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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, 110 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
A bright double bedroom is presented with a spacious bed featuring crisp white linens. Natural light floods the room through an open window, framing a view of the surrounding valley. Wooden beams add character to the ceiling, and bedside tables with lamps are positioned beside the bed.
Holiday home in Montepulciano
4.92 out of 5 average rating, 191 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
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.
Holiday home in Monticchiello
5 out of 5 average rating, 24 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
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.
Holiday home in Massa Marittima
4.93 out of 5 average rating, 107 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 favourite
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.
Holiday home in Roccastrada
5 out of 5 average rating, 26 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
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.
Holiday home in Montemerano
4.92 out of 5 average rating, 38 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 favourite
A welcoming living area features a wooden dining table surrounded by chairs, with a cozy sofa adorned with cushions and a fireplace to one side. Natural light enters through a window overlooking greenery, highlighting stone walls and rustic wooden beams.
Holiday home in Pitigliano
5 out of 5 average rating, 14 reviews

Independent Historic Sweet House on the Walley.

Rilassati e ricaricati in quest'oasi di quiete ed eleganza nel centro storico di Pitigliano, all’interno della Piccola Gerusalemme con vista sul verde della vallata. Adatto alle famiglie con la zona giorno, l’angolo cucina e l’ampia zona notte al piano superiore. Siamo pet friendly 🐶❤️ Il bagno, da poco ristrutturato, e’ confortevole con una comoda doccia a parete 70x120, l’angolo lavabo dalla parte opposta. Adatto anche per lo smart-working con un angolo lavoro e Wi-Fi illimitato.

Superhost
A large swimming pool is surrounded by lush greenery and olive trees. Rolling hills and vibrant vegetation are visible in the background, creating a serene outdoor space for relaxation. Sun loungers are positioned around the pool, inviting guests to enjoy the scenic views.
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
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.
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.

Top guest favourite
A contemporary suite is presented with a sleek exterior design, featuring large windows and a shaded terrace. A private hot tub is positioned on a stepped platform, surrounded by greenery. A shaded seating area with an umbrella is visible, along with outdoor lounging options.
Holiday home in Scarlino
5 out of 5 average rating, 15 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
The exterior of a multi-story brick building is surrounded by lush greenery and vibrant foliage. Windows with dark shutters are visible, and ornamental plants on the balcony add a touch of color. The building is nestled within a scenic landscape.
Holiday home in Torrenieri
4.96 out of 5 average rating, 74 reviews

VACATION HOME I DUE CIPRESSI "Rosa Canina Apartment"

The Rosa Canina apartment is located in Torrenieri (SI), a small hamlet of the municipality of Montalcino, equipped with every comfort to spend a relaxing vacation or for work commitments. Great location for visiting the beautiful villages of Val d'Orcia, such as San Quirico d'Orcia, Pienza, Montepulciano, etc. And for those who want to venture out, you can walk the Via Francigena, a 5-minute walk away, enjoying the wonderful Tuscan landscapes.

Top guest favourite
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.
Holiday home in Monticchiello
4.97 out of 5 average rating, 118 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.

Popular amenities for holiday home rentals in Grosseto

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