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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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Top guest favorite
Loft in Curridabat
4.93 out of 5 average rating, 132 reviews

Loft with a balcony, panoramic view, and private parking

We offer you an apartment with a panoramic view and cool breeze on a18 floor. This modern loft combines style and comfort with an integrated balcony, blackout curtains for added comfort, wifi, and private parking. On the 25th floor we have an infinity pool, iworking area and more. We are located in a safe and central area of Curridabat, where you will have everything at your fingertips. As a Top 10% Super Host in Costa Rica, I guarantee prompt and dedicated attention to make your stay unforgettable.

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
4.87 out of 5 average rating, 341 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👍

Superhost
An open, modern living space features a round wooden dining table surrounded by black chairs. A brown leatherette sofa is positioned against a white wall with recessed lighting. A glass-enclosed area is visible in the background, accompanied by a kitchenette equipped with a microwave and storage.
Apartment in Barrio Escalante
4.9 out of 5 average rating, 540 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

Top guest favorite
A modern living area features a comfortable sofa adorned with a cozy throw blanket. A decorative butterfly display is set on a textured side table, complemented by framed art of natural scenes and a floor plant. Soft lighting from a stylish lamp enhances the inviting atmosphere.
Apartment in Uruca Centro
4.98 out of 5 average rating, 115 reviews

Cozy Morpho Stay + tour tips/ AC / Parking /Center

Relájate y disfruta una experiencia con estilo Japandi. Escucha los pájaros y contempla las montañas al amanecer, vive los mejores atardeceres y una increíble vista nocturna, todo desde nuestro balcón! Ubicado en nueva y lujosa torre con modernas amenidades a tan sólo 10 min de teatros, museos y parques emblemáticos de la capital. Además puedes ir caminando o en bicicleta al parque de La Sabana o el Estadio Nacional. Con fácil acceso a la autopista, la cual te llevará en 25 min al aeropuerto

Guest favorite
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
4.97 out of 5 average rating, 127 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 favorite
Condo in Carmen
4.91 out of 5 average rating, 141 reviews

Luxury 14th-Floor Apartment with Views in San José

Discover tranquility in this centrally-located haven near Barrio Escalante. Enjoy a cozy retreat just steps from the city’s top restaurants, offering local and international cuisine. You will find a grocery store just in front of the main gate. Next to the building, there is a bowling and a Mall 5 minutes waking. Immerse yourself in culture with nearby museums, cinemas, and art scenes. You’re less than an hour from stunning natural attractions-volcanoes, mountains, and beaches await!

Guest favorite
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, 104 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!

Guest favorite
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, 333 reviews

Studio with a beautiful view

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 favorite
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, 132 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.

Guest favorite
A panoramic view of the city is showcased at dusk, with vibrant clouds illuminated by the setting sun. The skyline features a mix of tall buildings, while distant mountains rise in the background, providing a dramatic contrast against the colorful sky.
Apartment in Carmen
4.94 out of 5 average rating, 111 reviews

Penthouse in San Pedro, view of the gods. Luxury, A/C.

This special place is close to everything, making it easy to plan your visit. Luxury two-story penthouse 16 and 17!A/C. View of the gods! With a unique and privileged view, in the exclusive area of Los Yoses. Close to all the Escalante cuisine. Just 3 minutes from the city of San José. With a spectacular view of the mountains to the south of the city and the beautiful sunsets to the west. Just meters from supermarkets and restaurants, parking included for our customers.

Guest favorite
A spacious living area showcases a comfortable bed with blue accent pillows, facing a kitchenette with modern appliances. A dining table is positioned nearby alongside blue chairs. White shelving units provide storage, while a patterned chair adds a touch of style to the room.
Apartment in Curridabat
4.92 out of 5 average rating, 172 reviews

Ifreses Apartment: clean/balcony/WiFi/desk

The space is very comfortable as it is equipped with kitchen utensils, a work table, Wi-Fi, TV, air conditioning, an individual armchair, a two-person armchair, shelves, closets, etc. that make it very cozy. It also has a balcony with sliding doors that allows you to enjoy beautiful views of San José and the mountains, incredible sunsets and fresh air. Most of the ratings highlight the cleanliness of the space, something we particularly care about offering.

Top guest favorite
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
4.92 out of 5 average rating, 237 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

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 ﺩ.ﺇ73 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 & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Guadalupe vacation rentals include wi-fi 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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