Family-friendly holiday rentals in Guadalupe

4.95 out of 5 average rating, 526 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.

Condo 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.

4.87 out of 5 average rating, 408 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

Keep it simple at this peaceful and centrally-located place. Experience the exclusivity of this modern studio in Barrio Escalante, with an unbeatable location just minutes from downtown San Jose, 30 minutes from Tobias Bolaños airport. Enjoy your stay surrounded by smart amenities and beautiful views of the city, complete with Wi-Fi connection, a full-size bed, private bathroom, kitchen and access to superior conveniences, such as a rooftop with jacuzzi and deck, lounge room, gym and BBQ area.

4.98 out of 5 average rating, 341 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

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.

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.

4.91 out of 5 average rating, 414 reviews

Studio with a beautiful view/ Amazing View Studio

Located on the 23rd floor of Torre iFreses in Curridabat, it overlooks the South area of 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 studio space features a queen bed positioned beside large windows with mountain views. A modern area with a television and a small dining table is visible. Green accent walls complement wooden furnishings. Natural light illuminates the room, creating a bright and airy atmosphere.

4.97 out of 5 average rating, 135 reviews

Original Studio - San José -Barrio Escalante A/C

Enjoy the simplicity of this quiet and central accommodation in the heart of Barrio Escalante, one of the most exclusive places in the city of San José where you will find a wide range of cuisine, private hospitals, dental clinics, and beauty salons. Our Studio will offer you everything you need to have a more than pleasant stay. If we're talking about shopping malls, you'll find Multiplaza del Este and Mall San Pedro the closest where you'll find everything! See you soon!✌️

An outdoor infinity pool offers scenic views of the surrounding mountains and cityscape. Several lounge chairs are positioned along the poolside, while a smooth, tiled deck extends for relaxation. The tranquil water reflects the overcast sky, providing a serene atmosphere.

4.86 out of 5 average rating, 467 reviews

Modern studio with spectacular view and amenities

Good and easy access location near supermarkets, malls, night life centers, near a Main Street on Curridabat and near a train station. Spectacular amenities such as coworking space, gym, tempered pool and other common areas, as well as friendly staff in the building. The apartment is equipped with crockery and basic kitchen utensils and the bathroom is provided with soap, shampoo and conditioner. There is a private WiFi, a smart tv and A/C. There is one bed an one sofa bed.

Superhost

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, 356 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.

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, 270 reviews

Cozy & Modern MiniHouse • Cerca UCR • Seguro

This is a modern space that offers all the comforts, very well lit and cozy. Fully equipped and private. It is also in a quiet residential, with many green areas, private and safe, indoor parking. Quick transfer to shops, 5 minutes from the University of Costa Rica, 15 minutes from downtown San Jose and restaurants. Lots of green area around. Equipped kitchen, good WiFi signal, enough for teleworking. Hot water, Smart TV with Netflix, YouTube and more.

4.95 out of 5 average rating, 199 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

Magical Mountain family Farm Experience

Heavenly Highlands is a modern mountain farm retreat near San José, created for families who want more than just a stay. Enjoy peaceful views, friendly farm animals, fresh eggs, gardens, fruit trees, a cozy fire pit, and unforgettable experiences like wood-fired pizza. With beautiful architecture, local craftsmanship, and nature all around, it’s the perfect place to slow down, reconnect, and create memories your family will truly remember.

4.87 out of 5 average rating, 397 reviews

10th floor Apartment w/ Sky-Level Pool in San José

Private, comfortable, and strategically located in the heart of Curridabat. This studio on the 10th floor of the iFreses building is perfect for couples, students, or travelers seeking a quiet and functional space. It offers all the essentials for a pleasant stay and is surrounded by universities, shopping centers, and restaurants. Its location makes it a strategic base to explore San José and plan your journey through Costa Rica.

Superhost

Loft in San Pedro

4.84 out of 5 average rating, 113 reviews

Central studio in San Pedro | 200+ reviews

Centrally located studio in San Pedro, with an excellent rating and over 200 guest reviews. Ideal for getting around on foot and enjoying San José with ease. Comfortable, safe, and fully equipped space, perfect for short or long stays. Convenient location close to the UCR, restaurants, supermarkets, and public transportation. Ideal for solo travelers or couples. Host with extensive experience and excellent guest reviews.

4.91 out of 5 average rating, 144 reviews

The sleeping area features a spacious bed covered with a light-colored quilt. A wall-mounted TV is positioned across from the bed, with a window providing ventilation and a glimpse to the outside. Neutral tones create a calming environment.

