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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.
Flat in California
4.88 out of 5 average rating, 344 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.
Flat in Barrio Escalante
4.9 out of 5 average rating, 546 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
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
4.96 out of 5 average rating, 135 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 spacious bed with neutral-toned bedding is positioned near large glass windows, offering a nighttime city view filled with twinkling lights. Soft curtains frame the windows, complementing the warm color palette of decorative pillows arranged on the bed.
Home in Curridabat
4.92 out of 5 average rating, 132 reviews

Smart loft en el corazón de la Ciudad A/C y wifi

Disfruta de la tranquilidad de este smart loft, elegante y céntrico con vista a la ciudad! Ideal para relajarse. Cuenta con todos los servicios necesarios para hacer de tu estadía la más agradable con la más alta calidad. Su ubicación es favorable ya que se encuentra cerca de restaurantes, centros comerciales y supermercados. Está a solo 15 min del casco central de San José. Cuenta con una gran cantidad de amenidades como piscina temperada, cine, sala de estudio, gimnasio y área de coworking.

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, 342 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.

Top guest favourite
A cozy sitting area features a brown upholstered chair and a small wooden side table. Decorative elements include green plants and colorful throw pillows. A large window provides views of the outdoor landscape, with distant mountains visible under a cloudy sky.
Flat in Barrio Escalante
4.9 out of 5 average rating, 120 reviews

21st Floor Cozy Apartment w A/C

Your home away from home awaits you. An industrial design unit with both antique and contemporary accents are throughout this cozy space to help make your experience unforgettable. Welcome to this tastefully decorated sanctuary located in San José’s Barrio Escalante district, known for its eclectic cuisine and selection as one of the world’s “Coolest Neighborhoods” by Time Out magazine. This unit is perfect for singles and couples. Enjoy the breathtaking sunsets from the private balcony.

Guest favourite
A modern living space features a large window that brings in natural light, framing a view of the surrounding landscape. Two armchairs and a couch in neutral tones offer seating. A stylish lamp provides illumination, and a small plant adds a touch of greenery.
Flat in Urbanización Castro
4.89 out of 5 average rating, 141 reviews

Apartamento favorito en la Ciudad

Moderno y completamente equipado apartamento en una de las zonas más céntricas y vibrantes de San José. El llamado corazón de la capital, ofrece inumerables zonas para caminar, y es uno de los puntos más llamativos para los foodies y apasionados de la gastronomía, con incontables cafeterías y restaurantes a pocos pasos de distancia. Este apartamento minimalista es perfecto para quienes buscan de un espacio cómodo y con las mejores amenidades.

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.
Flat in San Pedro
4.93 out of 5 average rating, 244 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
An outdoor rooftop pool is highlighted, featuring a sleek modern design with lounge chairs positioned alongside. The pool's water reflects the surrounding skyline and mountain views under a partly cloudy sky. Glass railings provide an unobstructed perspective of the scenic backdrop.
Loft in Curridabat
4.88 out of 5 average rating, 255 reviews

BeST RANkED SuPERHOST * 18th Floor * KInG sIZE BeD

Studio Apartment on the 18th floor. Peaceful and centrally-located place. KING SIZE BED GREAT VIEW of the mountains. The apartment is close to supermarkets, shopping malls, restaurants, and cafeterias. Located in a beautiful and fancy neighborhood. Close to bus stops and San Jose Metro-Area Fast Uber rides. *** This building is smoke free, therefore is not allowed to smoke in any location nor in the apartment ***

Top guest favourite
The living room features large windows offering expansive city views. A stylish, beige tufted couch and two plush orange chairs are arranged on a richly patterned area rug. Modern lighting fixtures enhance the contemporary design, while dark cabinetry provides functional storage.
Apartment in Rohrmoser
4.96 out of 5 average rating, 560 reviews

Architect's Apartment, 21st Floor, Amazing View

Increíble apartamento rediseñado por el Arquitecto Andrés Brenes, único en su tipo. Ubicado en el piso 21 con muebles de lujo y asombrosas vistas . Amplio espacio de sala, cocina y habitación. Zona muy transitable, cerca de parques, centros comerciales y restaurantes. Aeropuerto: A 16 km, serían 35 min aproximadamente, dependiendo del tráfico. Parque metropolitano La Sabana: 1km Parqueo Privado No A/C

Guest favourite
An outdoor pool spans the edge of a rooftop, offering panoramic views of the city and surrounding mountains at sunset. Sun loungers are positioned along the pool's edge, and elegant handrails provide access to the water's inviting surface.
Flat in Curridabat
4.88 out of 5 average rating, 133 reviews

Chic Bohemian Loft

Discover our Bohemian Sky Retreat on the 18th floor, a blend of bohemian elegance and comfort with stunning city views. Enjoy vibrant decor, a plush living area with a smart TV, and a fully equipped kitchen. The serene bedroom promises a restful night beside mesmerizing skyline views. Steps from cafes, dining, and attractions, this urban oasis offers an unforgettable city experience.

Guest favourite
A serene swimming pool is surrounded by lush greenery, featuring tropical plants that create a natural ambiance. The clear water reflects the sky, while the minimalist poolside design emphasizes the tranquil environment.
Serviced apartment in Rohrmoser
4.96 out of 5 average rating, 126 reviews

Beautiful view apartment with hotel amenities

Este lugar tiene una ubicación estratégica: ¡será muy fácil planear tu visita! Dispone de amenidades de hotel: piscina, gimnasio, sala de cine, área de trabajo, bbq, sala de masajes, salón para eventos. Es un espacio libre de fumado. Las mascotas no están permitidas.

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 $26 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    60 of Guadalupe holiday 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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