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Holiday rentals in Grosseto

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Grosseto

  • Total holiday rentals

    Explore 120 holiday rentals in Grosseto

  • Nightly prices starting at

    Grosseto holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,830 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    90 of Grosseto holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grosseto rentals

  • 4.8 Average rating

    Grosseto stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Grosseto

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Villa in Chianciano Terme
4.97 out of 5 average rating, 126 reviews

Charming Tuscan Villa with View forFamily&Friends

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 231 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favourite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 110 reviews

Captain's House | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Top guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 167 reviews

Casa Dolce Toscana | Panoramic Suites & Views

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 313 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
The image depicts a historic building with a prominent bell tower, characterized by its tall spire and intricate brickwork. A sky filled with clouds in various shades of blue and purple provides a serene backdrop, complementing the architectural details of the structure.
Apartment in Grosseto
4.9 out of 5 average rating, 159 reviews

Characteristic old town A. & G.

The independent 3-bed accommodation in the historic center of Grosseto. 100 meters away there is ample free parking outside the Medici walls, (access to unauthorized cars is strictly prohibited inside the walls). Near the accommodation there are a minimarket, pharmacy, 800 meters from the train station, bus to the sea and shuttle to the station. Starting point for: sea 14 km, 60 km Saturnia thermal baths, 14 km from the Maremma Natural Park, 50 km Monte Argentario, and Siena 70 km.

Top guest favourite
A spacious bedroom features a large, inviting bed adorned with a light blanket. Natural light floods through sheer curtains draped over a large window, revealing views of the lush valley outside. The rustic walls, made of tufo, add a unique character to the room.
Flat in Civita
4.94 out of 5 average rating, 286 reviews

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

Guest favourite
The kitchen features a modern design with a combination of light and dark cabinetry. An equipped countertop includes a sink, stove, and microwave, while patterned tiles add texture. A rug in warm colors lies underfoot, complementing the wood-paneled ceiling that enhances the cozy atmosphere.
Flat in Grosseto
4.9 out of 5 average rating, 145 reviews

Carla's house

The renovated loft is a 5-minute walk from the historic center and 5 minutes from the station. It has a separate entrance on the ground floor. Free parking is available. It has a double loft bed, double sofa bed (crib on request), linen, equipped kitchen, bathroom with shower and window, independent heating and air conditioning. On the street, there is a bar, take-out pizzeria, coin-operated laundry, hairdresser, rotisserie. Adjacent pharmacy, supermarket.

Superhost
A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.
Apartment in Castelnuovo dell’Abate
4.9 out of 5 average rating, 320 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Guest favourite
A charming stone cottage is depicted, featuring a dark roof and a welcoming entrance. Vibrant purple flowers in the foreground provide a splash of color against the gravel pathway, while warm sunlight casts a gentle glow, highlighting the serene surroundings.
Flat in Castiglione della Pescaia
4.95 out of 5 average rating, 138 reviews

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families, and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay in the midst of nature.

Top guest favourite
A small stone alcove features a wooden table with a potted flower and two red folding chairs. The background reveals a serene view of lush hills, creating a quiet space for relaxation.
Flat in Civita
4.98 out of 5 average rating, 500 reviews

The Enchantment of Civita (The Terrace)

L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Top guest favourite
A cozy living area is showcased, featuring a patterned sofa and a wooden dining table set for two. Natural light enters through a sheer curtain, highlighting the light hardwood floor. Kitchen appliances and storage cabinets are neatly arranged along one wall.
Flat in Grosseto
4.96 out of 5 average rating, 200 reviews

Lollo Two-Room Apartment in the Historic Center

Lollo AB is a small two-room apartment for short rentals that can accommodate one or two people, located on the first floor (no elevator) of a historic building within the Medici walls of the city of Grosseto. Equipped with all the comforts, it is ideal for business trips and vacations. Just a 10-minute drive to the sea, an hour to Monte Amiata and the famous Terme di Saturnia.

Popular amenities for Grosseto holiday rentals

When is the best time to visit Grosseto?

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Avg. price$116 SGD$122 SGD$119 SGD$116 SGD$116 SGD$120 SGD$136 SGD$142 SGD$123 SGD$115 SGD$111 SGD$120 SGD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C

Frequently Asked Questions

  • What are the best places to stay in Grosseto?

    The historic center draws visitors with its walkable lanes and access to local dining. Rural stays around the Maremma countryside have tranquil settings, while accommodations near the coast are frequently suggested for those preferring beach access.

