Family-friendly holiday rentals in Cinco Esquinas

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cinco Esquinas

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

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Guest favourite

An inviting outdoor area features a private heated pool surrounded by tropical plants and potted flowers. Comfortable seating options, including a hammock and lounge chairs, are positioned around the pool, with a cozy dining area visible in the background under soft lighting.

Villa in Mata Redonda

Cheerful private 4-Bedroom Villa. Heated pool A/C

For a group or a cozy couple, this bright and spacious home delivers comfort and style. Located in a quiet, modern, and safe neighborhood, you’re just minutes away from downtown. Great restaurants are close by and a block away from new Microsoft tower. 4 bedrooms (A/C), sleeps up to 9 , 3 full bathrooms & private heated pool. Fully equipped modern kitchen, stocked with staples and more. Starts at $195 per night for up to 4 guests, $35 per extra guest. Cleaning included. Come dive into city life.

4.96 out of 5 average rating, 142 reviews

Top guest favourite

A spacious rooftop area is presented with stylish seating arrangements, including a sectional sofa and a coffee table. The view overlooks the city skyline and surrounding landscape, with warm light from the setting sun adding a serene ambiance.

Apartment in Mata Redonda

Scenic, 3BR Condo | Pool, Gym & 24/7 Security

Located at walking distance from Sabana Park, this modern retreat offers the perfect blend of city energy and private peace in the heart of San Jose - High speed Internet (fiber) - Blackout curtains and quality beds to recharge. - Nice restaurants across street - Stunning rooftop gardens with 360 views - 3 Bedrooms with 3beds + Sofa bed - 2 TVs with digital channels. - Kitchen ready to cook anything. - Balcony - Laundry area with washing machine available - Air Conditioning - 2 car parking

4.94 out of 5 average rating, 102 reviews

Guest favourite

A modern house with a sleek black facade is set against a twilight sky. Warm light emanates from its windows, contrasting with the cool evening hues. Lush green grass surrounds the structure, enhancing its harmonious connection to nature.

Farm stay

Mountain farm retreat near San Jose

Escape to a modern mountain farmhouse near San José, designed for families who crave more than a stay. Wake to sweeping views of green valleys, ocean, and mountains from wide windows. Collect fresh eggs, meet friendly farm animals, wander gardens and 300+ trees, then gather around the fire pit for wood-fired pizza under the stars. Black facade, exposed concrete, warm wood from the Osa Peninsula. Sleeps 6, self check-in, fully fenced yard. Slow down, reconnect, and create memories that last.

4.96 out of 5 average rating, 200 reviews

Top guest favourite

The kitchen features modern appliances, including a black refrigerator and built-in oven. A small island with sleek stools offers additional seating. A plant adds a touch of greenery, while the light countertops contrast with the dark cabinetry, creating an inviting cooking space.

Apartment in Mata Redonda

Top Pick in La Sabana: Comfy & Spotless, San José

Luxury apartment, spotlessly clean, with high-speed Wi-Fi, 24/7 security, free parking, self check-in, AC, in-unit washer and dryer, blackout curtains for a restful night’s sleep, Smart TV, and a fully equipped kitchen. Strategically located just 25 minutes from Juan Santamaría International Airport, with easy access to downtown San José, La Sabana, and the National Stadium. 8 restaurants, cafés, a supermarket, and a vibrant dining district are conveniently located just across the street.

4.95 out of 5 average rating, 173 reviews

Top guest favourite

A spacious living area features a plush blue sofa with yellow accent pillows. Large sliding glass doors provide a panoramic view of the valley below, leading to a furnished terrace. Natural light enhances the modern design, complemented by indoor plants and wooden accents.

Home in Escazu

KING BED, deluxe stay, @HillView, green areas, A/C

Enjoy this king-bed deluxe apartment, you will find everything needed for an enjoyable stay. It is situated in a prime location yet you will feel away from the city. Close to malls, restaurants, tours, etc. You will be impressed by every beautiful detail handcrafted by Giulio, a passionate architect who loves to create harmonious and inviting spaces. The apartment is bright and cozy, with large windows that let in natural light and offer a breathtaking view of the city and the countryside.

4.98 out of 5 average rating, 348 reviews

Top guest favourite

Apartment in Sabana

La Madriguera Serena/ SECRT Sabana.

La Madriguera Serena se encuentra en el corazón de San José, a pocos minutos de La Sabana, el pulmón verde de la ciudad. Su ubicación es ideal tanto para viajeros de negocios como para quienes desean explorar la capital con comodidad. Rodeado de cafeterías, restaurantes, supermercados y servicios, podrás moverte fácilmente a pie o en transporte. Estarás cerca de centros corporativos, zonas médicas, estadios y principales vías de acceso, sin renunciar a un ambiente tranquilo y seguro.

4.93 out of 5 average rating, 138 reviews

Top guest favourite

A modern living area features a comfortable sofa adorned with a cozy throw blanket. A decorative butterfly display is set on a textured side table, complemented by framed art of natural scenes and a floor plant. Soft lighting from a stylish lamp enhances the inviting atmosphere.

