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Vacation rentals in Cupo

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Top-rated vacation rentals in Cupo

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Guest favorite
The outdoor infinity pool is surrounded by lush greenery and features comfortable lounge chairs. Umbrellas provide shade for relaxation. The tranquil setting offers panoramic views of the surrounding hills and clear blue skies, inviting guests to enjoy a serene outdoor experience.
Villa in Cagli
5 out of 5 average rating, 13 reviews

[Doge's Palace Urbino] Villa with Swimming Pool

Welcome to Tenuta Ca Paolo, an authentic Marche farmhouse nestled in a 50-hectare agricultural estate. Here, nature reigns supreme among centuries-old forests, a truffle field, a private lake and rolling hills, offering you a haven of peace and relaxation away from the chaos of the city, but just a few minutes' drive from some of the most fascinating places in the Marche region: the beautiful Urbino, a UNESCO World Heritage Site, the spectacular Furlo Gorge, and the golden beaches of Fano, which can be reached in just 20 minutes.

Top guest favorite
The image shows a historic villa with a stone façade and a prominent tower. The property is surrounded by a well-kept lawn, with a clear pathway leading to the entrance. Lush greenery and decorative planters enhance the inviting appearance of the building.
Villa in Colombella
5 out of 5 average rating, 103 reviews

Torre Villa Belvedere Luxury & Relax with pool

"TORRE VILLA BELVEDERE" Meraviglioso appartamento di 260 metri quadrati , in Villa del XII sec .La piscina privata ( lunga 15 metri e larga 5 metri ) ,biliardo, biliardino, freccette,ampio giardino , portico 80 mq, barbecue,palestra e area relax all'interno della Torre. Comodo parcheggio privato all'interno della struttura. Situato in posizione strategica ,12 Km da Perugia, 4km dalla superstrada,può ospitare comodamente fino a 8 ospiti 3 camere matrimoniali con bagno privato, Tv, cassaforte

Guest favorite
The villa is surrounded by lush greenery, showcasing an inviting infinity pool that reflects the sky. The stone exterior of the house features warm wooden shutters, with outdoor seating visible on the terrace. Nearby, lavender plants create a serene ambiance against the landscape.
Villa in Lisciano Niccone
4.88 out of 5 average rating, 50 reviews

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

Guest favorite
A saltwater pool is framed by lush greenery, with sun loungers placed beside it. The setting features rolling hills in the background under a partly cloudy sky, creating a serene atmosphere. Stone walls surround the pool area, enhancing the natural beauty of the location.
Villa in Perugia
4.91 out of 5 average rating, 33 reviews

Fattoriafontenovo, country house Perugia, Umbria

Welcome to our charming apartment in Fattoria Fontenovo in Umbria fresh hills !This cozy retreat at our historic Fontenovo Farm, owned by our family for over 100 years, offers the perfect blend of privacy and tranquility. Some areas of the spacious villa remain unoccupied and others are reserved for your use. During the stay, you'll be the sole occupants, apart from the owners who may occasionally be in another part of the house. Enjoy the lush gardens, private pool, and serene countryside.

Guest favorite
A serene outdoor area showcases a clear turquoise pool surrounded by smooth stone decking. Lush greenery extends beyond the pool, and a traditional villa with a rustic roof can be seen in the background, framed by trees and open fields.
Villa in Genga
4.97 out of 5 average rating, 31 reviews

AndreoliScipioniLoriana 4/8 Guests Exclusive pool

It is a beautiful 19th-century house, renovated, immersed in the quiet of Frasassi Park. In the garden, it has a 12m x 6m swimming pool, 1.20m to 2.50m deep, and a jacuzzi, reserved for the villa's guests. With its 10 beds, it is suitable for groups of friends, large families or 2 families. The kitchen is very well equipped, and in the veranda there is a fireplace/barbecue and a wood-burning oven. It is 10 minutes from Frasassi Caves, 6 km from Arcevia (An), 8 km from Sassoferrato (An).

