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Vacation rentals in San Cassiano

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Top-rated vacation rentals in San Cassiano

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Guest favorite
A shaded seating area is situated beside a serene pool, featuring four white lounge chairs and a small table. Elegant sheer curtains flow gently in the breeze, offering a relaxing space among the surrounding olive trees.
Loft in Surano
4.94 out of 5 average rating, 18 reviews

Casa il Fico in Relais L'Oliveto with pool and wifi

L'Oliveto is a young and fresh Apulian farmhouse with swimming pool and Wi-Fi, equipped with 6 apartments with kitchenette, private bathroom and air conditioning. The "il Fico" apartment is equipped with a relaxation area and is ideal for young families or couples. Each property can accommodate up to 4 people. At the center of the Adriatic coast, and a few km from Castro, it is an ideal location for those who want to visit the entire coast. Destinations such as Otranto, Santa Cesarea or Leuca are also easily accessible.

Top guest favorite
A serene swimming pool is framed by lush green grass and bordered by stone pavers. Relaxing lounge chairs are set under umbrellas, inviting guests to unwind. The clear water reflects the sky, enhancing the tranquil atmosphere of the outdoor space.
Villa in Surano
4.86 out of 5 average rating, 21 reviews

"Borgogelso", a beautiful oasis in Salento.

A courtyard house in Salento booked out entirely (only July and August) for you and your group of friends. A beautiful oasis where you can experience the perfect combination of culture, the sea, good food and exclusive facilities. Four living spaces designed for you and your friends. Four variations on the same theme: relaxation. Here, the use of restored traditional materials meets modern, minimalist interior design and the comfort of cutting-edge facilities in a fresh and natural environment.

Guest favorite
Villa in San Cassiano
5.0 out of 5 average rating, 13 reviews

{Salento - Elegance - Privacy}

Beautiful early 20th-century villa, carefully restored in the heart of Salento. Ideal for groups and families up to 10 guests, it offers 4 independent double bedrooms, each with a private bathroom and air conditioning, ensuring comfort and privacy. The property features a 400 sqm private garden and private parking. Located in peaceful San Cassiano, it is the perfect base to explore Otranto, Castro, Gallipoli, Santa Maria di Leuca and Lecce while enjoying authentic Salento away from the crowds.

Top guest favorite
An outdoor area features a swimming pool surrounded by lounge chairs and umbrellas for shade. A stone wall provides privacy, and a pergola with outdoor seating can be seen in the background under clear blue skies.
Home in Poggiardo
5.0 out of 5 average rating, 35 reviews

M&G Suite Home

A few km from the most famous Adriatic resorts of Otranto and Castro Marina. M&G suite is a typical Salento house furnished with style. The three bedrooms and their bathrooms offer the possibility of hosting large families or groups of friends who want to share an unforgettable vacation in Salento without sacrificing their privacy. A large exclusive outdoor space with swimming pool and outdoor showers, porch with outdoor table and seating. Private parking inside the property.

Top guest favorite
A crystal-clear swimming pool reflects the surrounding garden, which is filled with colorful flowers and greenery. The house features stone walls and a covered patio area adorned with curtains, offering shaded outdoor seating amidst a tranquil landscape.
Villa in Salve
4.97 out of 5 average rating, 63 reviews

Leukos, charming villa in Salento.

Independent villa and brand new in the Salento countryside. Surrounded by greenery in an enchanting view of centuries-old olive trees, it is just a 10-minute drive from the famous Maldives beach of Salento, also visible from the elevated terrace. Its strategic location allows you to visit the most famous Salento resorts such as Gallipoli, Otranto, Leuca and choose a beach on the Ionian or Adriatic. The interiors are stylishly furnished, combining refinement and functionality.

Guest favorite
A serene outdoor space is highlighted, featuring a rectangular swimming pool bordered by well-maintained grass. Lounge chairs are positioned along the poolside, and the structure's rustic architecture is complemented by greenery. Bright blue skies provide a vibrant backdrop to the scene.
Villa in Specchia Gallone
5.0 out of 5 average rating, 19 reviews

Villa Sofia - Tradition and modernity in Salento

Thanks to the careful renovation work, the ancient Palmento, an authentic place in the agricultural tradition of Salento, has been transformed into a welcoming and relaxing place where the original elements such as the pools, the ancient fireplaces, and the star vaults dialogue perfectly with contemporary design and oriental furnishings. The large rooms overlooking the garden and swimming pool, all independent, guarantee privacy and absolute tranquillity for all guests.

