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Vacation rentals in Cupi

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Top-rated vacation rentals in Cupi

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

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Superhost
A spacious yellow building is surrounded by well-maintained greenery and trees. The structure includes a balcony on the upper level, while the lower section features a covered porch area. A paved pathway leads to the entrance, providing a welcoming access to the property.
Home in Grosseto

Casa Allegra

Independent apartment on the ground floor of a farmhouse surrounded by nature, on the edge of the Maremma Regional Park and a few kilometers from the sea. Convenient location for discovering the Maremma, between Argentario and Punta Ala. It is possible to visit Rome, Florence, Siena and Pisa, which are well connected by train and bus.​It consists of a living area with a kitchen and sofa bed, a double bedroom, and a bathroom with a window and shower. There is a large garden with a BBQ, table, and deck chairs for relaxing. Adjacent to the bike path (Magliano-Parco Maremma).

FamilyValueBreakfast

4.84 out of 5 average rating, 95 reviews
Top guest favorite
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

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

ValueLocationView

4.93 out of 5 average rating, 294 reviews
Superhost
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

LocationValueKitchen

4.92 out of 5 average rating, 628 reviews
Superhost
An outdoor dining area is situated under a thatched roof gazebo, overlooking the ocean. A wooden table is surrounded by several matching chairs, creating a serene space for meals. Lush greenery frames the area, while the beach and water are visible in the background.
Villa in Giannella

Beach House Giannella w/ direct access to the sea

The villa is surrounded by a 1500 sq m garden with pines, Mediterranean plants and flowers, and includes a private sandy beach directly bordering the sea.It is composed of a living room, a kitchen, two double bedrooms, a bedroom with a bunk bed and two bathrooms (one of which in a small external structure). It is provided with air conditioning and a heat pump.In the park, there is an outdoor kitchen and a large table under a gazebo on the beach, which allows you to eat right in front of the sea.

FamilyValueLong stay

4.82 out of 5 average rating, 99 reviews
Guest favorite
A scenic view captures a serene outdoor area featuring a turquoise swimming pool, surrounded by sun loungers and lush greenery. Rolling hills and fields stretch into the distance, complementing the clear sky adorned with soft clouds, creating a peaceful countryside atmosphere.
Farm stay in Manciano

Casa Olivia: Comfort, Nature and Landscapes of Maremma

Placed in the Manciano countryside, in the intact landscape of South Tuscany, 20 min from the Saturnia Cascades, Casa Olivia is an apartment in a farmhouse in the center of an age-old olive grove. From the garden and the house you can enjoy an incredible view on the Maremma hills with the Argentario coast in the background. Uncontaminated nature, peace and a wide choice of excursions in the surrounding area between art, history, sea and traditions. 30 minutes from beaches and beautiful villages

FamilyLocationDecor

4.97 out of 5 average rating, 97 reviews
Superhost
A sun-drenched terrace offers a view of the sea, bordered by well-maintained gardens featuring colorful flowers. A dining table with chairs sits on the stone patio, complemented by two lounge chairs. The rustic villa's wooden doors provide access to the interior.
Villa in Talamone

Villa Il Molinaccio with terrace and private beach

Spacious rustic villa with a terrace overlooking the sea and access via stairs to a small pebbly beach. Ample outdoor and indoor spaces with garden. It has sun beds, sun umbrella, table tennis and barbecue. Recently purchased kitchen and furniture. A 10-minute walk from the harbour and centre, offering privacy but accessibility to all amenities like beaches, windsurfing, diving, and boat hire. Private garage in front of the house on private road. Recently renovated. Vintage and maritime style.

FamilyLocationSleep quality

4.9 out of 5 average rating, 97 reviews
Top guest favorite
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.
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.

LocationFamilyLaundry

4.97 out of 5 average rating, 252 reviews
Top guest favorite
A light-filled living area features large glass windows, offering views of the surrounding nature. An orange armchair and a minimal dining table are visible, complemented by wooden cabinetry and kitchen appliances. Natural light illuminates the space, enhancing the warm tones of the decor.
Home in Marrucheti _ Campagnatico

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.

LocationFamilyHospitality

4.98 out of 5 average rating, 181 reviews
Guest favorite
An infinity pool extends into the horizon, revealing sweeping views of the Tuscan landscape. Surrounding greenery and a paved patio are visible, with two lounge chairs positioned for relaxation. Soft natural light casts a tranquil ambiance across the scene.
Apartment in Campagnatico

Suite

A 45sqm house, separated from the main complex. Ideal for romantic getaways. It consists of: one bedroom, bathroom and living room with an open space kitchen. It includes: A sofa bed in the living room, which can be used as an extra bed. Bed linen, bathroom towels and beach towels Cleaning services halfway through the week.

FamilyLocationHospitality

5.0 out of 5 average rating, 70 reviews
Guest favorite
The villa's exterior showcases a charming Mediterranean-style design, featuring a terracotta roof and soft pink walls. The surrounding well-maintained lawn is bordered by tall trees, providing a serene backdrop, while outdoor seating is positioned on the patio, inviting relaxation.
Villa in Grosseto

Podere la Pompa

Villa with three bedrooms with ensuite bathroom, large kitchen and living room. External loggia for outdoor dining and possibility of using the shared swimming pool. Piccola Pompa is located a short drive from Grosseto and less than 20 minutes from the beaches of Castiglione della Pescaia

LocationFamilySleep quality

5.0 out of 5 average rating, 27 reviews
Guest favorite
A panoramic view of rolling hills is displayed, featuring lush green fields and scattered trees. The landscape stretches into the distance, with a clear blue sky overhead, providing a serene natural backdrop. The foreground includes unpaved pathways and rocks.
Home in Orbetello

House in the Maremma countryside with a view of Argentario

House in the countryside, first floor, with a large terrace overlooking the hills of the Tuscan Maremma, Argentario. Large garden with private parking. All within a bio-agricultural and livestock farm. We accept pets for a supplement of €15 to be paid directly at check-in.

LocationFamilySleep quality

4.9 out of 5 average rating, 235 reviews
Top guest favorite
The illuminated village of Pitigliano is captured at dusk, showcasing its distinct stone buildings and rooftops. The historic tower stands prominently in the background, while soft lights line the streets, creating a serene atmosphere in the valley below.
Condo in Pitigliano

Panoramic penthouse in the ancient village

Penthouse with two panoramic terraces with stunning views of the valley and the historic center, in the square below the historic Orsini Fortress. Twenty minutes from the Terme di Saturnia and five minutes from the Terme di Sorano, immersed in the Maremma landscape.

FamilyLocationGetting around

4.94 out of 5 average rating, 465 reviews

Popular amenities for Cupi vacation rentals