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Holiday 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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Superhost
A modern bedroom features a spacious bed with fresh linens, positioned against a blue wall. A small nightstand is located on one side. A piece of wall art adds a decorative touch, while large windows provide views of the city and mountains.
Apartment in California
4.88 out of 5 average rating, 345 reviews

Balcony Sunset View 21st Floor Apartment

Located 21st floor of the stylish URBN Escalante building in the heart of San José, this modern one bedroom apartment has all the amenities for a pleasurable stay. Feel free to make use of the lobby with 24/7 concierge, heated pool, lounge area, co-working spaces, gym, yoga room, cinema, library, BBQ area and playground. Internet is available at all common areas as well as high-speed internet connection -100Mbps- in the apartment. 5-10 minute walk to Pubs, Restaurants and Supermarkets. Netflix👍

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, 189 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.

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, 138 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.

Guest favourite
A bright bedroom features a spacious bed with a dark blue throw blanket. Floor-to-ceiling windows provide an expansive view of the city and mountains. A bedside table holds a sleek lamp, while a textured area rug adds comfort to the wooden floor.
Apartment in San Pedro
4.92 out of 5 average rating, 109 reviews

Exclusive Apartment in Downtown Costa Rica

This penthouse is in one of the most exclusive areas of Costa Rica, excellent restaurants, the nightlife is intense, full of life. The apartment has places to work inside the building, a gym, an pool, 24-hour security and the apartment is spacious, the view it has is impressive! day or night "it takes your breath away" its minimalist decoration gives you peace in a world "full of complications" …you are a winner, and you deserve a night that brings you closer to that top level you deserve!

Top Guest favourite
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
4.91 out of 5 average rating, 345 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.

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, 138 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.

Superhost
A modern kitchen and living area are presented, featuring a spacious sofa, a wooden dining table, and a washer. Stainless steel appliances and white cabinetry create a clean, functional space. Large windows allow natural light to illuminate the area, with views of the surrounding city.
Apartment in Barrio Escalante
4.85 out of 5 average rating, 163 reviews

Stylish unit and great location in downtown.

Apt ubicado en los alrededores de Barrio Escalante, un hermoso lugar compuesto de casas antiguas, tiendas de diseño y restaurantes con diversas propuestas culinarias. Esto lo hizo digno de obtener el premio a "destino líder de México y Centroamérica a visitar 2019" en World Travel Awards. Es uno de los epicentros gastronómicos y culturales más importantes en San José, donde podrás escoger desde un hermoso lugar para tomar café hasta un distinguido bar para estar con tu pareja.

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, 118 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.

Top 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, 245 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, 264 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!

Popular amenities for Guadalupe rentals with a pool

Quick stats about holiday rentals with a pool in Guadalupe

  • Total holiday rentals

    Explore 70 holiday rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe holiday rentals start at $30 AUD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Guadalupe holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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