Condo holiday rentals in Guadalupe

4.95 out of 5 average rating, 538 reviews

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.

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.

4.94 out of 5 average rating, 105 reviews

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

A bright and airy living space is depicted, featuring a stylish side table and a decorative plant. A flat-screen TV is mounted on the wall, while a semi-open door reveals a glimpse of a bedroom. Light filters through floor-to-ceiling windows, enhancing the contemporary design.

4.94 out of 5 average rating, 387 reviews

Charming Apartment w A/C Near to the Int. Airport

Bienvenido a este encantador y elegante apartamento, en el piso 24; con una decoración exquisita Cuenta con dos cuartos, con camas de alta calidad: una Queen y otra matrimonial. Y un sofá cama en la sala 1 espacio de parqueo La cocina está completamente equipada. Disfruta de tus habilidades culinarias con tus seres queridos La torre cuenta con extraordinarias amenidades como piscina temperada, gimnasio y cuartos temáticos Aeropuerto: 16 km, aproximadamente 35 minutos, dependiendo del tráfico

4.94 out of 5 average rating, 354 reviews

Industrial 2BR perfect location w/AC + sunset view

Take a morning stroll in the park before heading back to your centrally-located, industrial 2 br apartment that will welcome you with high-speed wifi, top-of-the-line kitchen appliances, amazing decor, comfortable beds, and sunset views from a 12th floor overlooking the city. Not only will you have access to unparalleled amenities like a semi-Olympic pool, saunas, gym, and co-working space, you will be a walking distance from the best restaurants, coffee shops, and grocery stores in town.

A bright living space is illuminated by natural light coming through large windows, revealing a view of the city. A dining table with white chairs is positioned next to the windows. Colorful poufs and a wooden table add warmth to the modern decor.

4.85 out of 5 average rating, 926 reviews

Modern/comfort top floor apt perfect view Sabana

Enjoy a beautiful top-floor apartment with spectacular panoramic views of the city, which you can take in from the comfort of your private balcony. The apartment is ideally located just 400 meters from La Sabana Metropolitan Park, one of San José’s most popular green spaces, perfect for walking, jogging, relaxing, or simply enjoying the outdoors. ✈️ Juan Santamaría International Airport (SJO): approximately 10 miles (16 km) away, around 17 minutes by car in normal traffic conditions.

4.93 out of 5 average rating, 146 reviews

Condo 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.

An open studio layout is visible, featuring a dining table set for two, with blue plates and glassware. A comfortable sofa and a workspace with a chair are included. A neatly organized kitchen area is present, along with a glimpse of the bedroom area behind sliding doors.

4.88 out of 5 average rating, 286 reviews

Estudio c/ vista, balcón y parqueo gratis · URBN

Stay on the 12th floor of URBN Escalante, San José’s iconic tower, with city views from your private balcony. Enjoy a queen bed, a fully equipped kitchen, fast Wi-Fi, workspace, and FREE indoor parking. Located in the heart of Barrio Escalante, with 70+ restaurants, cafés, and bars within a 5-minute walk. Building amenities include a gym, heated pool, laundry room, coworking space, library, yoga room, cinema, and rooftop views. Check-in at the lobby is available 24/7

4.93 out of 5 average rating, 189 reviews

Loft Moderno con Vista Espectacular Escalante

Disfruta una estadía cómoda y acogedora en el corazón de Barrio Escalante, una de las zonas más vibrantes y gastronómicas de San José. Este moderno estudio ubicado frente al emblemático parque Francia totalmente equipado cuenta con una cama matrimonial, sofá cama matrimonial, baño completo, cocina funcional y un hermoso balcón privado con una espectacular vista a las montañas del sur de la ciudad, ideal para relajarse al amanecer o al final del día.

4.88 out of 5 average rating, 110 reviews

A well-lit sleeping area features a spacious bed dressed in crisp white linens, complemented by a blue throw blanket. Large windows provide a panoramic view of the surrounding landscape, while a small plant and two side tables accentuate the room. Soft curtains frame the window, enhancing the natural light.

Condo in Curridabat

Skyline Blue Apartment

Apartamento acogedor en uno de los mejores barrios de Curridabat, en este apartamento encontraras todo lo necesario para sentirte como en casa, tiene todos los servicios y comodidades necesarias. Aire acondicionado, parqueo gratuito, cocina equipada etc. Si necesitas algo adicional intentaremos conseguirtelo!! . El edificio cuenta con una gran cantidad de amenidades diseñadas para tu bienestar y comodidad. Piscina, coworking ,gimnasio entre otros.

