Family-friendly holiday rentals in Guadalupe

4.95 out of 5 average rating, 534 reviews

A rooftop jacuzzi is positioned against a stunning sunset backdrop. It is surrounded by clear glass panels, offering a panoramic view of the city. The deck is made of dark wood, enhancing the tranquil outdoor space.

Apartment in Escalante

Quiet Gorgeous Queen Bed Studio Apartment+Jacuzzi

Extremely safe doorman building located in one of the 50 coolest neighborhoods in the world according to the time out magazine. Best Location in town !!! Be received by staff who will enable an ease check-in with a smart lock into the apartment. Enjoy the view of an amazing sunset in the jacuzzi, then get ready to dine in one of the 70 restaurants in the area. Afterwards, come back to sleep in an extremely comfortable queen bed. Wake up and make an exquisite cup of gourmet costarican coffee.

4.95 out of 5 average rating, 136 reviews

An aerial view showcases a charming house surrounded by lush greenery and rolling hills. The property features a curved pathway leading to the home, set against a backdrop of dramatic clouds and distant mountain views, highlighting the tranquil privacy of the location.

Home in Guadalupe

Amazing view of San Jose (20 min)- Casa los Cielos

Casa Los Cielos is elegant but rustic, with beautiful Costa Rican woodwork throughout. Rooms all have stunning views including the San Jose valley and surrounding mountains. It is nestled in a cool (78F), peaceful mountainous area, is perfect for families, retreats, or groups of friends. Enjoy the chimney, fire pit, BBQ grill and horses in neigboring lot.Pets are welcome! - 20 min from downtown San Jose - 50 min drive to Int'l airport - 1h 45m from beach - 5 min drive to restaurants, stores

A bright sitting area features wooden seating against the walls, complemented by a small step ladder leading to an upper space. Large windows allow natural light to fill the room, while a glimpse of the outdoor balcony and greenery can be seen through the open door.

4.88 out of 5 average rating, 272 reviews

Cosy & Modern MiniHouse • Cerca UCR • Seguro

Este es un espacio moderno que ofrece todas las comodidades, muy bien iluminado y acogedor. Totalmente equipado y privado. Además está en un residencial tranquilo, con muchas zonas verdes, privado y seguro, parqueo bajo techo. Traslado rápido a comercios, 5 minutos de la Universidad de Costa Rica, 15 minutos del centro de San Jose y restaurantes. Muchas zonas verdes alrededor. Cocina equipada, buena señal WiFi, suficiente para teletrabajo. Agua caliente, Smart TV con Netflix, YouTube y otros.

4.96 out of 5 average rating, 202 reviews

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.

4.91 out of 5 average rating, 422 reviews

A spacious bedroom features a wooden bed against a backdrop of large windows, providing a panoramic view of the urban landscape below. The room is equipped with light-colored bed linens and a nearby white cabinet, enhancing the minimalist design.

Loft in Curridabat

Studio con hermosa vista/ Amazing View Studio

Ubicado en el piso 23 de torre iFreses en Curridabat, cuenta con vista a la zona Sur de San José. Dentro del estudio encontrá todo lo necesario para su estadía, podrá hacer uso de las amenidades del condominio como la piscina y iwork. Located on the 23rd floor of iFreses tower in Curridabat, with great view of the south of San José city. Inside, you will have all that you need. You could use some of the amenities of the condo like pool and iwork. Check-in 3:00pm and Check-out 11:00am.

A large outdoor swimming pool is surrounded by a sunlit deck, featuring lounge chairs positioned along one side. The modern high-rise building stands in the background, with expansive glass windows reflecting the blue sky and sunlight.

4.89 out of 5 average rating, 511 reviews

Best location, cozy Apartment!

Beautiful condo in perfectly located apartment building. The whole place has a modern feel to it without losing a touch of home. The unit is composed of one bedroom with an ensuite bathroom, living room and deck to relax and enjoy the views, as well as a modern kitchen and laundry machine. This cozy and modern apartment is close to all the best restaurants and night life in San Jose, as well as museums and downtown. Major public transportation is right outside the door.

4.85 out of 5 average rating, 164 reviews

A two-story building features large windows and a covered outdoor area, creating a welcoming entrance to Casa Burío. In the foreground, a classic vehicle is visible alongside a horse in a lush green space, while the sky displays soft hues of sunset.

Cabin in Heredia

Burio house, beautiful cabin, coffee and nature

A perfect getaway 25 minutes from San Jose on the hills of San Rafael de Heredia. Casa Burio is a fully equipped loft surrounded by coffee fields. Live an authentic coffee experience, enjoy the view of the central valley from our viewpoint, walk among the coffee plantations, and learn about coffee with our tour. Also, you can appreciate our beautiful horses or savor a delicious typical breakfast at an extra charge. It is a magical place to celebrate life and nature.

