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Holiday rentals with a pool in San Juan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Juan

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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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, 125 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.

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, 158 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.

Superhost
A sunlit living room is highlighted by a cozy brown leather sofa, complemented by a natural fiber rug. A coffee table sits in front, while large glass doors offer a view of the cityscape and allow natural light to fill the space.
Flat in Merced
4.93 out of 5 average rating, 105 reviews

Nucleo Sabana, West City View, A/C, Pool & Gym 1BR

Take a morning stroll in the zen garden before heading back to your perfect location, boho chic 1 br apartment that will welcome you with high-speed wifi, top-of-the-line kitchen appliances, amazing decor, comfortable beds, and sunset views from an 11th floor overlooking the city. Not only will you have access to unparalleled amenities like a cinema, gym, library, bbq areas and co-working space, you will be a walking distance from La Sabana park, best coffee shops, and grocery stores in town.

Guest favourite
A spacious living area features a large gray sofa and a flat-screen TV mounted on the wall. Natural light floods the room through floor-to-ceiling windows, offering views of the surrounding cityscape. Houseplants are arranged on a sleek white entertainment unit, enhancing the inviting space.
Apartment in Rohrmoser
4.88 out of 5 average rating, 116 reviews

Luxury SkyView Apartment 2BR

The apartment is spacious and very comfortable; each room is equipped with an imported memory foam king mattress you melt into. The large sofa can easily sleep two people. The shower has a large natural raindrop spout allowing for an organic soothing cleanse. Our apt is 15 walking minutes to National Stadium and is surrounded by restaurants, bars and shopping centers. Amenities include private massage rooms, an illuminated pool, a bbq area, and a large gym. Central A/C and TVs in all rooms.

Top guest favourite
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.
Apartment in Barrio Escalante
4.9 out of 5 average rating, 144 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 favourite
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.
Flat in Carmen
4.94 out of 5 average rating, 115 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 favourite
A spacious living and dining area is presented, featuring a round table with four chairs and a comfortable grey sofa facing a wall-mounted TV. Light-colored cabinetry and appliances complement the modern décor, while an assortment of framed photos adds a personal touch.
Apartment in San José
4.91 out of 5 average rating, 108 reviews

Fully-Eqpd 2BR 2BA in Luxury GC w/Pool+Gym+24/7Sec

Welcome to Apartment 406, your stylish 786ft² (73m²) sanctuary in Costa Rica—the largest unit in the Bambú Rivera Residential Complex! Perfect for digital nomads and vacationers, this modern 2-bedroom apartment is fully equipped for a comfortable stay. With 24/7 security and a wealth of amenities, you're just a short distance from the city center and its attractions. Whether you're here to work, explore, or unwind, this is the ideal home base for your trip.

Guest favourite
The interior space features an open layout with a modern design. A comfortable gray sofa and a white accent chair are arranged around a round coffee table. A staircase leads to the upper level, while natural light floods the area through large windows, enhancing the room's brightness.
Loft in Rohrmoser
4.86 out of 5 average rating, 152 reviews

Art Loft - Luxurious Apt QBO Building, Rohrmoser

Stylish apartment in the nicest neighborhood of San Jose. The loft is in a new luxury tower with more than 10 amenities (co-work spaces, semi-olympic pool, therapeutic pool, Jacuzzi on different floors, children's garden, two gyms, and several other spaces). Supermarkets, banks, restaurants, Sabana Metropolitan Park, National Stadium, are all located nearby. Great for medical tourism, business travelers, or anyone who wants to visit San Jose.

Guest favourite
Apartment in Monserrat
4.82 out of 5 average rating, 152 reviews

Super view and WiFi, 2 bedrooms, 2 bathrooms and 2 parking spaces

Azenza Towers, Excellent location and security. 11th floor: excellent sunset view. 500 Mbps WiFi. VGA Monitor. 2 bedrooms, 2 bathrooms, 2 free covered garages 3 elevators 5 km from San José 7 km from Escazú 16 km from the International Airport 70 km from Pacific Beaches Close to major corporate centers in San José, Heredia and San José, as well as shopping malls, hotels and hospitals. Pool, yoga deck, gym, playground and work area. Roof Top.

Guest favourite
A modern living area features a flat-screen TV mounted on a textured stone wall. A wooden entertainment console holds decorative items, including a statue and a lamp. A potted plant adds a touch of greenery, complementing the surrounding decor.
Flat in Bella Vista
4.88 out of 5 average rating, 262 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, 263 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
Flat in Mata Redonda
4.94 out of 5 average rating, 186 reviews

Charming 30th Floor Apt, King Bed, AC, Parking

Cozy, delightfully decorated Alice In Wonderland inspired apartment! Located on the 30th floor, our comfortable one-bedroom apartment boasts amazing views of the city. Safe building, central location, within walking distance from the National Stadium, La Sabana park, restaurants, and supermarkets. SECRT Sabana is a funky building, famous for its fun Alice-themed common areas.

Popular amenities for San Juan rentals with a pool

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Quick stats about holiday rentals with a pool in San Juan

  • Total holiday rentals

    Explore 40 holiday rentals in San Juan

  • Nightly prices starting at

    San Juan holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 900 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of San Juan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across San Juan rentals

  • 4.8 Average rating

    San Juan stays are highly rated by guests – averaging 4.8 out of 5!