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Holiday rentals in Grosseto

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Top-rated holiday rentals in Grosseto

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Top guest favourite
Flat in Caminino
4.91 out of 5 average rating, 184 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat in Montepulciano
4.97 out of 5 average rating, 130 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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
4.89 out of 5 average rating, 144 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
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay in Seggiano
4.99 out of 5 average rating, 267 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Guest favourite
A living area features a pink accent wall complemented by white and black modular storage units. A television is placed on a low white media console. A patterned area rug adds texture, while natural light enters through a large window with a curtain.
Apartment in Grosseto
4.9 out of 5 average rating, 100 reviews

The first nest

Charming two-room apartment located on the second floor near the Medici walls, the historic center and the train station. Equipped with all comforts, it is ideal as a starting point for excursions to the Maremma coast, Mount Amiata, Saturnia, Siena and Val d'Orcia. Possibility to leave the car in the private condominium parking lot in the basement of the building. A few steps away, there is a supermarket and a small local market where you can buy fruit, vegetables and fish.

Top guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 103 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Top guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Flat in Montemassi
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

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, 115 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.

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
4.96 out of 5 average rating, 102 reviews

Casetta Venere relaxing Tuscan 3 km from the sea

Venus cottage: 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 animals. The house offers curated spaces, a beautiful private garden, and an intimate and welcoming atmosphere. We are waiting for you for a slow, authentic and beautiful stay in the middle of nature.

Guest favourite
A compact dining area features a wooden table set for two, accompanied by a white chair. A floral-patterned sofa adds a touch of color, while a potted plant provides a natural element. Bright light enters through a large window adorned with sheer white curtains.
Apartment in Grosseto
4.85 out of 5 average rating, 152 reviews

Ale's little house

The renovated apartment is located in the historic center, has an independent entrance on the street floor inside a historic building. You can park your car in the immediate vicinity in free and/or paid parking. Thanks to its favorable location, you can visit the city without having to use a car. There is also a drinking water purifier inside the apartment. unlimited ultra-fast WiFi

Top guest favourite
A charming stone house is surrounded by lush greenery and colorful flowers. The exterior features a thatched roof and several wooden windows, with a seating area adorned with potted plants. Mature trees provide shade, creating a peaceful outdoor atmosphere.
Home in Pancole
4.99 out of 5 average rating, 143 reviews

Casa Pancole

Beautiful stone house completely and tastefully renovated, surrounded by nature, ideal for privacy, close to places of interest such as Grosseto, Terme di Saturnia, Alberese, Parco dell'Uccellina, Marina di Grosseto (in the cold periods there is a pellet stove that heats the rooms, the pellet is an additional cost to be requested, thank you) tourist tax to be paid directly on site

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
4.95 out of 5 average rating, 183 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$93 SGD$96 SGD$103 SGD$116 SGD$116 SGD$120 SGD$135 SGD$141 SGD$122 SGD$105 SGD$100 SGD$99 SGD
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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.

Quick stats about holiday rentals in Grosseto

  • Total holiday rentals

    Explore 130 holiday rentals in Grosseto

  • Nightly prices starting at

    Grosseto holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    100 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!

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