
Holiday rentals in Grosseto
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Top-rated holiday rentals in Grosseto
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

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.

Le Antiche Viste - The Zen Terrace
Enjoy the tranquillity and the stunning views. Treat yourself to an aperitivo on the terrace, and relax in the zen living room. A stylish 100 sq m gem just for you, with 1.5 bathrooms, TV, kitchen, and fast wi-fi for remote working. Perfect for a couple (or a solo traveller). Bedroom is equipped with air conditioning! If you're passionate about combating climate change, you can opt for the ceiling and floor fans available in every room. They ensure a refreshing stay, even on the warmest days.

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

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.

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.

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.

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

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

La Stallina - Perfect retreat from the city rush
Recently restored, La Stallina, was my grandfather's horse stable at the beginning of last century. Now it is a charming apartment perfect for a couple and suitable for 2+2 guests. One living room with kitchen in a conservatory, double bed and mezzanine with bed. Bathroom with large shower box, kitchen equipped with dish-washing and oven.

Studio 1700 historic center Top for Singles
28 sqm small loft. CHECK-IN FROM 16h00 pm CHECK-OUT MAX 11hoo am SELF CHECK-IN Wood parquet, TV, clima converter. Suitable for experiencing something different than usual. Accommodation is suitable for young people, singles. Few nigts only. 28 steps to the first floor, rather steep but feasible. TIP: light baggage :-)
Popular amenities for Grosseto holiday rentals
Other great holiday rentals in Grosseto

Glamping The Garden of San Giorgio "Armida"

Carlino's Little House

Proceno Castle, Loggia Apartment

Cipressini 2 - pool and amazing views

The twigs

Panoramic penthouse in the ancient village

Casa Olivia: Comfort, Nature and Landscapes of Maremma

Podere la Pompa
Quick stats about holiday rentals in Grosseto
Total rentals
120 properties
Nightly prices starting at
$52 SGD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
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- Elba
- Giglio Island
- Lake Bolsena
- Giannutri
- Feniglia
- Cala Violina
- Gulf of Baratti
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Zuccale
- Spiaggia Marina di Cecina
- Cala Di Forno
- Spiaggia di Marina Di Campo
- Marina di Grosseto beach
- Riva del Marchese
- Spiaggia di Cavo
- Castiglion del Bosco Winery
- Le Cannelle
- Golf Club Toscana
- CavallinoMatto