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Holiday rentals with a pool in San Juan

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in San Juan

  • Total holiday rentals

    Explore 30 holiday rentals in San Juan

  • Nightly prices starting at

    San Juan holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 910 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

    30 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!

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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Guest favourite
An inviting outdoor area features a private heated pool surrounded by tropical plants and potted flowers. Comfortable seating options, including a hammock and lounge chairs, are positioned around the pool, with a cozy dining area visible in the background under soft lighting.
Villa in Mata Redonda
4.96 out of 5 average rating, 139 reviews

Cheerful private 4-Bedroom Villa. Heated pool A/C

For a group or a cozy couple, this bright and spacious home delivers comfort and style. Located in a quiet, modern, and safe neighborhood, you’re just minutes away from downtown. Great restaurants are close by and a block away from new Microsoft tower. 4 bedrooms (A/C), sleeps up to 9 , 3 full bathrooms & private heated pool. Fully equipped modern kitchen, stocked with staples and more. Starts at $195 per night for up to 4 guests, $35 per extra guest. Cleaning included. Come dive into city life.

Top guest favourite
A bright living area features a light-colored sofa bed, paired with a minimalist black side table. Large windows are adorned with sheer white curtains, providing a view of vibrant trees outside. A floor lamp and small potted plant add subtle accents to the space.
Flat in Mata Redonda
4.96 out of 5 average rating, 165 reviews

NucleoSab IvoryApt-NearSJairport-FreeIndoorParking

Brand new luxury apartment at Nucleo Sabana. It has a minimalist style with all the appliances brand new, including A/C, 2 smart TVs. High speed internet with TVservice. Laundry room includes a washer/dryer, 2 in 1. It has a wonderful view to the top of the trees and the sky in the balcony. There is a river next to it so you can always enjoy the river sound. Complex: More than 30 amenities, including a gastronomic market(NucleoGastro). Located 10min from Juan Santamaría Int’l Airport (SJO).

Top guest favourite
A bright and airy living space is depicted, featuring a stylish side table and a decorative plant. A flat-screen TV is mounted on the wall, while a semi-open door reveals a glimpse of a bedroom. Light filters through floor-to-ceiling windows, enhancing the contemporary design.
Apartment in Mata Redonda
4.94 out of 5 average rating, 364 reviews

Charming Apartment w A/C Near to the Int. Airport

Bienvenido a este encantador y elegante apartamento, en el piso 24; con una decoración exquisita Cuenta con dos cuartos, con camas de alta calidad: una Queen y otra matrimonial. Y un sofá cama en la sala 1 espacio de parqueo La cocina está completamente equipada. Disfruta de tus habilidades culinarias con tus seres queridos La torre cuenta con extraordinarias amenidades como piscina temperada, gimnasio y cuartos temáticos Aeropuerto: 16 km, aproximadamente 35 minutos, dependiendo del tráfico

Guest favourite
An outdoor seating area is framed by a modern structure, overlooking a pool surrounded by lounge chairs. Umbrellas provide shade, and greenery is visible in the background, enhancing the relaxing environment.
Flat in Mata Redonda
4.85 out of 5 average rating, 332 reviews

15th Floor Apt / Amazing Views • 20 min to Airport

Experience San José from a modern apartment with panoramic city views in the exclusive Núcleo Sabana complex. Fully equipped with Wi-Fi 5G, Smart TV, full kitchen, and private parking. Enjoy premium amenities including a pool, gym, sauna, lap lanes, multi-sport court, karaoke room, and beautiful green areas. Located steps from La Sabana Park, and the National Stadium and any restaurants. Perfect for business travelers, couples, or anyone seeking comfort and style in Costa Rica’s lively capital.

Top guest favourite
A serene plunge pool captures reflections of the sky, with a gentle waterfall cascading into the water. Lush tropical plants frame the scene, while comfortable loungers invite relaxation. Expansive views of the mountains and sky create a tranquil backdrop.
Flat in Escazu
4.98 out of 5 average rating, 140 reviews

Escazú Studio w/ pool, nature & spectacular views

A Cozy, Stylishly appointed Studio, tucked into a 2-Acre Estate w/ one of the most Breathtaking Views in Costa Rica. It is sanctuary for Value-Conscious Solo Travelers, Digital Nomads, Medical Tourists or a Romantic Get Away. "Earth & Sky - Costa Rica" has 3 Boutique Listings and features a Sparkling Heated Saltwater Pool, Bright Gardens and Beautiful Terraces. The "Sugar Shack" is our most Budget Friendly space - peaceful and private, but minutes away from popular restaurants and shopping.