Apartment in San Pedro

Cozy Private Apartment 5 Min Walk to UCR

Your home away from home in San Pedro, a 5-min walk to UCR. Cozy private apartment for up to 2 guests, with full bed, private bathroom with hot shower, kitchenette, fast WiFi, and fresh linens and towels. Shared main entrance to the property, quiet inside. No on-site parking; easy access on foot, by bus, or rideshare. Surrounded by cafés, restaurants, and supermarkets, with quick transport to San José.

Popular amenities for Guadalupe family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 179 reviews

A dome-shaped structure sits nestled in a lush, green landscape. Rolling hills are visible in the background, covered in dense vegetation. The surrounding area is open and inviting, creating a serene natural setting.

Dome in Piedades

“Magical dome in the heights”

4.92 out of 5 average rating, 123 reviews

Condo in Sabana

The Madriguera Serena/ SECRT Sabana.

A cozy sleeping area features a spacious bed dressed in crisp white linens with an orange accent blanket. Natural light floods in through large glass doors leading to a private balcony, where two chairs provide city views. A simple rug adds warmth to the floor.

4.98 out of 5 average rating, 152 reviews

Spacious studio with balcony

4.92 out of 5 average rating, 118 reviews

Lucy's Studio - Escalante Neighborhood

4.86 out of 5 average rating, 614 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

4.88 out of 5 average rating, 135 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.

4.96 out of 5 average rating, 113 reviews

Home in Alajuela

Luxury Retreat Near SJO – Nature, Comfort & Style

A modern bedroom is illuminated by city lights through large windows. A spacious bed with crisp white linens is positioned beside a wall-mounted smart TV. A cozy seating area with a gray armchair and a round table is included, creating a welcoming space for relaxation.

4.92 out of 5 average rating, 102 reviews

Modern Apt- trendy Escalante CR

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 131 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

4.88 out of 5 average rating, 173 reviews

The living area features a cozy couch with decorative cushions beside a wooden table. A modern floor lamp provides soft lighting. The kitchen area includes essential appliances, such as a stove and microwave, with storage space below. A potted plant adds greenery to the room.

Apartment in San Pedro

Spacious Apartment in Great Location

4.94 out of 5 average rating, 737 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.

A modern studio apartment features a combined living and dining area with a glass table and upholstered chairs. Natural light enters through large windows, offering views of the surrounding landscape. A wooden screen separates the sleeping space, which contains a spacious bed dressed in neutral colors.

4.94 out of 5 average rating, 185 reviews

Escalante Bellevie Apartment

4.93 out of 5 average rating, 174 reviews

Condo in Escalante

Modern Loft with a Spectacular View of Escalante

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.

4.86 out of 5 average rating, 628 reviews

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

4.89 out of 5 average rating, 302 reviews

BeST RANkED SuPERHOST * 18th Floor * KInG sIZE BeD

4.96 out of 5 average rating, 635 reviews

The master bedroom features a spacious bed adorned with soft linens and decorative pillows. A cozy chair sits beside a shelf with potted plants, while double glass doors open to an outdoor patio surrounded by lush greenery.

Home in Alajuela

Tropical Oasis 5 min to SJO airport W/ cozy deck

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 140 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.

Apartment in Curridabat

Vivi's Hideaway

4.93 out of 5 average rating, 192 reviews

A spacious living area showcases a comfortable bed with blue accent pillows, facing a kitchenette with modern appliances. A dining table is positioned nearby alongside blue chairs. White shelving units provide storage, while a patterned chair adds a touch of style to the room.

Apartment in Curridabat

Ifreses Apartment: clean/balcony/WiFi/desk

4.94 out of 5 average rating, 168 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 in the heart of the city, A/C and Wi-Fi

Apartment in Mata Redonda

A modern living area showcases a green sofa adorned with colorful cushions. Bright wall art featuring playful designs adds a lively touch. Large glass doors provide access to a balcony with expansive views, while a bedroom is visible through an open doorway, decorated with floral wallpaper.

4.94 out of 5 average rating, 470 reviews

Hideout in downtown San Jose-Sergio

4.94 out of 5 average rating, 778 reviews

A bright sleeping area features a spacious bed with quality linens and a cosy sofa bed. Large windows allow natural light to fill the room, while views of greenery are visible outside. Neutral walls enhance a calm atmosphere, complemented by simple decor elements.

Loft in Alajuela

Cosy Loft, 3 min from SJO airport, brand new

4.98 out of 5 average rating, 102 reviews

A modern studio is displayed with a cozy sleeping area featuring a spacious bed. A dining table is set with elegant glassware and decorative elements. Large windows allow natural light to brighten the room, complemented by soft curtains. A wall-mounted TV completes the inviting atmosphere.

Loft in Escalante

Apartment in Escalante Olive Loft 14th

A panoramic view of the city is showcased at dusk, with vibrant clouds illuminated by the setting sun. The skyline features a mix of tall buildings, while distant mountains rise in the background, providing a dramatic contrast against the colorful sky.