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Holiday rentals in Grosseto

Find and book unique accommodation on Airbnb

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
Flat in Caminino
4.92 out of 5 average rating, 193 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.

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 130 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favourite
Guest house in Macciano
4.97 out of 5 average rating, 221 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
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, 151 reviews

caratteristico centro storico A. & G.

L' alloggio indipendente 3 posti letto nel centro storico di Grosseto. A 100 metri vi è un ampio parcheggio gratuito fuori le mura medicee, (all'interno delle mura è severamente vietato l'accesso alle auto non autorizzate). vicino all'alloggio vi sono minimarket, farmacia, 800 metri la stazione ferroviaria, autobus per il mare e navetta per Stazione. punto di partenza per: mare 14 km, 60 km terme di saturnia, 14 km dal parco naturale della Maremma, 50 km Monte Argentario, e Siena a 70km.

Top guest favourite
An aerial view captures a serene farmhouse surrounded by rolling hills. A curving dirt road leads to the home, bordered by tall cypress trees. Soft sunlight bathes the landscape, highlighting the lush greenery and distant mountains.
Farm stay in Campiglia D'orcia
4.92 out of 5 average rating, 586 reviews

Agriturismo Poggio Bicchieri ap. Memoria

Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!

Top guest favourite
A serene outdoor space features a lit jacuzzi next to a lounge chair on a wooden deck. The stone walls of the nearby building provide texture, while distant views of the sea are illuminated under the evening sky, enhancing the peaceful ambiance.
Home in Rio Marina
5 out of 5 average rating, 106 reviews

Casa del Capitano | 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
An ancient stone building is showcased, featuring arched doorways and multiple windows. The façade is adorned with climbing greenery, creating a blend of natural and architectural beauty. Cobblestones form the ground, contributing to a rustic and historic ambiance.
Flat in Civita
4.94 out of 5 average rating, 275 reviews

La Cava (Palazzo Pallotti)

L'appartamento é due piani sotto la piazza, interamente scavato nel tufo. Con vista sulla valle, é isolato dai rumori della strada, tranquillo, privato e molto accogliente. Le pareti in tufo gli donano un'aria antica, per trasportavi altrove nel tempo. Si raggiunge a piedi, attraverso un ponte pedonale che vi porta direttamente nella piazza dove c'é l'immobile. É perfetto per brevi soggiorni di completo relax, ma con la cucina totalmente attrezzata si sfrutta al massimo.

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.92 out of 5 average rating, 266 reviews

Casa al Gianni - Capanna

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Superhost
Apartment in Castelnuovo dell’Abate
4.9 out of 5 average rating, 314 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.

Top guest favourite
An outdoor terrace showcases vibrant potted flowers and a rustic wooden bench, extending along a stone wall. Lush greenery and breathtaking valley views are visible in the background under a clear blue sky.
Flat in Civita
4.98 out of 5 average rating, 489 reviews

L'Incanto di Civita (La Terrazza)

L'Incanto di Civita si trova all'interno dell'antico borgo di Civita di Bagnoregio. Lasciata la macchina al parcheggio si dovrà necessariamente procedere a piedi lungo il ponte, unica via di accesso alla nostra "perla di tufo". L'Incanto di Civita is located in the ancient hamlet of Civita di Bagnoregio. After leaving the car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Superhost
A serene outdoor space features rocky beach access with a kayak floating nearby. Comfortable lounge chairs are positioned on the terrace overlooking the sea, surrounded by coastal vegetation. The clear blue water reflects the sunlight, enhancing the tranquil atmosphere of the seaside setting.
Apartment in Porto Santo Stefano
4.83 out of 5 average rating, 210 reviews

Villa Rosetta, apt 2, Lovely beach historic house

A lovely apartment at the sea front, with direct access to the sea with rock beaches, surrounded by a beautiful mediteranean garden. You can relax on the beach in every moment. You can swim in the sea whenever you want. Welcomes well behaved dogs. There are extra cost in addition to the cost of the stay: cleaning fee, municipality tax, ZTL pass Follow us on @: villarosetta1914

Top guest favourite
Flat in Grosseto
4.95 out of 5 average rating, 193 reviews

Lollo Bilocale nel Centro Storico

Lollo AB è un piccolo bilocale per affitti brevi che può ospitare una o due persone, posto al primo piano (senza ascensore) di un palazzo storico all’interno delle mura Medicee della città di Grosseto. Dotato di tutti i comfort è ideale per soggiorni di lavoro e vacanza. A soli 10 minuti di auto dal mare, a un'ora dal Monte Amiata e dalle famose Terme di Saturnia.

Popular amenities for Grosseto holiday rentals

When is the best time to visit Grosseto?

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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 3,650 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

    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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