Top guest favorite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari
4.99 out of 5 average rating, 258 reviews

Casa Rosmarino Eco-Wellness Country Home

Summer 2026 villas w/private pool available : airbnb.com/h/casaflavia10 airbnb.com/h/villaflaviaarezzo Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Guest favorite
A serene pool area is featured, with crystal-clear water reflecting the surrounding greenery. The rustic stone buildings in the background are framed by lush trees, while comfortable seating arrangements invite relaxation under the sun.
Casa particular in Matelica
4.89 out of 5 average rating, 18 reviews

I light up with immense

Enjoy a different vacation and regenerate your body and mind. Bring books to read under the mulberry trees. Walk through nature, breathing healthy air and traveling kilometers of countryside with organic crops while observing the landscape where nature has been able to create paintings. Relax with the whole family, living days with a different spirit and more attention to those close to you, in accommodation where serenity, atmosphere and nature make everything wonderfully unique.

Top guest favorite
A cozy living area is highlighted by a large stone fireplace and wooden ceiling beams, creating a warm ambiance. Two comfortable armchairs are positioned near a wooden table, complemented by decorative vases. A small bouquet of flowers adds a touch of color to the setting.
Condo in Gubbio
4.98 out of 5 average rating, 48 reviews

Dimora Iguvium · Gubbio historic center

A short walk from Piazza dei Consoli, the Iguvium Dimora is located in the historic center, at the foot of Mount Sant'Ubaldo. A spacious and very quiet home where you can stay in full relaxation. Guests will be able to walk to the most important monuments of this beautiful medieval town, located in the alleys, and stroll through the green Umbrian hills. The availability on request of the covered parking adjacent to the Residence is useful, allowing you to visit the nearby cities.

Top guest favorite
A spacious swimming pool is surrounded by well-maintained gardens with lush greenery and tall trees. Comfortable loungers are positioned on the pool deck, and an umbrella provides shade nearby. The tranquil setting offers views of the adjacent hills and landscape.
Villa in Assisi
4.95 out of 5 average rating, 42 reviews

Poggio Ginepro Panoramic Villa in Assisi

Beautiful villa with private pool and garden, set in a breathtaking landscape, just 5 minutes from the center of Assisi and a few meters from the FAI site "Il Bosco di San Francesco". The villa, on three floors, is tastefully furnished with carefully selected furniture, carpets and paintings. It has 4 double bedrooms on the first floor and a sofa bed, for a total of 10 beds. There are also 5 bathrooms on the various floors. The swimming pool is at a lower level of the garden.

Top guest favorite
The exterior of the stone annexe is showcased, surrounded by lush greenery. A shaded seating area is highlighted in front, with a small table and chairs beneath an umbrella. A pathway leads up to the entrance, nestled in a serene natural landscape.
Guesthouse in Perugia
4.99 out of 5 average rating, 140 reviews

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

Top guest favorite
The image depicts a serene pool area surrounded by lush Mediterranean greenery. A bright orange umbrella provides shade, while a well-maintained stone pathway leads to the entrance of a charming stone farmhouse in the background.
Home in Loc. Casalini - Comune Panicale
4.99 out of 5 average rating, 100 reviews

Cottage surrounded by nature

"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.

Top guest favorite
The aerial view showcases the elegant Guest House surrounded by well-manicured green landscapes, vineyards, and trees. A winding gravel driveway leads to the house, highlighting its rustic charm and tranquil setting amidst the rolling hills of the Marche region.
Farm stay in Cingoli
4.98 out of 5 average rating, 80 reviews

The Guest House of the Tavignano Estate

The Tavignano estate is located in the heart of the Marche region, within the famous DOC of Verdicchio dei Castelli di Jesi, between the valleys of the river Esino and the Musone on one side, and between the Apennines and the sea on the other side. From the highest promontory of the Estate dominates the manor house, which houses the barrique, the family house, and an elegant Guest House.

Popular amenities for Cupo vacation rentals

  1. Airbnb
  2. Italy
  3. Marche
  4. Ancona
  5. Cupo