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 Mata Redonda
4.97 out of 5 average rating, 192 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
Apartment in Rohrmoser
4.94 out of 5 average rating, 344 reviews

Industrial 2BR perfect location w/AC + sunset view

Take a morning stroll in the park before heading back to your centrally-located, industrial 2 br apartment that will welcome you with high-speed wifi, top-of-the-line kitchen appliances, amazing decor, comfortable beds, and sunset views from a 12th floor overlooking the city. Not only will you have access to unparalleled amenities like a semi-Olympic pool, saunas, gym, and co-working space, you will be a walking distance from the best restaurants, coffee shops, and grocery stores in town.

Top guest favourite
A corner seating area features a light-colored sofa with a matching ottoman, positioned near a large window. Lush greenery is visible outside, complemented by gentle textures in the room, including a woven rug and a stylish floor lamp.
Flat in Uruca
4.93 out of 5 average rating, 192 reviews

Best View, Luxury, Full Amenities, Nearby Airport

Welcome to our stunning retreat in Sabana, the heart of San José! Enjoy a breathtaking NATURE VIEW from our cozy apartment, just 20 minutes from the airport. There are 8 international RESTAURANTS IN THE BUILDING, including a coffee shop! This tranquil sanctuary offers convenience and serenity. Relax on the balcony, take a refreshing dip in the POOL, stay active at the GYM, work in the dedicated space, or stroll through the beautiful GARDENS. Enjoy the wonders of San José. Book now!

Superhost
A modern kitchen area features a white island countertop with a stovetop, surrounded by sleek bar stools. A cozy living area with a gray sofa and decorative pillows is visible, alongside a window showcasing city views and palm plants adding a touch of greenery.
Apartment in Rohrmoser
4.9 out of 5 average rating, 472 reviews

City ​​view, A/C near the airport, 1903

It is an apartment with an excellent distribution and a modern and contemporary aspect, located near the La Sabana Metropolitan Park, an area with excellent restaurants, entertainment venues, and very close to shopping centers, Juan Santamaría airport, etc; It is on the 19th floor, with a view to the east, the mountains and the city steal the show at all hours of the day, without a doubt the sunset and night are the favorites for their colors and lights.

Top guest favourite
A modern studio is displayed with a cozy sleeping area featuring a spacious bed. A dining table is set with elegant glassware and decorative elements. Large windows allow natural light to brighten the room, complemented by soft curtains. A wall-mounted TV completes the inviting atmosphere.
Loft in Escalante
4.98 out of 5 average rating, 99 reviews

Apartment in Escalante Olive Loft 14th

A modern and elegant studio on the 14th floor, with an amazing sunset view. Located in the heart of Barrio Escalante, close to bars and excellent restaurants with a wide variety of cuisine, opposite one of the 100 best cafés in the world. Perfect for couples, solo travelers or digital nomads looking for comfort in a safe and walkable location. Escalante is the cultural and gastronomic epicenter of San José, with active local life at any time of the day.

Guest favourite
The entrance of the mansion features a circular driveway enhanced by a central fountain, surrounded by landscaping and soft evening lighting. The façade showcases warm colors, with windows gently illuminated as the sun sets on the horizon.
Villa in San José
4.84 out of 5 average rating, 192 reviews

Exclusive Tuscan Mansion in CR

Our Italian-Styled mansion is nestled among a lush mango-tree forest in gorgeous Santa Ana only 20min from airport. Features: - Indoor Pool (Heating Upon Request $100 extra per day and requires 24 hours of heating prior to use) - 6 Bedrooms - 6 Bathrooms - Large Living Areas - 5 min from highway 27 to beaches & rainforests - 15 min from Escazu and CIMA Hospital - 24/7 armed security - Huge Green Areas Heavenly!

Guest favourite
Flat in San José
4.87 out of 5 average rating, 297 reviews

Curated Luxury Stay on the 22nd Floor

Bienvenido a una experiencia sofisticada y cuidadosamente diseñada en el corazón de URBN Escalante. Cada espacio fue pensado para ofrecer una experiencia cálida, refinada y llena de estilo, combinando decoración cuidadosamente seleccionada, acabados modernos y una atmósfera acogedora que hace sentir el apartamento verdaderamente especial.

Popular amenities for San Juan rentals with a pool

When is the best time to visit San Juan?

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Avg. price$80 SGD$71 SGD$68 SGD$72 SGD$74 SGD$63 SGD$68 SGD$76 SGD$71 SGD$79 SGD$84 SGD$96 SGD
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