Guest favorite
The eco-friendly house is situated amidst lush greenery, featuring a unique architectural design with stone elements. Large windows allow ample daylight into the interior. A spacious outdoor area is surrounded by olive trees, providing a serene atmosphere for relaxation.
Home in San Cassiano
4.92 out of 5 average rating, 146 reviews

The ecotourist's home.

The Ecotourist's House is an ancient agricultural shelter recovered in bio-architecture. It is a small, off-grid, energy self-sufficient island house, isolated in the Salento countryside. It is located in the Public Olive Grove of the Paduli Park, a symbolic place and open-air museum. It is part of a living cultural project. If you want to slow down and experience a place full of meaning and different from conventional tourism, this is the right place for you.

Home in San Cassiano
5.0 out of 5 average rating, 4 reviews

House in Salento

Located inland, our house offers a convenient starting point for visiting Salento, from Lecce to the most renowned and well-known seaside resorts such as Castro, Santa Cesarea, Otranto, Gallipoli, Maldive del Salento, and Santa Maria di Leuca. The home is located on the ground floor with a separate entrance from the garden. It offers a full bedroom, an extra bed, an equipped kitchen, and a bathroom. Small pets are allowed at the property with prior notice.

Guest favorite
An outdoor area features a hot tub with bubbling water and soft lighting. A wooden deck showcases an elegant seating area with white furniture and blue cushions. Steps lead up to the main house, where dining space is visible under a pergola, surrounded by greenery and tall trees.
Vacation home in Tricase
4.93 out of 5 average rating, 407 reviews

La Salentina, sea, nature & relax

Nestled in Mediterranean nature and overlooking a spectacular crystal-clear sea, La Salentina is a welcoming home in the deep south of Puglia, along the scenic Otranto–Santa Maria di Leuca coastal road. With two sea-view terraces, thoughtfully designed interiors and a hydromassage tub with chromotherapy, it’s the perfect retreat for those seeking relaxation, authenticity and beauty a place where each day begins with the magic of the sunrise over the sea.

Guest favorite
Villa in Diso
4.95 out of 5 average rating, 43 reviews

Wp Relais Locanda Fiore di Zagara

La Locanda Fiori di Zagara è una dimora storica del 1700 situata nel cuore di Diso, un incantevole paese del Salento a soli 3 km dal mare. La residenza WP Relais è stata sottoposta a un attento restauro conservativo, preservando i colori, i materiali e il design originali.Questo intervento ha permesso di riportare in vita il fascino del passato, integrandolo con un alto livello di comfort.

Guest favorite
Villa in Diso
4.83 out of 5 average rating, 6 reviews

villa[2 suites] 5 minute from sea| A/C |garden

🏡 2 Apartments in a villa with garden 🌞🏖️🌊 Strategic location: Just a few minutes from Castro, Santa Cesarea Terme, Otranto, and the stunning coves of the Salento Adriatic coast. ❄️ Total comfort: Air conditioning in both apartments. 👫 Ideal for: Families, couples, or small groups of friends looking to experience an authentic Salento vacation while enjoying both peace and comfort.

Top guest favorite
A private infinity pool is featured, with clear blue water seamlessly blending into the horizon. The surrounding stone terrace offers unobstructed sea views, while a railing provides safety and access from the pool to the adjoining areas.
Trullo in Marina di Marittima
5.0 out of 5 average rating, 45 reviews

Pajara Marinaia - "Old Salento Liama"

''Pajara Marinaia'' is located on the cliff south of Castro near Cala dell'Acquaviva. The ancient Salento liama, facing the sea, consists of a double bedroom, a kitchen equipped with all amenities, a large bathroom, a large terrace with pergola and private infinity pool, with sea view. The house also has private access to the sea, the descent of which is easy thanks to stone stairs

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