scene is framed by glass doors and a lush green plant, enhancing the sense of openness and tranquility.

Vacation home in Porto Ercole

4.98 out of 5 average rating, 51 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

A sunlit terrace features two lounge chairs positioned on green grass, overlooking the expansive blue ocean. A wooden dining table is set nearby, framed by views of hills and a clear sky with scattered clouds.

Vacation home in Porto Santo Stefano

4.84 out of 5 average rating, 37 reviews

Sunny Seaside Cottage

In Monte Argentario, on the stretch of coast that connects Porto Santo Stefano to Porto Ercole, overlooking the sea and with a stunning view of the islands of Giglio and Giannutri, there is this charming autonomous two-room apartment, completely isolated from the view of other homes and the road It consists of a double bedroom, living room with spacious kitchenette and sofa bed , bathroom with shower. In the garden area equipped with barbecue, oven

Top guest favorite

An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.

Vacation home in Monticchiello

4.97 out of 5 average rating, 108 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Guest favorite

A vintage blue e-bike is parked near a rustic stone archway, showcasing the texture of the stones and the inviting entrance. Delicate vines and flowers gently adorn the wall, enhancing the overall charm of the setting.

Vacation home in Verziliani

4.91 out of 5 average rating, 69 reviews

The Little Verziliani House

Relax and recharge your batteries in this oasis of tranquillity and elegance, an ancient Templar stopover, immersed in the scenic Maremma hills, in a strategic position to reach the Saturnia Thermal Baths and all the area's attractions, even on an e-bike: ideal for a romantic weekend or to switch off and enjoy pure air, silence, nature and sport in total autonomy and with whoever you want.