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Family-friendly holiday rentals in Casamassella

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Casamassella

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Superhost
A serene swimming pool is framed by vibrant greenery, featuring clear blue water that reflects the sky. A stone wall and a door are visible in the background, adding structure to the tranquil setting.
Villa in Giurdignano
4.85 out of 5 average rating, 55 reviews

Designer Villa with Pool 10 minutes from Otranto

It is a beautiful villa in the center of Giurdignano, just a 10-minute drive from Otranto. The house is a 5-minute walk from the main square and restaurants, supermarkets and shops. The courtyard has a beautiful designer pool (1.20 and 2.10m deep) and the house is modern, furnished with designer pieces and works of art and is spread across two floors. The two floors, the 5 rooms are large and comfortable and new bathrooms. A large table inside and one outside will allow guests to choose where to eat.

Top guest favourite
A spacious bedroom features a large window with views of the outside. Light-colored walls and wooden beams enrich the room's character. A patterned bedspread covers the bed, complemented by a decorative lamp and an ornate dresser that add functional elegance to the space.
Home in Otranto
5 out of 5 average rating, 43 reviews

Historical Home - Historical Home in Otranto

Goditi una vacanza all'insegna dello stile in questo spazio in centro. Il Palazzo era sede del Consolato Veneziano sulla Via della Seta. Venezia, per ordine del Consiglio dei Dogi, mandò a Otranto una loro nobile famiglia che diventò il punto referente, a livello burocratico e amministrativo, per tutto il traffico delle navi che da Venezia andavano in Oriente e viceversa. Il Palazzo è stato recentemente oggetto di un restauro conservativo che lo ha riportato fedelmente al suo stato originario.

Top guest favourite
Home in Lecce

Oasi Gorgoni Charming House & Pool

Lussuoso e confortevole appartamento, a ridosso del centro della città, ideale per godersi il relax, la città e il mare. Dotato di ogni comfort (3 camere, 3 bagni, living, piscina privata, giardino, Wi-Fi, aria condizionata, lavatrice, biancheria, stoviglie, parcheggio privato), l’appartamento è situato in uno dei quartieri più tranquilli e sicuri di Lecce. A soli 10 min. dal mare, consente di raggiungere facilmente sia la costa costa adriatica (Otranto), che la costa ionica (Gallipoli).

Guest favourite
An outdoor dining area features a large table surrounded by colorful chairs under a bamboo pergola. Spacious glass doors invite natural light from the modern kitchen inside, while lush greenery forms the backdrop, enhancing the tranquil setting for al fresco dining.
Flat in Uggiano La Chiesa
4.93 out of 5 average rating, 30 reviews

[ Cima Apartment ] - Masseria La Lazzara

MODERN ideal location for RELAXING stays created by the famous architect Umberto Riva surrounded by GREEN a few steps from OTRANTO LARGE and BRIGHT OPEN SPACE living room and RELAXATION area MODERN equipped kitchen TWO SPACIOUS bedrooms with direct access to a well-kept GARDEN Flowered PERGOLA with OUTDOOR table to spend pleasant moments of conviviality STRATEGIC POSITION just a few minutes from OTRANTO offers FREE COVERED PARKING ON SITE Free WIFI AIR CONDITIONED apartment

Top guest favourite
Villa in Tricase
5 out of 5 average rating, 64 reviews

La Dimora – Historic residence with private terrace and sea view

“May all who enter as guests, leave as friends ” Historic villa ON the sea IN A PRIVATE PARK WITH panoramic private TERRACE. The Villa has a double room, a nice room with a second double bed accessible by a small staircase, a bathroom and a living room with a well-equipped kitchen, a large and magnificent sea view terrace with large porch and tastefully furnished. The house has a private parking lot and is located inside a large villa with a park that goes all the way to the sea.

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, 98 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.

Guest favourite
A serene pool area is surrounded by lush greenery and flowering plants. A sunshade covers a seating area next to the inviting turquoise water, with lounge chairs available for relaxation. Olive trees and other Mediterranean flora enhance the tranquil garden setting.
Home in Parabita
4.93 out of 5 average rating, 116 reviews

Ulivi al tramonto: country home with private pool

‘Ulivi al tramonto’ is located just a few minutes from Gallipoli. Surrounded by greenery and the scents of Salento, this detached house has a large garden, private parking, Wi-Fi and exclusive use of the swimming pool. An ideal starting point for visiting Salento. Nestled on the hill behind the Gulf of Gallipoli, it allows you to relax after a day at the beach or spent visiting the beautiful towns of Salento. Perfectly furnished apartment with exclusive pieces.

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, 389 reviews

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.

Guest favourite
A spacious pool area is highlighted by a large pink flamingo float. The property features a white-walled house under a clear blue sky, with shaded outdoor seating nearby. Lush greenery surrounds the pool, enhancing the tranquil outdoor setting.
Villa in Specchia
4.94 out of 5 average rating, 53 reviews

Casa La Porticina

In the heart Salento, Casa La Porticina is located short drives from the rocky Adriatic coast, sandy Ionian beaches, and near so many discoveries in between. 1.5 miles from the historic center of Specchia, with choices of restaurants, bars and evening festivals throughout the year. Specchia continues to land on travel sites’ must see villages of Salento. https://magazine.dooid.it/en/uncategorized/visit-specchia-salento/ INSTAGRAM: @casalaporticina

Superhost
An outdoor open space features a shaded gazebo supported by a wooden structure. Several black chairs surround a table, and two lounge chairs are positioned nearby. Lush green plants and a white wall offer privacy while enhancing the serene ambiance.
Tiny home in Casamassella
4.81 out of 5 average rating, 109 reviews

Vicolo 19

Bright studio located in an alley of a small village three km from Otranto, equipped with air conditioning, TV, mini fridge, iron, hairdryer, towels and soap. The kitchen is located outside, shared with another room; it is well-equipped with the essentials for cooking. Coffee and sugar are also available. Attached open space with gazebo, tables, chairs, and deck chairs. Located next door, another studio for those traveling with friends.

Top 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, 106 reviews

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 center, close to Palazzo Marchesale and just a short walk from Piazza S. Giorgio and the church. It is the perfect place to spend your vacation in complete tranquility, enjoying an old-world atmosphere while still being just a few minutes from Gallipoli and the beautiful beaches of Salento.

Top guest favourite
The kitchen features a combination of light cabinetry and wood accents, equipped with modern appliances. A spacious dining table with six white chairs is positioned in the center. Decorative dishware and potted plants add a touch of charm to the functional design.
Home in Casamassella
4.93 out of 5 average rating, 56 reviews

The "Back"

Just five minutes from Otranto, a charming newly restored house in which an atmosphere like that of the old houses of Salento has been recreated, combining modern comforts with a style of yesteryear. The house is equipped with a washing machine, dishwasher, air conditioning, iron, wifi, safe, hairdryer, outdoor barbecue, second bathroom, and outdoor shower with hot water.

Popular amenities for Casamassella family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Casamassella

  • Total holiday rentals

    Explore 20 holiday rentals in Casamassella

  • Nightly prices starting at

    Casamassella holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 380 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Casamassella holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Casamassella rentals

  • 4.8 Average rating

    Casamassella stays are highly rated by guests – averaging 4.8 out of 5!

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