  • What are the best things to do in Grosseto with kids?

    Families frequently suggest exploring the city walls, visiting interactive exhibits at the local natural history museum, and playing at public gardens around the center. Beaches and nature reserves near Grosseto also have nature trails suitable for children.

  • What are some of the best things to do in Grosseto?

    Explore the Medicean Walls, discover the Cathedral of San Lorenzo, and visit the Archaeological Museum for insights into Etruscan history. Enjoy local cuisine at traditional trattorias and stroll bustling markets in the city center.

  • How is the weather in Grosseto?

    Grosseto has mild winters around 37–55°F (3–13°C) and warm, dry summers reaching 89°F (32°C). Rainfall is lightest from June to August, with autumn and late winter months seeing more frequent showers.

  • When is the best time to visit Grosseto?

    Late spring and early autumn are often recommended, with milder temperatures and less rain, making it enjoyable for outdoor activities and cultural events. Summer brings warmer weather for beach visits around the region.

  • What are the best places to visit in Grosseto?

    Explore the Medicean Walls, the Cathedral of San Lorenzo, and the Archaeological Museum for highlights of Grosseto’s heritage. Nature lovers often gravitate toward Maremma Regional Park or the Orbetello Lagoon for distinct Tuscan landscapes.

  • What are some hiking trails in Grosseto?

    Grosseto’s surroundings have scenic hiking options through the Maremma Regional Park, shaded woodlands, and coastal paths with views of the sea. Many trails highlight both local wildlife and historical landmarks along the way.

  • What are some family activities we can do in Grosseto?

    Explore the historic center with its city walls, discover interactive natural history museums, and enjoy local parks with playgrounds or organized outdoor activities. The coastline near Grosseto also has beaches with calm shallows for younger children.

  • What are some of the best day trip ideas from Grosseto?

    Explore the medieval villages scattered across the Maremma countryside, visit relaxing hot springs around southern Tuscany, or discover coastal nature reserves known for wildlife and scenic trails. Vineyards and olive groves in the region provide opportunities to experience local flavors.

  • Are there any pet friendly accommodations available in Grosseto?

    Many local stays have pet-friendly options, including apartments in the historic center and agriturismo-style retreats around the countryside. Parks and nature reserves in the area make it easy to explore Grosseto with your pet.

  • What are some local tips for visiting Grosseto?

    Embrace the local pace by stopping for an espresso in the morning and browsing small markets for regional products. Many travelers seek out countryside trattorias for authentic meals, and joining in evening strolls through piazzas is a cherished local tradition.

  • What is Grosseto known for?

    Grosseto is known for its historic old town with preserved medieval walls, Etruscan and Roman heritage, and landscapes marked by the Maremma countryside. The area also gains recognition for traditional Tuscan cuisine and outdoor activities.

  • What are the best hidden gems to explore in Grosseto?

    Wander the city’s ancient walls and search for artisan shops tucked into quiet lanes around the historic center. Small museums, family-run trattorias, and nearby nature reserves are frequently suggested by locals for a deeper sense of place.

  • What are the best foods to try in Grosseto?

    Grosseto has traditional Maremman dishes such as wild boar stew, acquacotta soup, and handmade pici pasta. Local cheeses, olive oil, and sweet cantucci biscuits paired with dessert wine are frequently suggested specialties.

  • What should I bring for a trip to Grosseto?

    Pack comfortable walking shoes for exploring the old town and countryside, along with lightweight clothing for warm summers or a jacket for cooler winters. Sunglasses, sunscreen, and a reusable water bottle are often suggested, as well as a power adapter for electronics.

  • What is the nightlife in Grosseto like?

    Grosseto’s nightlife is centered around cafes and wine bars in the old town, where locals relax with aperitifs and small bites. There are often live music nights at neighborhood venues, and many enjoy socializing in lively piazzas on warm evenings.

  • What are the most popular events or festivals in Grosseto?

    Grosseto has a lively medieval fair in the historic center, traditional food and wine festivals in late summer, and music events often scheduled in main piazzas. Local cultural celebrations showcase regional traditions and seasonal harvests.

  • Are there family friendly vacation rentals in Grosseto?

    Grosseto has a variety of family-friendly vacation rentals, including apartments with kitchens, countryside homes, and stays near playgrounds or local parks. Many listings feature amenities like extra bedrooms and outdoor space for families.

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