The living-dining area features a light-colored sofa with decorative pillows, set against a textured wall. A dining table with chairs is positioned nearby, while a window allows for a glimpse of the common patio outside. Neutral tones and tiled flooring provide a calm ambiance.

4.8 out of 5 average rating, 359 reviews

La Vecindá - The Studio - Great Location

NO PARKING AVAILABLE / NO HAY PARQUEO🚫🚙 A small apartment in the heart of San José, in a traditional "Vecindad" type complex: several apartments around common internal patios, due to this there’s a high Humidity in this space. The best location: in the middle of the most culturally active neighborhoods of San José (Amón, Otoya, Escalante, San Jose, La California), with the main theaters, museums, galleries, plazas, gastronomy, nightlife, shows and much more.

4.84 out of 5 average rating, 116 reviews

Loft in San Pedro

Estudio céntrico en San Pedro | 200+ reseñas

Estudio céntrico en San Pedro, con excelente valoración y más de 200 reseñas de huéspedes. Ideal para moverte caminando y disfrutar San José con facilidad. Espacio cómodo, seguro y totalmente equipado, perfecto para estancias cortas o largas. Ubicación estratégica cerca de la UCR, restaurantes, supermercados y transporte público. Ideal para viajeros solos o parejas. Alojamiento con amplia experiencia y excelentes valoraciones de huéspedes.

4.88 out of 5 average rating, 125 reviews

A bright, open kitchen and dining area features a round table with four chairs and a modern light fixture above. A cozy green sofa is positioned beside a large window with arched detailing, while a black refrigerator stands against the wall, complementing the minimalist design.

Flat in Escalante

Oasis Ecalante Apartamento 2H 1B

¡Descubre el encanto de Barrio Escalante desde nuestro acogedor apartamento de 2 habitaciones! La habitación principal te ofrece cama queen, escritorio y TV. La segunda habitación cuenta con una cama individual y escritorio. Adicional cuenta con un baño cómodo. Disfruta de espacios amplios en la sala, comedor y cocina totalmente equipada. Ubicado estratégicamente, estarás rodeado de cafés, restaurantes y la vibrante vida nocturna.

A bedroom features a spacious bed with a patterned quilt, flanked by a nightstand and a lamp. A piece of wall art depicting a serene landscape hangs above the bed. Natural light filters in through a window, contributing to the cozy ambiance.

4.78 out of 5 average rating, 117 reviews

Casa Flamboyán - Cómoda, segura y céntrica.

Cómodo apartamento para 4 personas con una habitación y un área social con sofá cama matrimonial en un lugar seguro, céntrico y con fácil acceso a los servicios públicos. Totalmente equipado con cocina completa, lavadora y secadora de ropa; con baño completo, agua caliente, TV por cable, WiFi gratis y 1 estacionamiento. Ubicación en zona segura, cerca de atracciones turísticas, hospitales, farmacia, supermercados y bancos.

4.83 out of 5 average rating, 228 reviews

A simple living area features a sleek gray sofa adorned with decorative cushions in various colors. A small white table with a mirror is positioned in front, accompanied by a potted plant. Natural light filters through sheer curtains on a nearby window.

Flat in San Pedro

Tropical Escape

El apartamento se encuentra completamente equipado con todas las amenidades de entretenimiento, cocina y lavado para ser su segundo hogar en la ciudad. Es un lugar seguro, espacioso, elegante y muy céntrico perfecto para escapar del bullicioso y acelerado ritmo citadino y transportarse a la pacífica esencia tropical de Costa Rica. IMPORTANTE: Este es un condominio de ambiente FAMILIAR y TRANQUILO. MULTA DE $50 por ruido.

Popular amenities for Guadalupe family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.85 out of 5 average rating, 323 reviews

An outdoor terrace features dark wood flooring surrounded by tropical plants. Two lounge chairs are positioned near a hot tub, offering panoramic views of the cityscape and mountains in the distance, creating an inviting space for relaxation.

Loft in Escalante

Peacful studio apt. near the hip Barrio Escalante

4.93 out of 5 average rating, 140 reviews

Apartment in Sabana

La Madriguera Serena/ SECRT Sabana.

4.87 out of 5 average rating, 409 reviews

A spacious studio features a cozy sleeping area with a full bed, complemented by modern built-in shelving. A small dining table with four chairs sits near a large window, offering stunning city views, while a comfortable couch completes the inviting layout.

Loft in Escalante

Brand new 1 bed loft with spectacular city view

4.86 out of 5 average rating, 616 reviews

The unique architecture of the loft is showcased with an angled facade and large glass windows that reflect the surrounding greenery. A small deck area features modern outdoor seating, inviting relaxation amidst the natural landscape.

