Family-friendly holiday rentals in Casarano

Masseria Gemini, a XVIII century luxury retreat

Elegant Masseria with Pool, Private Cinema, Panoramic Terrace & Wellness beside the Maldives of Salento Summer stays are precious, July and August weeks are often reserved long in advance. Set between the historic town of Ugento and Salento’s breathtaking beaches, Masseria Gemini is an 18th-century estate exquisitely restored to blend contemporary luxury with timeless Apulian charm. Every space invites serenity, privacy, and indulgence, offering an unforgettable escape of wellbeing and elegance.

Indoor spaces · Family · Checkout

SEA FRONT, Casa Allegria Santa Maria al Bagno Sea

Recently renovated seafront apartment with breathtaking sea views and romantic sunsets. Located between two charming coastal villages linked by a beautiful seaside walk, in one of the most sought-after areas of Salento. Cafés, restaurants, beach, local market are all within short walking distance. A scenic coastal road runs between the house and the sea, offering easy access to the waterfront. Perfect for guests who want to explore Salento while waking up to a sea view. Free private parking.

Family · Kitchen · Quiet

Authenticity, charm and typicality!

In the heart of the historic center of Matino, a delightful house with a panoramic terrace from which to enjoy the most beautiful sunsets in Salento. The flagship of the property is undoubtedly the panoramic terrace: a corner of paradise suspended on the roofs of the town, from which you can admire one of the most spectacular sunsets in Salento. When the sun descends behind the hills, the sky is tinged with red, orange and gold, giving a different show every evening.

Kitchen · Indoor spaces · Amenities

Historic Palazzo with courtyard and plunge pool

Contemporary spaces within a historic residence with a courtyard, just a few minutes from Ionian beaches such as Punta della Suina or Lido Pizzo. 🍹The property features a private Plunge Pool located on the rooftop terrace (a 6 sqm, 80 cm deep relaxation pool) for your exclusive use. 🔊 Please note: One of the three bedrooms faces the street. Since the apartment is on the first floor, some traffic noise can be expected at times. The other two bedrooms are quieter.

Indoor spaces · Comfort · Quiet

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.

Family · Kitchen · Long stay

Villa Le Ozze

A magical place featuring a large swimming pool and three fully independent accommodation options around it, providing a total of 11/12 beds. The swimming pool has a sand filter system and a robot for more thorough cleaning. Nearby, under the tiled roof, you can enjoy your BBQs in comfort at the barbecue area, which has a table for 12 people. And that’s not all – there’s also a sound system that you can connect to your mobile phone via Bluetooth.

Family · Kitchen · Beach

VILLA with heated pool Torre San Giovanni

🌿 Trullo TerraNostra is a beautiful modern villa immersed in the peace of an olive grove in Ugento/Torre San Giovanni. With a private pool, playground, tree house, ping pong table, pet friendly, it can accommodate up to 17 people. Just a few minutes from the white-sand beaches of Salento, it's perfect for those seeking relaxation, nature and comfort, with ample space for families and friends and unforgettable moments of togetherness and fun.

Kitchen · Family · Quiet

U Palazzu de Tuie - Valentina's Houses

U Palazzu di Tuie is an elegant historic residence located in the heart of Tuglie, a charming village just a few minutes from Gallipoli, where traditional architecture meets contemporary comfort. The result of a careful and recent restoration, the palace has been brought back to its former splendor with great respect for the original structure. Its authenticity has been preserved while seamlessly incorporating every modern convenience.

Kitchen · Indoor spaces · View

vaults under the stars - 13 km from the sea

Typical Salento construction with star vaults, spacious and bright in an excellent location for visiting the most beautiful beaches and villages of Salento. The property has two large bedrooms with private bathrooms; the first is located on the ground floor, the second on the first floor with access from an external staircase. Guests will have a beautiful living area, equipped kitchen, laundry and terrace at their disposal.

Family · Kitchen · Condition

house in Ca'mascìa courtyard

A place where time passes slowly, where you feel like doing nothing! The house is located in the heart of Matino’s historic centre, close to Palazzo Marchesale and just a short walk from Piazza S. Giorgio and the church. It is the perfect place to spend your holidays in complete tranquillity, enjoying an old-world atmosphere while still being just a few minutes from Gallipoli and the beautiful beaches of Salento.

Kitchen · Indoor spaces · Condition

Pousada Salentina

Pousada Salentina is an authentic refuge in the heart of Matino, where Salento elegance meets the warmth of Brazilian art. A quiet and refined house, ideal for those seeking relaxation and authenticity. An intimate and relaxing place where time slows down between the quiet of the village and a beautiful plunge pool on the terrace. In just ten minutes you will reach the beautiful beaches of Salento.

Indoor spaces · Kitchen · Amenities

The little olive trees

A small apartment in the countryside at the gates of Casarano, surrounded by flowering plants and nestled in a quiet olive grove. 15 km from Gallipoli and 20 from the Maldives of Salento, it is a convenient base for exploring beaches, cliffs and villages in South Salento, but it is also the ideal place to stay to relax and enjoy the tranquility of the countryside in the shadow of a thick jasmine.

Kitchen · Indoor spaces · Cleanliness