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Vacation rentals with a pool in Guadalupe

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Guadalupe

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
A spacious lounge area is featured with large windows, providing panoramic views of San José. Comfortable sofas are arranged around a central coffee table, and an artistic light fixture adds a touch of elegance. Subtle decor elements enhance the inviting space.
Apartment in Barrio Escalante
4.9 out of 5 average rating, 547 reviews

Stylish Studio with Sky Bar & City Views

New and exclusive Golden Coffee Studio, inspired by the history of Costa Rican coffee this apartment brings the best views of San Jose city. Walkable of the beaten heart of trendy gastronomic area Barrio Escalante, surrounded by the local vibes this place is on the best spot downtown for you to get ready and discover Costa Rica. One master room and a unique queen wallbed make this place an inviting and fun place for couples, friends and families. Spectacular amenities 100MBps Fiber optic Wifi

Guest favourite
Apartment in Curridabat
4.9 out of 5 average rating, 190 reviews

Studio at 24th floor - SJO view

Exclusivo apartamento en el Condominio iFreses piso 24, cerca del centro de San José, rodeado de tiendas, restaurantes, bares, barrios gastronómicos y más. Estacionamiento disponible por una tarifa adicional, no se permiten carros tipo pickup por tamaño/ Exclusive apartment at Condominio iFreses on the 24th floor, in the center of the city, surrounded by shops, restaurants, bars, gastronomic neighborhoods and much more. Parking available with an additional fee, no pickups are allow due to size.

Superhost
A cozy bedroom features a spacious bed adorned with a neutral-toned quilt and decorative pillows. A bedside table with a lamp stands beside the bed. Floor-to-ceiling windows offer views of the outdoor pool area and the surrounding landscape.
Loft in Francisco Peralta
4.89 out of 5 average rating, 123 reviews

Beautiful loft pool, gym and excellent location

Disfrute de una experiencia elegante en este lugar céntrico de San José, a poca distancia de los lugares más modernos, históricos y turísticos. Disfruta tranquilamente de un apartamento a estrenar con todo lo necesario para tu estancia. Tendrás un supermercado frente al edificio, pero también bares y restaurantes en Barrio Escalante. Acceso a excelentes amenidades: Gimnasio, 2 albercas, área de BBQ, firepit al aire libre, sala de cine, roof garden para disfrutar de vistas únicas de San José.

Top guest favourite
An infinity pool is seen on the rooftop, overlooking a city skyline at sunset. The water reflects the colors of the sky, while glass railings provide unobstructed views of the surrounding area and mountains in the distance.
Apartment in Urbanización Castro
4.96 out of 5 average rating, 139 reviews

Urban Modern Apartment - Roof Top Pool

Centrally located near La Sabana Metropolitan Park, my apartment offers a perfect blend of relaxation and functionality. The space is designed for comfort and it’s ideal for virtual work, with a fully equipped kitchen for energizing breakfasts or intimate dinners. Enjoy restful sleep, complete privacy, and the convenience of a full and half bathroom. The unique contemporary ambiance enhances your stay. Additionally, the apartment offers free parking within the building for added convenience.

Top guest favourite
A cozy bedroom is highlighted by a tufted headboard and plush bedding. Soft lighting is provided by two bedside lamps. Artwork featuring Alice in Wonderland decorates the wall above. A large window offers expansive views of the city and landscape beyond.
Apartment in Mata Redonda
4.97 out of 5 average rating, 139 reviews

Whimsical 27th Floor Apt, King Bed, AC, Parking

Victorian “Steampunk” Alice in Wonderland inspired apartment! Located on the 27th floor, our comfortable apartment boasts amazing views of the city. Originally a 2-bdrm floorplan, this unit was converted into a 1-bdrm, making it larger than most 1-bdrm units in SECRT Sabana. Safe building, central location, within walking distance to the National Stadium, La Sabana Park, restaurants, and supermarkets. SECRT Sabana is a funky building, famous for its fun Alice-themed common areas.

Guest favourite
The living and dining area of the apartment features a comfortable gray sofa adorned with decorative pillows. A sleek black dining table is surrounded by four light-colored chairs. Natural light floods the space through large glass doors leading to the balcony.
Apartment in Barrio Escalante
4.88 out of 5 average rating, 222 reviews

★Luxurious Apt★ | Panoramic View, Pool, Gym + Pkg

Relax at our luxury apt at a prime location from which you can easily experience all of San Jose. Marvel at the mesmerizing views from the 23rd floor of a modern, industrially designed building, in the heart of Barrio Escalante. Perfect blend of luxury comfort & convenience with a rich amenity list is there to satisfy your every need. • Fully Equipped Kitchen • Queen Bed • Flat-Screen TVs • Open Concept Design Living Area • Pool • Gym • Free Private Parking Learn more below!