Villa in San Roque

Nebulae Loft · Design Stay with Jacuzzi & Firepit

4.92 out of 5 average rating, 205 reviews

An exterior view of the villa is captured at night, showcasing a well-lit pathway lined with potted plants. The building features arched windows and a covered porch, while the moon illuminates the sky, enhancing the tranquil ambiance.

Villa in Belen

Georgeus Villa, pool, additional jacuzzi, A/C

4.97 out of 5 average rating, 117 reviews

Home in Alajuela

Luxury Retreat Near SJO – Nature, Comfort & Style

4.94 out of 5 average rating, 352 reviews

Apartment in Rohrmoser

Industrial 2BR perfect location w/AC + sunset view

4.88 out of 5 average rating, 137 reviews

A rectangular pool with shimmering blue tiles is surrounded by a stone deck. A water slide extends from a raised platform to the pool. Lush palm trees and a small grassy area are featured alongside the pool, providing a relaxing outdoor space.

Home in Alajuela

Luxury in your Home, private Pool and Jacuzzi.

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 753 reviews

An open living area features exposed brick walls and a sleek staircase leading to the upper level. A yellow door adds a pop of color, while a table with chairs and a comfortable seating area are visible. Light enters through a window, enhancing the spacious feel.

Loft in San Bosco

Lovely one bedroom loft with a nice comfy patio.

4.98 out of 5 average rating, 350 reviews

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

Guest house in San Rafael

A rustic cottage is surrounded by a lush garden with vibrant green grass. The building features a white exterior accented by blue details and includes wooden doors and windows. A picnic table is positioned nearby, shaded by trees.

4.95 out of 5 average rating, 236 reviews

La Casita Rústica, naturaleza, aves y mariposas.

4.86 out of 5 average rating, 635 reviews

A stunning view of a sunset over the city skyline is captured, with vibrant orange and yellow hues blending into the sky. The horizon features silhouettes of distant mountains, while glass railings enclose a rooftop pool setting, reflecting the warm colors of dusk.

Loft in Curridabat

Amazing View at 20th SJO Floor Loft! Parking&Pool

Home in Concepción de San Isidro

A lookout platform features a tiled floor and wooden steps, overlooking a vast landscape. Panoramic views of mountains are visible under a serene sky, with mist rolling through the valleys below. Lush greenery surrounds the area, enhancing the natural beauty.

4.82 out of 5 average rating, 407 reviews

Boutique Working Coffee Ranch 3

Shipping container in Barva

4.95 out of 5 average rating, 188 reviews

Dream Homes Vacaciones Heredia-8.5 miles Airport

4.8 out of 5 average rating, 281 reviews

A cozy bedroom features a spacious bed adorned with neutral-toned linens. Natural light filters through large glass windows, framed by rich red curtains. A unique wooden shelf hangs on the wall, adding artistic interest to the room.

Flat in Zapote

Apt#11 Modern 1 BR w/SofaBed for extra 2 guest

4.98 out of 5 average rating, 168 reviews

Flat in San Rafael

Apart. Relajante 2 k Univ.obsicori Heredia San Raf

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 143 reviews

A modern living space is showcased with a sleek gray sofa facing a wall-mounted television. A minimalist dining area with two chairs is positioned near large windows offering expansive views of the cityscape and mountains. The concrete walls provide a contemporary ambiance.

Flat in Curridabat

Vivi's Hideaway

4.94 out of 5 average rating, 154 reviews

Loft in Curridabat

Loft con balcón vista panorámica y parqueo privado

4.96 out of 5 average rating, 142 reviews

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

4.87 out of 5 average rating, 108 reviews

Flat in Escalante

Apt BoEscalante/Free Parking compact car/City view

4.95 out of 5 average rating, 196 reviews

A modern living area includes a plush sofa facing a small table and chair. Bright lighting is provided by recessed ceiling fixtures. The walls are painted in a neutral tone, complemented by a minimalistic artwork. Large glass doors lead to a balcony, allowing natural light to fill the space.

Apartment in Escalante

Modern apartment at gastronomic epicenter

Holiday home in Escalante

A panoramic view captures the San Jose skyline at sunset, showcasing a blend of city lights and natural hues across the horizon. The silhouette of mountains can be discerned, complementing the vibrant oranges and purples of the evening sky.

4.91 out of 5 average rating, 244 reviews

URBN Barrio Escalante Fully Equipped 20th Floor

4.94 out of 5 average rating, 171 reviews

A spacious bed with neutral-toned bedding is positioned near large glass windows, offering a nighttime city view filled with twinkling lights. Soft curtains frame the windows, complementing the warm color palette of decorative pillows arranged on the bed.

Home in Curridabat

Smart loft en el corazón de la Ciudad A/C y wifi