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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
Loft in Curridabat
4.93 out of 5 average rating, 137 reviews

Loft with a balcony, panoramic view, and private parking

We offer you an apartment on the 18th floor, with a panoramic view and cool breeze. 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% Superhost in Costa Rica, I guarantee fast and dedicated attention to make your stay memorable.

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, 559 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

Superhost
A cozy bedroom features a spacious bed adorned with a neutral-toned quilt and decorative pillows. A bedside table with a lamp stands beside the bed. Floor-to-ceiling windows offer views of the outdoor pool area and the surrounding landscape.
Loft in Francisco Peralta
4.88 out of 5 average rating, 124 reviews

Beautiful loft pool, gym and excellent location

Disfrute de una experiencia elegante en este lugar céntrico de San José, a poca distancia de los lugares más modernos, históricos y turísticos. Disfruta tranquilamente de un apartamento a estrenar con todo lo necesario para tu estancia. Tendrás un supermercado frente al edificio, pero también bares y restaurantes en Barrio Escalante. Acceso a excelentes amenidades: Gimnasio, 2 albercas, área de BBQ, firepit al aire libre, sala de cine, roof garden para disfrutar de vistas únicas de San José.

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
4.92 out of 5 average rating, 114 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 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, 124 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
The bedroom features a spacious bed with a navy blue headboard and a light quilt. A small bedside table with a lamp is positioned next to the bed. A cozy chair and a large mirror enhance the open feel, while ample natural light fills the space.
Loft in Curridabat
4.92 out of 5 average rating, 105 reviews

Cityscape iFreses, 20th floor! AC, TV and Pool

Discover this elegant, fully furnished apartment in one of the safest residential-commercial areas of San José, featuring 24/7 security. Situated in the exclusive iFreses Condominium, this apartment offers stunning city views and amazing amenities! Its strategic location places you within walking distance of shopping centers, supermarkets, coffee shops, restaurants, banks, and universities. Bus and taxi stops are just 50 meters away, and the train station is 200 meters away.

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
4.84 out of 5 average rating, 424 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.

Guest favourite
A modern living area features a comfortable sofa adorned with pillows and a textured throw. A decorative statue stands prominently, and a large wall clock is displayed above. Floor-to-ceiling windows provide a view of the city and access to a small balcony.
Flat in Bella Vista
4.88 out of 5 average rating, 254 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.
Flat in San Pedro
4.93 out of 5 average rating, 254 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 .

Top guest favourite
A modern living space is showcased with a sleek gray sofa facing a wall-mounted television. A minimalist dining area with two chairs is positioned near large windows offering expansive views of the cityscape and mountains. The concrete walls provide a contemporary ambiance.
Flat in Curridabat
4.96 out of 5 average rating, 125 reviews

Vivi's Hideaway

Enjoy this peaceful and centrally-located apartment, with sweeping 21st floor views of San Jose and the surrounding mountains. Fast internet, cool a/c, and a luxurious king sized, memory foam mattress await you after a day of exploring the Central Valley. Located in an exclusive high rise apartment, you will have access to one of the only rooftop pools in the central valley, a full gym, and inspiring coworking areas.

Top guest favourite
Loft in Curridabat
4.88 out of 5 average rating, 267 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 ***

Guest favourite
Flat in Barrio Escalante
4.82 out of 5 average rating, 133 reviews

URBN Cornerview city and mountain view-26th floor

Located in San Jose’s trendiest neighborhood, with all the amenities you need for a nourishing stay in the city. This is the ideal base for exploring the neighborhood of Barrio Escalante, with dozens of independent restaurants, cafes, and shops just steps away. The building amenities include: heated pool, gym, yoga room, coworking spaces, cinema, library, pet shower, laundry room and more.

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 1,590 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

    60 properties have a dedicated workspace

  • Wifi availability

    70 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!