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Holiday rentals in San Cassiano

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Top-rated holiday rentals in San Cassiano

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Guest favourite
A room with warm-toned walls features a large wooden table surrounded by vibrant, patterned rugs. An intricately designed cabinet stands against the wall, showcasing decorative glassware. Soft lighting is provided by wall sconces, and historical wooden doors create an inviting atmosphere.
Villa in Vitigliano
4.98 out of 5 average rating, 46 reviews

Relais Porta D'Oriente

You will love the Casa del Tabacco because it is a charming and full of comfort Historical Residence placed in a strategic area of the Salento. One of the most beatiful Italian coasts is less than 5 km away, in 22 minutes you can join Otranto, in 36 minutes Lecce. Your stay will be beatiful and special because, as experienced travellers, the owners will propose you authentic restaurants, wine and food tasting, cultural and naturalistic tours, scuba diving, massages, experiences for the youth.

Top guest favourite
A serene pool area is shown, featuring a private heated pool with clear water. Sun loungers are arranged nearby, and a shaded cabana offers a comfortable retreat. Lush greenery surrounds the space, enhancing the tranquil outdoor setting.
Villa in Spongano
4.95 out of 5 average rating, 147 reviews

Villa Ada Independent villa - heated private pool

Rural house, pajara, just renovated in the countryside, inside a 10thousand mq olive tree grove with abreath-taking panorama. Nicely furnished,full equipped with air condition, a big outside private pool with hydromassage ( 3.5x11 m) and kitchen area with accessories. The pool is independent, heated all day and night ( 24-28 degrees) and just for the house, the only structure situated in the villa. The wifi is very good also for working inside the house. Only 5km far from famous turist sea-side

Guest favourite
The living area features a vaulted stone ceiling, lending a rustic charm. A comfortable sofa with decorative cushions sits beneath warm lighting from two lamps. An antique wooden cabinet is positioned against the wall, complemented by two wooden chairs.
Home in Tricase Porto
5 out of 5 average rating, 16 reviews

Il Mandorlo - Rural luxury in the middle of nature

Upon arrival, you will find a house away from everything but in contact with the most precious thing we have: the nature of Salento. Il Mandorlo is one of the five houses available at Agricola Le Cupole and is the most suitable for couples of friends or families who want to immerse themselves in an experience in contact with the authenticity of the territory. The comfortable size of the house and the typical atmosphere of the pajare, contribute to creating an intimate and inspiring place.

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
5 out of 5 average rating, 28 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.

Top guest favourite
A sunlit terrace features two wooden lounge chairs, positioned to overlook the expansive ocean. The stone railing is adorned with several potted plants, complementing the serene coastal view under a clear blue sky.
Home in Tricase Porto
5 out of 5 average rating, 38 reviews

Tricase Porto, beautiful with access to the sea

Vintage Salento-style apartment, recently renovated with great taste and all comforts. An outdoor space that can be used and a priceless private descent to the sea that makes bathing in coves and natural pools dug into the rocks exclusive and solitary, even on the busiest days of the summer! The apartment is part of a complex overlooking the sea that has a large condominium garden, a reserved space where you can eat under the stars and overlooking the sea and use the barbecue

Top guest favourite
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
4.99 out of 5 average rating, 96 reviews

On Caletta dell'Acquaviva, 20 meters from the sea.

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 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
4.93 out of 5 average rating, 383 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 favourite
A glimpse of the inviting plunge pool is framed by a light-toned patio. The large glass doors lead into a cozy dining area featuring a wooden table and chairs. Lush greenery decorates the outdoor space, enhancing the serene atmosphere.
Home in Depressa
5 out of 5 average rating, 13 reviews

Casa Micocci by Casa Camilla Journey

Welcome to Casa Micocci, a design focused retreat in the heart of Depressa, Tricase. Best for groups of three or four - a family of four with two small children, or three adults travelling together - the house features a king-size bed with linen sheets and a 3.5-meter-long custom sofa. The full kitchen, private plunge pool, and thoughtfully designed interiors make every detail a joy. Every element is locally made, celebrating Salento’s craftsmanship.

Top guest favourite
An enchanting view of the coastline is visible at dusk from the spacious covered terrace. Soft light from decorative lanterns casts a gentle glow, enhancing the atmosphere. The sea and the town below can be seen in the distance, framed by curved architectural elements.
Flat in Castro
4.96 out of 5 average rating, 71 reviews

Terrace with sea view

The apartment enjoys tranquility and privacy and an enchanting panoramic view of the sea and the coast of Salento, accessible from a large terrace. Its location is ideal for walking to the sea and the ancient city. The apartment, finely renovated, has a spacious covered terrace, with attention to every detail, to enjoy outdoors, both during the day and during the evening hours, the beautiful scenery of the city's cove and the Salento coast.

Guest favourite
An outdoor space is depicted, featuring whitewashed walls and terracotta accents. A wooden door, framed by potted plants, leads to a passageway. A tall palm tree and rooftops of nearby buildings create a quaint backdrop, characteristic of the local architectural style.
Home in Matino
4.95 out of 5 average rating, 101 reviews

house in Ca'mascìa courtyard

Un posto dove il tempo scorre lento, dove hai voglia di non fare niente! La casa è situata nel cuore del centro storico di Matino, a ridosso del Palazzo Marchesale, a pochi passi da Piazza S. Giorgio e dalla chiesa. E' ideale per trascorrere le vostre vacanze in assoluta tranquillità, godendo di un'atmosfera di altri tempi pur stando a pochi minuti da Gallipoli e dalle bellissime spiagge del Salento.

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
5 out of 5 average rating, 29 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

Guest favourite
A dining table is adorned with a green glass vase filled with dried grasses, complemented by four wine glasses filled with red wine. Fresh produce and a round loaf of bread are presented on a wooden board, with a softly lit bedroom visible in the background.
Home in Spongano
5 out of 5 average rating, 16 reviews

Small residence in Salento

Cosy home recently renovated by the owners, and open for short term stays. It is fully equipped with linen and towels and the basic provisions. The house offers a spacious kitchen, one bedroom (note the bed size is approx 145 cm x 190 cm) and served by a small toilet, a living room with sofa and TV, and the main bathroom with shower. The patio is of exclusive use.

Popular amenities for San Cassiano holiday rentals

  1. Airbnb
  2. Italy
  3. Apulia
  4. Lecce
  5. San Cassiano