Flat in Uruca

Airport Apt/floor16 AC+Paking+Rooftop views +Tours

Relax into a unique Japandi-style experience in a new, luxurious tower. The stylish decor, full kitchen, and a dedicated desk with high-speed internet provide a perfect blend of comfort and productivity for any traveler. Enjoy stunning sunrises, sunsets, and night views from your own private space, adding a touch of luxury and relaxation to your stay. Enjoy a pool, rooftop lounges, a cinema, a gym, co-working spaces, and an on-site food court, offering a complete vacation experience.

4.99 out of 5 average rating, 162 reviews

Guest favourite

A studio space features a queen/twin bunk bed with soft linens and a spacious layout. A kitchenette with a mini-fridge and microwave is visible. Natural light illuminates the room, complemented by modern fixtures and a ceiling fan. The tiled floor adds to the clean, contemporary look.

Holiday home in San José

2Bed/1Bath Apartment with Patio in San Jose Center

Located in San Jose Downtown. A large queen/twin bunk bed sleeps 3 guests comfortably along with a private bathroom with hot water shower. The apartment features Air Conditioning, a private Kitchen with a mini-fridge, microwave, and sink, LCD TV with cable, and fast WIFI Internet. There is a work area with a desk and two stools. The Outdoor Patio features natural light and a sitting area. The apartment is on the Second Floor Building, reception area has a night Security Guard.

4.85 out of 5 average rating, 295 reviews

Guest favourite

An aerial view of the 67m2 duplex suite is displayed, showcasing a layout that includes two bedrooms, a living area, and a kitchen. The arrangement highlights spacious interiors and designated areas for both relaxation and dining.

Flat in Mata Redonda

#5 full bufet diario cortesía 2 hab. / 1 baño

Ofrecemos servicio de recepción abierta 24/7 para hacer su llegada más fácil WI FI DE 50 MEGAS SIMETRICOS. , desayuno todos los días (lunes a viernes de 6:30 a.m. a 9:00 a.m. & sábados y domingos de 7a.m. a 10:00 a.m. A/C en dormitorios . Icluye el 13% de impuesto de venta, sala de reuniones, piscina, estacionamiento externo e interno (limitado a disponibilidad), acceso al restaurante L'Olivo Y una instalación de lavandería que funciona con monedas en el área común.

4.79 out of 5 average rating, 217 reviews

Guest favourite

The kitchen and dining area features modern appliances and a spacious layout. Black countertops are complemented by white cabinetry. A wooden dining table with four chairs is present, along with a small island equipped with bar stools. Natural light enters through large windows adorned with yellow curtains.

Flat in San José

Casa361-Paseo Colón-NEAR EVERYTHING-New-EQUIPPED-2

NEW Apartment #2, COMPLETE, PRIVATE and independent for up to 7 people with two bedrooms and a social area with a sofa bed, fully equipped with a full bathroom, equipped kitchen, laundry, parking (write to me before booking I need to know the size of your car.), Wi-Fi, safe and cable With the most convenient location for your stay in a safe area near tourist attractions, embassies, hospitals, government offices, and main bus terminals to tourist areas of the country

4.83 out of 5 average rating, 721 reviews

Superhost

A spacious living and dining area is presented, featuring a round table with four chairs and a comfortable grey sofa facing a wall-mounted TV. Light-colored cabinetry and appliances complement the modern décor, while an assortment of framed photos adds a personal touch.

Apartment in San José

Fully-Eq. 2BR 2BA in Luxury GC w/Pool+Gym+24/7Sec

Welcome to Apartment 406, your stylish 786ft² (73m²) sanctuary in Costa Rica—the largest unit in the Bambú Rivera Residential Complex! Perfect for digital nomads and vacationers, this modern 2-bedroom apartment is fully equipped for a comfortable stay. With 24/7 security and a wealth of amenities, you're just a short distance from the city center and its attractions. Whether you're here to work, explore, or unwind, this is the ideal home base for your trip.

4.9 out of 5 average rating, 116 reviews

Guest favourite

A modern dining area features a sleek glass table surrounded by dark upholstered chairs. Elegant table settings with neutral plates and decorative gold accents create a polished look. In the background, a spacious living area is visible, showcasing comfortable seating and artistic wall decor.

Flat in Amón

Arona’s#5 Boutique 3Bedroom unit+free gated garage

Elegant and modern apartment, down town San José (1240 Sq feet Size). Great and safe location. Accessible to many places, walking distance to restaurants, stores, pubs, supermarket, etc. There’s a guide map to help you to find places to go! High Speed Internet (200 MGB) Apt is fully equipped. Hot water. 2 Rooms with Queen Size bed each, and 1 twin bed for 1 person to sleep in Room # 3. Living room has another Sleep Coach, also has a TV, with cable.

4.94 out of 5 average rating, 361 reviews