Vacation rentals in Grosseto

Condo in Porto Santo Stefano

A terrace is visible through an open door, featuring a wooden dining table surrounded by chairs. A small vase with flowers rests at the center of the table. The background showcases a panoramic view of the sea and a clear sky.

4.88 out of 5 average rating, 204 reviews

Charming apartment with breathtaking sea views

Charming apartment with breathtaking sea views. The property includes a spacious kitchen, a bathroom, a bedroom with a double bed, a second bedroom with two single beds that can also be used as a living room, and a terrace equipped with a table and loungers: perfect for relaxing with a stunning sea view! Spacious wardrobe closet in each room, fiber optic Wi-Fi, air conditioning, a large private parking area and a private shortcut that connects directly to the town (just a 5/10 minute walk away).

4.96 out of 5 average rating, 165 reviews

Guesthouse in Macciano

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.

4.96 out of 5 average rating, 121 reviews

A wooden table displays two elegant wine glasses beside an open bottle of red wine. A twisted piece of driftwood adds a rustic touch. In the background, expansive green hills are visible under a clear blue sky, inviting relaxation.

Cottage in Vetulonia

La Dolce Vita ~ romantic retreat in quiet nature

Welcome to Il Baciarino! We are a rustic agriturismo in the green hills of Maremma, Toscana's wild and unexplored coastal region. Il Baciarino is a place to come and stay, to escape from the bustle of the city and your busy life, and to unwind in nature; perfect for those who love unspoiled nature, endless views, fresh seafood & good wine. Il Baciarino has various unique rustic cottages nestled in 19 acres of wilderness, on the outskirts of the tiny Etruscan town of Vetulonia.

Cottage in Castell'Azzara

The kitchen area features wooden cabinets and modern appliances, including a gas stove and oven. A round table with a colorful design is surrounded by black wire chairs. Large windows provide natural light and views of the surrounding landscape.

4.99 out of 5 average rating, 139 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

4.99 out of 5 average rating, 243 reviews

Farm stay in Seggiano

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.

Apartment in Montepulciano

A wooden balcony table is set for tea, featuring delicate china cups accompanied by cookies. A simple vase holds fresh flowers. The stunning countryside view stretches across rolling hills under a clear sky, enhancing the serene atmosphere of the outdoor space.

4.94 out of 5 average rating, 196 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historical center offers a breathtaking view of the surrounding countryside, giving an authentic and unforgettable experience. You can leave the house and taste the historic atmosphere of Montepulciano. Within walking distance you will have the extraordinary Piazza Grande, high quality restaurants and services of all kinds. Tuscany awaits you to experience unique emotions.

4.93 out of 5 average rating, 119 reviews

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Condo in Castelnuovo dell’Abate

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

4.91 out of 5 average rating, 288 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.

4.99 out of 5 average rating, 128 reviews

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

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

Condo in Porto Santo Stefano

A clear, calm sea gently laps against rocky shorelines. The water reveals visible seaweed and pebbles beneath the surface. A verdant hillside rises above, featuring a building surrounded by pines, with a blue sky and distant hills in the background.

4.83 out of 5 average rating, 202 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

4.89 out of 5 average rating, 198 reviews

A spacious green garden is visible, dotted with trees offering natural shade. A wooden dining table with chairs is positioned under the trees, providing an inviting setting for outdoor meals. The rustic brick building stands in the background, complementing the serene surroundings.

Farm stay in Simignano

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!

4.98 out of 5 average rating, 144 reviews

Home in Marrucheti

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Bungalows

Intimate homes. inviting architecture

Villas

Luxurious estates for the ultimate escape

Popular amenities for Grosseto vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Grosseto

4.91 out of 5 average rating, 77 reviews

A rustic stone house is set against a backdrop of lush trees, featuring a terrace with sun loungers arranged around a central swimming pool. The building's earthy tones complement the natural surroundings, while a chimney adds a touch of charm to the exterior.

Cottage in Roccalbegna

Small cottage, swimming pool entirely private use

MilliRating, 5 stars1 week ago

What a fabulous place - if you want to escape from it all, this is the place to come! Love the private pool too! Air conditioning in the bedroom was very good and appreciated. Olga and Max were very accommodating and answered questions very quickly. Maybe consider installing a BBQ outside the house otherwise could not fault it and we cannot wait to return!

4.96 out of 5 average rating, 50 reviews

The image captures a stone building with a terracotta roof, featuring a tall cypress tree set against a vast landscape. Rolling hills and olive groves extend into the distance under a clear sky, with soft afternoon light illuminating the scene.

Home in Montemassi

Capezzuolo 33

BenRating, 5 stars2 weeks ago

This apartment was so beautiful and the views were even better. We had an amazing stay here as our base for exploring Tuscany - visiting the Val d’Orcia and the thermal baths were a highlight! Lucia and Marco met us on arrival and were extremely friendly and gave us plenty of advice and places to visit. There was an issue with the boiler but Lucia was straight on it and it was fixed by the time we were home for the day. Thank you so much!

Apartment in Marina di Grosseto

A sandy pathway leads to the beach, framed by coastal vegetation. On one side, low shrubs and a small tree provide natural accents, while a beachside structure is seen in the distance. The scene captures a tranquil coastal environment during the golden hour.

4.64 out of 5 average rating, 11 reviews

Sea Pearl

NicoleRating, 5 stars9 months ago

We felt very comfortable at the place and especially enjoyed the terrace with the barbecue! The apartment is also a stone throw away from the beach. Franca was also very friendly and helpful :)

Tower in San Quirico d'Orcia

A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.

5 out of 5 average rating, 87 reviews

Luxurious Medieval Tower & Private Concierge

MatthewRating, 5 stars2 weeks ago

Can’t recommend this enough. Beautiful and unique accommodations in a picturesque setting. Leonie and Nico and their family are wonderful, and make you feel like part of a local family in Tuscany. We will definitely be back one day.

Cottage in Osteria delle Noci

A dining table is set for a meal, featuring plates and glasses neatly arranged. Large glass doors offer a view of the surrounding landscape, including green hills and distant mountains. Natural light fills the space, enhancing the rustic wooden details.

5 out of 5 average rating, 95 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

SamRating, 5 stars4 days ago

This beautiful, private, peaceful property is a must-stay if you're in the area. Breathtaking views out of every window. Short drive to a few nearby towns with great food and wine.

4.9 out of 5 average rating, 10 reviews

A balcony showcases two white chairs positioned to enjoy views of the surrounding landscape. The scene includes a historic building with a green dome and a tall spire, framed by a clear blue sky dotted with clouds.

Condo in Grosseto

Penthouse 203 - Grosseto - Large - Panoramic Terrace

AilenRating, 5 stars1 month ago

We stayed in this apartment in Grosseto for a full month, and the experience exceeded our expectations. The apartment was spacious, clean, and cozy – a perfect place to combine vacation and remote work. Everything we needed was provided. The location was peaceful, yet conveniently close to shops, cafes, and the old town. The apartment had a genuine Italian charm, with tasteful and homey interior design. Our host Ivan was simply outstanding – always friendly, responsive, and eager to share helpful tips about what to see and do in the area. Thanks to his recommendations, we discovered places we might have otherwise missed. We highly recommend this accommodation to anyone looking for a quiet, comfortable, and authentic place to stay for an extended visit. A big thank-you to Ivan for the warm welcome and excellent hospitality!

4.96 out of 5 average rating, 23 reviews

Condo in Grosseto

Apartment in villa with garden and parking space

LohRating, 5 stars4 months ago

Luca provided an exceptional service and great accommodation.