Top guest favourite
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.
Condo in Barrio Escalante
4.9 out of 5 average rating, 137 reviews

Stylish 1 BR w A/C, Private Terrace

Enjoy a stylish experience at this centrally-located condominium, less than half a mile from downtown and in the heart of the trendy gastronomic Barrio Escalante with countless options of restaurants and bars. Whether working remotely, visiting friends, health tourism or on holiday, with speedy internet, fully equipped kitchen and bathroom, a very calm and serene terrace, gym and pool, coworking, lounge and bar, you will feel right at home with the touch of the latin culture.

Top guest favourite
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.
Condo in Mata Redonda
4.96 out of 5 average rating, 122 reviews

Urban Jewel on the 30th Floor; SECRT

Immerse yourself in the magic of this apartment on the 30th floor of SECRT Sabana, inspired by *Alice in the Wonderland*. Designed with warm floor and light decor, it has a private bedroom, closet, and working space. Fully equipped kitchen with essentials included, and bathroom with amenities. Enjoy spectacular views and buy snacks, drinks, and personal items available in the apartment. All you need for a unique and comfortable stay. Parking $15 additional

Guest favourite
A dining area features a glass table surrounded by four wooden chairs, elegantly placed beneath a decorative wall art piece. A cozy seating space includes a light-colored sofa, complemented by a decorative plant and ample natural light flowing through large glass doors that lead to a balcony with city views.
Apartment in Bella Vista
4.88 out of 5 average rating, 247 reviews

Gorgeous sunsets at charming apartment in downtown

We welcome you to your new and luxurious apartment in the center of the city, located in one of the most iconic residential buildings in the country, with a variety of amenities and just a 5-minute walk away from the most famous gastronomic area of ​​San José. The neighborhood is safe, and has different areas according to your preference (whether it's a night out, or a quiet afternoon in the park). A/C, WiFi 500 mbps, and parking included.

Guest favourite
A rooftop area features a heated pool with a reflective surface, surrounded by modern lounge chairs. The skyline of the city is visible in the background, contrasting against twilight clouds, while a group of people can be seen enjoying the view.
Apartment in San Pedro
4.93 out of 5 average rating, 246 reviews

Couples Focused Magnificent Studio Apartment

FREE early check-in upon request!! Escape stress in our stunning 23rd-floor adult-only apartment, offering an erotic touch . Enjoy 24/7 self-check-in, secure parking, and a rooftop with a heated pool for sunset relaxation. Fully equipped kitchen and numerous restaurants, coffee shops and markets nearby. Perfect for couples local looking for a quick get away or the best option for foreigners to start or end their Costa Rica trip .

Guest favourite
A dining setup is visible in the foreground with two white plates, utensils, and wine glasses placed on a textured gray surface. The background features a large window showcasing an expansive view of the city with greenery and mountainous scenery. A cozy seating area with a gray couch and a wooden table is also present.
Loft in Curridabat
4.91 out of 5 average rating, 266 reviews

Elegant loft in the heart of the city with pool

Welcome to your oasis of tranquility! Enjoy this elegant and centrally located accommodation with stunning mountain views, perfect for relaxing and unwinding. This space is designed to give you maximum comfort, with all the necessary amenities to make your stay unforgettable. Its location is ideal, as it places you close to restaurants, shops, and local attractions. Come and enjoy a unique experience in this charming retreat!

Superhost
A modern kitchen area includes a central island with two place settings. Decorative shelving holds small plants, while a cozy seating area is seen through large windows. Natural light fills the space, highlighting the combination of blue and white walls, and contemporary décor.
Apartment in Mata Redonda
4.84 out of 5 average rating, 143 reviews

New Bohemian Studio Best Views

SECRT Tower in Sabana is the absolute best tower in San Jose very close to Parque La Sabana (400 mtrs / 0.3miles). 20 min from Airport. Great, safe location. Very accesible, walking distance to restaurants, stores, pubs, supermarket, gas stations, etc. Apt is fully equipped. Free parking. Hot water. Coffee is on the house! Both living room and bedroom have TVs, with Netflix and Disney+ included and wifi speeds of 200MB

Popular amenities for Guadalupe rentals with a pool

Quick stats about vacation rentals with a pool in Guadalupe

  • Total vacation rentals

    Explore 70 vacation rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    60 of Guadalupe vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Guadalupe rentals

  • 4.8 Average rating

    Guadalupe stays are highly rated by guests—averaging 4.8 out of 5!

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