4.97 out of 5 average rating, 102 reviews

A cozy bedroom features a spacious bed adorned with white linens and deep purple pillows. A window offers views of a vibrant garden, while a small seating area is equipped with a chair and table. Decorative elements include wall art and an elegant lamp.

Condo in Escazu

Escazú Haven #2· 2BR· Urban Cozy· A/C·WiFi·Parking

Enjoy your own space in Escazú, with the comfort of feeling at home. This cozy 2-bedroom apartment, each with A/C and a private en-suite bathroom, is ideal for couples, friends, or colleagues who want to share a place without giving up their personal space. This apartment combines quality amenities, warm wood finishes, and a private tropical patio with the convenience of city living—shops and restaurants are just a 2-minute walk away.

4.92 out of 5 average rating, 301 reviews

Oasis | URBN Escalante | A/C • Queen • Pool

Enjoy Barrio Escalante from a comfortable studio in URBN, equipped with air conditioning, a queen-size bed, sofa bed, fully equipped kitchen, and high-speed Wi-Fi. Ideal for couples, business travelers, or short stays in San José. You’ll have access to the swimming pool, gym, coworking space, and other building amenities, as well as restaurants, cafés, and supermarkets just a few minutes away on foot.

5.0 out of 5 average rating, 105 reviews

A bright living area features a comfortable sofa and a coffee table, with a large window offering a view of the vibrant greenery outside. Decorative artwork adorns the walls, and a potted plant adds a touch of nature indoor.

Condo in Uruca

River View Retreat · Pool · 20 min to Airport

Relax to the sound of the river and birdsong, with sweeping views of nature in the heart of San José. Aura is a modern apartment in a brand-new luxury residential tower — 20 minutes from the airport, walking distance to La Sabana Park (San José's central park), the National Stadium, and the Convention Center. Superhost · Guest Favorite · ★5.0 from 80+ stays.

Popular amenities for Guadalupe condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.89 out of 5 average rating, 118 reviews

Condo in Curridabat

Modern Loft in San José with Rooftop Pool

A modern kitchen area features a white island countertop with a stovetop, surrounded by sleek bar stools. A cozy living area with a gray sofa and decorative pillows is visible, alongside a window showcasing city views and palm plants adding a touch of greenery.

4.9 out of 5 average rating, 507 reviews

City view, A/C near the airport, 1903

A modern kitchen area features sleek cabinetry and stainless steel appliances, complemented by a dining space with stylish chairs. Large windows allow natural light to fill the room, providing a view of the greenery outside, creating a bright and open atmosphere.

4.95 out of 5 average rating, 175 reviews

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

4.84 out of 5 average rating, 225 reviews

A poolside area features two modern lounge chairs placed partially submerged in clear water, inviting relaxation. Surrounding the pool, several additional lounge chairs and a dining table can be seen. Potted plants add a touch of greenery to the space.

Condo in Curridabat

Perfect City Sunset Retreat 18th floor

A modern kitchen space features a central island with a variety of food options displayed. Greenery adorned with soft lights hangs from the ceiling, adding a touch of decor. In the background, a cozy seating area is visible next to large glass doors that open to a scenic view.

4.94 out of 5 average rating, 229 reviews

Joya Urbana en el piso 30; SECRT

4.89 out of 5 average rating, 244 reviews

A spacious bedroom features a king-size bed adorned with soft pillows and a cozy throw. Large windows provide a view of the mountains, while a mounted television is positioned on the wall. Light-colored artwork decorates the walls, enhancing the room's ambiance.

Condo in San José

Magical Penthouse in Prime Location+ Cima Hospital

A contemporary kitchen area is visible, featuring a kitchen island with a stovetop. Shelves display glassware and decorative items. A cozy seating area is placed nearby, complemented by natural light filtering through sheer curtains. Greenery is suspended from the ceiling, adding a fresh touch.

4.95 out of 5 average rating, 193 reviews

Modern Cozy Apartment, Amazing Amenities

4.84 out of 5 average rating, 111 reviews

Amazing Apart SECRT Sabana/ AC+Gym+Swimming pool

Pet-friendly condo rentals

The image captures a serene pool area surrounded by lush greenery, offering views of the city skyline and distant mountains. Bright blue skies provide a natural backdrop, while two green chairs are positioned nearby for relaxation.

