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Holiday rentals with a pool in Guadalupe

Find and book unique homes with a pool on Airbnb

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!

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
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, 127 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 Escalante
4.95 out of 5 average rating, 132 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 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 Escalante
4.96 out of 5 average rating, 136 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 Yoses
4.89 out of 5 average rating, 481 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, 116 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.

Top guest favourite
Flat in Heredia
4.97 out of 5 average rating, 157 reviews

Comfort & Style Near SJO Airport +Pool & Mtn Views

CR Stays Welcomes you to this fully-equipped studio just 4 miles from Juan Santamaría Airport. Enjoy breathtaking views of the Escazú mountains, a king bed, queen sofa bed, fast Wi-Fi, and air conditioning—ideal for 4 guests. The building boasts a gym, pool, BBQ terrace, private cinema, and meeting rooms. Minutes from Plaza Real Cariari’s shops and restaurants, and located in a prime business hub. 24/7 security for a safe, stylish, and comfortable stay.

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 modern bedroom features a plush bed with decorative pillows, complemented by stylish bedside lamps. A wall-mounted television is positioned opposite the bed, and large windows provide expansive views of the cityscape. Warm wood paneling adds a touch of elegance to the space.
Flat in Curridabat
4.86 out of 5 average rating, 139 reviews

Insta-worthy Apartment in a Beautiful Neighborhood

Welcome to your stylish and centrally located home away from home in San José, Costa Rica! Your custom apartment boasts a fully equipped kitchen. Relax in the comfort of the queen bed and enjoy the smart TV and FAST (200 mbps) internet. Amenities include a rooftop pool, gym, coworking area and 24/7 security for your peace of mind. Experience the best of the city with easy access to all the sights and sounds that San Jose has to offer.

Guest favourite
Flat in San José
4.87 out of 5 average rating, 377 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.

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, 296 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 private terrace is displayed with several lounge chairs and a small table, offering unobstructed views of the sunset over the city skyline. The dark stone flooring contrasts with the greenery of the potted plants, creating a serene outdoor retreat.
Flat in Rohrmoser
4.93 out of 5 average rating, 112 reviews

Sunset PrivateTerrace Ü Nunciatura

¡Nuevo! Vive la experiencia urbana en San José Descubre este apartamento con una espectacular terraza privada, idealmente ubicado en el corazón de la ciudad. A pocos pasos encontrarás parques, restaurantes, cafeterías, supermercados y más. ¡Todo lo que necesitas está a tu alcance! Además, estás a solo 15 minutos en coche del Aeropuerto Internacional Juan Santamaría. Nota: piscina temporalmente en mantenimiento

Popular amenities for Guadalupe rentals with a pool

When is the best time to visit Guadalupe?

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Avg. price$73 SGD$73 SGD$75 SGD$67 SGD$62 SGD$66 SGD$63 SGD$64 SGD$63 SGD$68 SGD$72 SGD$80 SGD
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