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Vacation rentals in San Cassiano

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Top-rated vacation rentals in San Cassiano

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

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A villa sits gracefully on a hillside, overlooking the expansive sea. The structure features a circular design, surrounded by greenery and shaded areas. A pool is visible in the backyard, enhancing the outdoor space. The landscape showcases a mix of natural terrain and manicured gardens.
Villa in Andrano
4.81 out of 5 average rating, 72 reviews

"Li Saccuddi - Villetta Belvedere"

This villa offers a breathtaking panorama. The house is located in an exceptionally picturesque location on a small plateau about a kilometre from the sea in Marina di Andrano. The accommodation was decorated with careful attention to detail and is very neat and tidy. Stone tubs, the restored antique bed, woven straw baskets, evoke the rural, rustic life and craftsmanship of the Salento region. The old wrought-iron bell for calling the family to the table is also a particularly charming feature.

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
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
4.98 out of 5 average rating, 47 reviews

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.

Guest favorite
A spacious living area features two light-colored sofas adorned with blue patterned cushions, arranged around a round wooden coffee table. A modern fireplace is positioned against a stone wall, and natural light filters through sheer curtains, enhancing the room's welcoming ambiance.
Vacation home in Botrugno
5.0 out of 5 average rating, 12 reviews

LA PIGNA BLU-CasaVacanza con Piscina-13km dal mare

La nostra casa vacanza è una struttura pensata per accogliere turisti o persone che desiderano trascorrere un periodo di relax e riposo lontano dalla propria abitazione.Ogni dettaglio è stato curato con attenzione, offrendo un atmosfera accogliente e confortevole. La cucina è completamente attrezzata con utensili ed elettrodomestici. Zona pranzo molto spaziosa Le camere da letto sono ampie con letti comodi. Giardino e piscina condiviso ideale per rilassarsi e per preparare un barbecue

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 pochi km dalle più famose località adriatiche Otranto e Castro Marina. M&G suite è una tipica casa salentina arredata con stile. Le tre camere da letto e relativi bagni danno la possibilità di ospitare famiglie numerose o gruppi di amici che vogliono condividere un indimenticabile vacanza nel Salento senza rinunciare alla loro privacy. Un ampio spazio esterno esclusivo con piscina e docce esterne, porticato con tavolo e sedute esterne. Parcheggio privato interno alla proprietà.

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 a Relais L'Oliveto con piscina e wifi

L'Oliveto, è una giovane e fresca masseria pugliese con piscina e wifi, dotata di 6 appartamenti con angolo cottura, bagno privato ed aria condizionata. Appartamento "il Fico", è dotato di area relax ed è Ideale per giovani famiglie o coppie, ogni proprietà, può ospitare fino a 4 persone. Al centro della costa adriatica, ed a pochi km da Castro, è posizione ideale per chi vuole visitare l'intera costa. Anche mete come Otranto, Santa Cesarea o Leuca, sono facilmente raggiungibili.

Top guest favorite
A charming outdoor space is framed by tall trees, featuring a stone pathway and seating area with dark wicker chairs. Colorful flower pots accent the scene, while the tranquil blue of the sea is glimpsed in the background, enhancing the serene environment.
Home in Marina di Marittima
4.98 out of 5 average rating, 111 reviews

Sulla Caletta dell'Acquaviva a 20 metri dal mare.

The house "Perla dell 'Acquaviva" , in the middle of the Otranto-Leuca natural park , offers an enviable private access to the sea and the privilege of entering the waters of the cove through a comfortable rocky staircase different from the other bathers. The property consists of bathroom, bedroom, kitchen-living room, porch overlooking the sea. You will be welcomed by large outdoor spaces with a relaxation area among tall trees and the relaxing roar of the waves.

Top 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, 408 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
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

La casa dell’ecoturista.

La Casa dell’Ecoturista è un antico riparo agricolo recuperato in bioarchitettura. È una piccola casa-isola offgrid, autosufficiente dal punto di vista energetico, isolata nella campagna salentina. Si trova nell’Uliveto Pubblico del Parco Paduli, luogo simbolo e museo a cielo aperto. È parte di un progetto culturale vivo. Se vuoi rallentare e vivere un luogo carico di senso e diverso dal turismo convenzionale, è il posto giusto per te.

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 - "Antica Liama salentina"

‘‘Pajara Marinaia’’ sorge sulla scogliera a sud di Castro in prossimità della Cala dell'Acquaviva. L'antica liama salentina, fronte mare, si compone di una camera da letto matrimoniale, una cucina attrezzata con tutti i comfort, un grande bagno, una ampia terrazza con pergolato e piscina privata, a sfioro, vista mare. La casa dispone inoltre di un accesso privato al mare, la cui discesa risulta agevole grazie a scalette in pietra

Guest favorite
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
4.93 out of 5 average rating, 56 reviews

Wp Relais Villa Marittima

Villa Marittima, situata in una zona protetta, si affaccia a soli 10 metri dal mare lungo la costa del basso Salento. La villa immersa in una zona protetta, offre una vista mozzafiato che, nei giorni di grande nitidezza, permette di intravedere le montagne dell'Albania. Situata a 2 km da Castro, 7 km da Tricase Porto e a breve distanza dalla suggestiva cala dell'Acqua Viva, la villa offre un'esperienza unica tra natura e comfort.

Popular amenities for San Cassiano vacation rentals