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Holiday houses in San Cassiano

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Top-rated holiday rentals in San Cassiano

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Guest favourite
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

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.

4.94 out of 5 average rating, 18 reviews
Top Guest favourite
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

"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.

4.86 out of 5 average rating, 22 reviews
Guest favourite
Villa in San Cassiano

{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.

5.0 out of 5 average rating, 13 reviews
Top Guest favourite
A staircase leads down to a light-filled living space, featuring large glass doors that open to a sea view. The area is styled with comfortable seating and decorative pillows, while a small table and folding chairs are positioned outside on the terrace.
Home in Santa Cesarea Terme

Elegant Seafront House, Direct Access - Salento

Sea-view retreat with direct access in the authentic heart of Salento. Welcome to Cas’almare 9.7, where time slows and the sea becomes part of everyday life. This elegant two-level home is thoughtfully designed and ideal for couples and families. The highlight? Direct access to the sea and its waterfront terrace. Just steps from the natural thermal baths of Santa Cesarea and close to Otranto and Castro, it’s perfect for exploring the coast, with crystal-clear waters and local flavors.

4.98 out of 5 average rating, 49 reviews
Top Guest favourite
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

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.

5.0 out of 5 average rating, 36 reviews
Top Guest favourite
A relaxing outdoor area features a deluxe hot tub surrounded by lush greenery and a spacious garden. Comfortable seating arrangements can be seen nearby, offering a peaceful environment for guests to unwind under the trees.
Villa in Nociglia

Villa Giulia w/hot tub - Artemisia Homes

Imagine a manor house in the heart of Salento, an oasis of elegance and comfort nestled in a charming village just ten kilometers from the sea. This splendid residence, surrounded by a lush Mediterranean garden, offers a unique experience that combines the charm of tradition with contemporary luxury. The house has four large bedrooms, each with its own unique style. The soft-colored walls, granite floors and star vaults create a warm and welcoming atmosphere.

4.97 out of 5 average rating, 29 reviews
Guest favourite
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

The ecotourist's home.

The Ecotourist 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.

4.92 out of 5 average rating, 146 reviews
Guest favourite
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.
Holiday home in Tricase

La Salentina, sea, nature & relaxation

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.

4.93 out of 5 average rating, 410 reviews
Guest favourite
A serene pool area showcases a modern design with wooden decking and a crystal-clear swimming pool. Lush Mediterranean greenery surrounds the space, with comfortable seating under a parasol and expansive views of the sea, inviting relaxation and enjoyment of the outdoor setting.
Villa in Marina di Marittima

Wp Relais Villa Marittima

Villa Marittima, located in a protected area, overlooks the sea just 10 meters away along the coast of lower Salento. The villa, nestled in a protected area, offers a breathtaking view that, on days of great clarity, allows you to glimpse the mountains of Albania. Located 2 km from Castro, 7 km from Tricase Porto and a short distance from the picturesque Acqua Viva cove, the villa offers a unique experience between nature and comfort.

4.93 out of 5 average rating, 56 reviews
Guest favourite
The outdoor area features a private pool set against a panoramic view of the sea. Sun loungers are arranged along the poolside, surrounded by olive trees and Mediterranean vegetation, creating a peaceful atmosphere. The sky above displays a mix of clouds and blue, enhancing the scenic backdrop.
Villa in Marina Serra

SalentoSeaLovers Dream Trulli Villa Sea View

Villa Teresina is a dreaming home holidays with a breathtaking view of the sea. we are SalentoSeaLovers - direct owners of holidays homes all by the sea and unforgettable genuine and local experiences. Choose one of our homes for a perfect holidays! Villa has 6 beds, 3 baths, grounds with outdoor kitchen, big BBQ, sun beds, sofa, table and chairs for outdoor dining and also a rocking chair!

4.92 out of 5 average rating, 37 reviews
Top Guest favourite
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

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

5.0 out of 5 average rating, 48 reviews
Top Guest favourite
Home in Castro

Casa Le Radici – Castro

Welcome to "Le Radici" home! Located on the enchanting coasts of Salento, our home welcomes you with the warmth and authenticity of tradition. Immersed among centuries-old olive trees and with panoramic views of the sea, enjoy a unique experience, surrounded by nature and Salento culture. Take a break from the daily grind.

4.92 out of 5 average rating, 64 reviews

Popular amenities for San Cassiano holiday rentals