4.92 out of 5 average rating, 233 reviews

9.9 mill SJO | Pool View | Cozy Loft | Parking

4.93 out of 5 average rating, 322 reviews

A well-lit interior space features large glass doors and vibrant wall art in bold colors, enhancing the modern aesthetic. Two wooden tables are positioned against the walls, complemented by wooden stools. Lush greenery is visible through the open doors, creating a seamless connection to the outdoors.

Condo in Alajuela

CozyApartment 10 Min fromJSM Airport+Parking+wifi

4.97 out of 5 average rating, 150 reviews

A living area features a large flat-screen TV mounted on a deep green wall. A soft gray sofa is positioned in front of a low coffee table with decor items. A tall plant adds greenery, and a glass door invites natural light from outside.

Condo in Desamparados

Casa Verde · 7 min from SJO · Pool+Gym · Fast WiFi

4.95 out of 5 average rating, 315 reviews

A serene pool area is showcased, featuring clear blue water surrounded by a smooth concrete deck. Lush greenery and potted plants enhance the space, while several lounge chairs are positioned nearby, inviting relaxation under the sun.

Condo in Alajuela

5 min from Airport | Transfer ($) | Pool | Gym

A bright kitchen area features a colorful wall adorned with abstract shapes and fruit motifs. A set of four wooden stools is positioned at a white counter, while a teal sofa adds a pop of color to the space.

4.88 out of 5 average rating, 120 reviews

Ponderosa Flat

A living area is furnished with a pink and white patterned loveseat and a matching armchair. A glass coffee table is positioned at the center, reflecting natural light from the large glass doors that open to a lush exterior view.

4.83 out of 5 average rating, 371 reviews

Alicia's Garden Apartment at Secrt

A modern high-rise building is presented, showcasing a unique façade with numerous windows. The structure stands tall against a cloudy sky, with city views and mountains visible in the background, emphasizing its elevated location in the urban landscape.

4.83 out of 5 average rating, 164 reviews

Único Apartamento en Nuevo y Moderno Condominio

4.86 out of 5 average rating, 626 reviews

Condo in Heredia

Cozy&secure apt Stunning views 15 min from airport

Condo rentals with a pool

An outdoor terrace is illuminated softly by wall fixtures, offering a vantage point over a sprawling cityscape at night. A seating area with two chairs and a small table can be seen, surrounded by greenery, creating a serene and inviting space.

4.91 out of 5 average rating, 159 reviews

Stylish 1 BR w A/C, Private Terrace

4.94 out of 5 average rating, 108 reviews

Sky Garden 1905 | Rooftop Pool • Gym • Cowork

A vibrant succulent plant sits atop a table, set against a backdrop of a city skyline illuminated at night. The distant lights of buildings and streets form a sparkling mosaic beneath a dark sky, offering a serene and inviting view.

4.77 out of 5 average rating, 185 reviews

Urbn Escalante Downtown View

A panoramic view captures the vibrant hues of sunset illuminating the sky, set against the backdrop of La Sabana Park. The iconic architecture of the Costa Rica National Stadium is visible, while the cityscape showcases a mix of modern buildings and green spaces.

4.96 out of 5 average rating, 219 reviews

Luxury & Comfy Apartment in San Jose, 30th floor.

A modern light fixture with a geometric design is showcased above a textured table. The background features a vibrant mural with colorful patterns and graffiti elements, adding visual interest to the dining space.

4.93 out of 5 average rating, 190 reviews

SanJoseito, Luxury in the City

A rooftop pool area is displayed, featuring several lounge chairs in vibrant teal. The pool is framed by planters with greenery, with a backdrop of modern buildings and mountains in the distance. The setting is illuminated by clear blue skies.

4.84 out of 5 average rating, 126 reviews

Cozy Studio w A/C perfect to Home Office or Relax

A sleek lap pool is surrounded by lush greenery and tropical plants, providing a serene atmosphere. The pool features a stone border and is set against a wooden deck. Steps lead down to the pool area, with a panoramic view of the surroundings.

4.85 out of 5 average rating, 175 reviews

Fully equipped apartment in Nunciatura

A curved swimming pool features clear blue water, surrounded by lush greenery and modern buildings. Several blue lounge chairs are positioned near the pool, creating a serene atmosphere. Floor-to-ceiling windows of the adjacent building reflect natural light and contribute to the inviting outdoor space.