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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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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.
Flat in Urbanización Castro
4.97 out of 5 average rating, 182 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.
Flat in San Pedro
4.93 out of 5 average rating, 126 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
Flat in San José
4.95 out of 5 average rating, 131 reviews

Cálido estudio en Barrio Escalante

Vive la experiencia de Barrio Escalante, la zona más vibrante y gastronómica de la ciudad. Este apartamento combina elegancia y confort, ofreciéndote un espacio ideal para descansar después de explorar restaurantes, cafeterías y bares únicos, todos a pocos pasos de tu puerta. Todo en un piso 13 con una hermosa vista con los mejores atardeceres y sin dejar de lado la posibilidad de tener acceso autopistas que conectan con otros destinos turísticos cercanos, como volcanes, montañas y playas.

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
4.9 out of 5 average rating, 401 reviews

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.

Guest favourite
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
4.86 out of 5 average rating, 603 reviews

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

There is no better way to experience the beauty of San Jose than by sleeping in the heart of the city with a spectacular vista of the north of the capital. The landscape of the Irazú volcano on the horizon will be the perfect complement to enjoying the sunrise in your bed. This apartment is perfect to start your experience in Costa Rica, relax after a business trip, or spend a romantic night with your partner. All from a privileged area within a walking distance of restaurants and shops.

Guest favourite
A modern kitchen with sleek dark cabinetry and stainless steel appliances is complemented by barstools with yellow upholstery. The cozy living area includes a light-colored sofa and a decorative table, with a vase of flowers adding a touch of color. Natural light fills the space.
Flat in San José
4.96 out of 5 average rating, 135 reviews

Chic Escape in Trendy Barrio Escalante

Live Like a Local in the Heart of San José Welcome to our apartment in the vibrant and walkable neighborhood of Barrio Escalante. San José’s trendiest cultural and gastronomic district. Whether you’re here to explore the city, enjoy delicious food or simply relax, this thoughtfully designed apartment offers the perfect balance of comfort, style, and local experience. You will find yourself at walking distance from San Jose’s major attractions and some of the citie’s best restaurants

Guest favourite
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.
Loft in Curridabat
4.85 out of 5 average rating, 454 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.

Top guest favourite
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.
Flat in Carmen
4.89 out of 5 average rating, 479 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.

Top guest favourite
A modern living area features a comfortable gray sofa positioned opposite a large television. A small coffee table sits in front, accompanied by a decorative plant. Panoramic windows offer a view of the city lights in the distance, enhancing the room's spacious layout.
Loft in Curridabat
4.98 out of 5 average rating, 114 reviews

Apartment with excellent location. AC/wifi

Your 23rd-floor retreat with spectacular views! Wake up every morning in a cozy apartment located on the 23rd floor, where the sweeping views of the city from the balcony provide the perfect backdrop for your morning coffee or a sunset drink. Its location is perfect: just steps away are restaurants serving a variety of cuisines, a shopping center with a supermarket, pharmacy, and hospital, all within walking distance, making your stay convenient and worry-free.

Guest favourite
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.
Apartment in Rohrmoser
4.91 out of 5 average rating, 459 reviews

City ​​view, A/C near the airport, 1903

It is an apartment with an excellent distribution and a modern and contemporary aspect, located near the La Sabana Metropolitan Park, an area with excellent restaurants, entertainment venues, and very close to shopping centers, Juan Santamaría airport, etc; It is on the 19th floor, with a view to the east, the mountains and the city steal the show at all hours of the day, without a doubt the sunset and night are the favorites for their colors and lights.

Superhost
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.
Flat in Curridabat
4.9 out of 5 average rating, 102 reviews

Apto con excelente vista, A/C, parqueo incluido

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.

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.
Flat in San Pedro
4.93 out of 5 average rating, 295 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 .

Popular amenities for Guadalupe rentals with a pool

When is the best time to visit Guadalupe?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$73 SGD$73 SGD$74 SGD$66 SGD$61 SGD$65 SGD$63 SGD$64 SGD$63 SGD$68 SGD$72 SGD$79 SGD
Avg. temp22°C23°C24°C24°C24°C24°C24°C23°C23°C23°C23°C23°C

Quick stats about holiday rentals with a pool in Guadalupe

  • Total holiday rentals

    Explore 80 holiday rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    80 of Guadalupe holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Guadalupe rentals

  • 4.9 Average rating

    Guadalupe stays are highly rated by guests – averaging 4.9 out of 5!