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Vacation rentals with a pool in Viejo San Juan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Viejo San Juan

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

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A spacious pool area is surrounded by palm trees, with lounge chairs arranged neatly along the edge. The pool features clear turquoise water and has shallow entry points. A shaded gazebo can be seen in the background, providing an inviting space for relaxation.

Apartment in Cangrejo Arriba

4.88 out of 5 average rating, 232 reviews

Island Living: Beachfront Ocean View w/Parking

Hi. Looking for a beachfront apartment? Look no further! This is a beachfront 1 bedroom apartment that sleeps 2 in the best beach in San Juan! 15min from Old San Juan, 7min from the Airport, near shops, restaurants, hotels, casinos, nightlife, and a vibrant walking district. Hear the ocean waves, feel the breeze, enjoy the sun! The building has a private beach entrance, basketball court, tennis court (currently closed), pool, gazebos, bbq area, and more! Welcome to the Island Living experience!

A clear swimming pool is featured in the foreground, surrounded by gray lounge chairs under a bright blue sky. Lush greenery and palm trees frame the area, while tall residential buildings provide a backdrop, enhancing the open and airy feel of the space.

Loft in San Juan

4.95 out of 5 average rating, 503 reviews

⭐️SPECTACULAR CHIC STUDIO PROFESSIONALLY SANITIZED⭐️

You will love staying in this chic apartment that was carefully re-designed with a lot of passion & love ❤️. Rest assured that we take cleaning and sanitizing procedures very seriously and our Housekeeping Manager is freak about it. With beautiful blue sky & ocean views during the day and a magnificent city view during the night, just 10min from SJU airport, it will be your perfect spot is to enjoy the island at it's best. Walk and enjoy the beach, Casinos, Restaurants and shops around Condado.

A large swimming pool is surrounded by tropical foliage and palm trees, reflecting the blue sky. The building’s architecture features a blend of white walls and glass doors, providing a view of the inviting outdoor area. People can be seen enjoying the pool.

Apartment in San Juan

4.95 out of 5 average rating, 104 reviews

Perfect apt for a stay in San Juan!

Cozy 1 br/1 bth apartment. Semi-loft style with sofa bed in living room. Located in San Juan's trendy Condado Beach neighborhood. Building designed by acclaimed architect Henry Klumb, this apartment comes fully equipped and is walking distance to the beach, lagoon, restaurants, cafes, and bars. Condado is just 4 miles from the airport and Old San Juan. There's a large pool and bistro café. Paid parking is available right next door and there are two car rental spots less than a 5 min walk.

A balcony view features two wooden lounge chairs and a small table, overlooking a sandy beach lined with palm trees. The vibrant blue ocean stretches beyond, complemented by a clear sky with scattered clouds.

Apartment in Cangrejo Arriba

4.93 out of 5 average rating, 107 reviews

Beachfront Condo with Balcony 15 min from San Juan

Marvera is located just 5 minutes away from the SJU airport, our cozy OCEANFRONT one-bedroom, one-bathroom retreat is the perfect escape for both relaxation and adventure. Our prime location is only steps aways from Isla Verde beach and offers easy access to nearby hotels, casinos, and a variety of restaurants. For history enthusiasts, the charming streets and iconic landmarks of El Viejo San Juan are just a short 15 minute drive away. Follow us on IG @airbnbmarvera for videos!

The open living-dining area features a spacious sofa and a dining table surrounded by four chairs. Large glass doors provide access to the balcony, where high-top chairs and a small table overlook the ocean. Modern pendant lights hang above the dining table.

Condo in San Juan

4.87 out of 5 average rating, 119 reviews

Palms & Ocean View 1br 1bth + Pool + Beach Access

In the heart of Condado, with direct private access to the Condado beach. The building is on Ashford Ave., surrounded by great restaurants, cafes, and bars. At walking distance, you have supermarkets (5 min), Calle Loiza St. with vibrant nightlife (6 min), and La Placita de Santurce with also great nightlife (15 min). At driving distance, you have the Convention Center & El Distrito (10 min), Old San Juan (15 min), Hato Rey Milla de Oro (15 min), and the airport (15 min).

A private pool area is surrounded by lounge chairs and tropical greenery. Sunlight reflects off the clear blue water, creating a relaxing atmosphere. Tall buildings can be seen in the background, suggesting a central location.

Apartment in San Juan

4.83 out of 5 average rating, 251 reviews

Luxury Ocean-View @ Condado Ashford, free parking

Modern & fully renovated apartment with new kitchen, new bathroom and new furniture. Luxury Studio apartment with ocean view, located in the heart Condado, prime location. One free parking spot included. 2-minute walk to the beach right across the street. Walking distance to all local restaurants, bars, casino. Health food store (called Fresh Mart, very similar to Whole Foods and Trader Joe's) right next to the lobby. Walgreens & CVS within 2 blocks walking.

Top guest favorite

A private outdoor area features a heated pool surrounded by a smooth patio. A hammock hangs nearby under a shaded pergola, while a dining table and lounge chairs are positioned for relaxation. Lush greenery enhances the tranquil atmosphere, offering a serene retreat.

Apartment in San Juan

4.99 out of 5 average rating, 252 reviews

Best location with pool, steps from beach!

Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.

An outdoor pool area is visible, featuring a swimming pool surrounded by a tiled deck. A circular table with chairs is positioned nearby, complemented by a pink umbrella. Lounge chairs are arranged along the side of the pool, set against a backdrop of buildings.

Apartment in San Juan

4.97 out of 5 average rating, 202 reviews

King Suite Steps from the Beach w/ Parking

Enjoy a stylish experience at this centrally-located studio. In the heart of the Condado neighborhood. As soon as you walk out the front door you are immediately immersed in the lively energy of Puerto Rico. It's steps from the beach and the neighborhood is filled with delicious restaurants and great bars. Please keep in mind the parking provided is not in the building. It is one block away at the Marriott Hotel.

A serene outdoor space features a sculptural pool surrounded by white walls. A gentle staircase leads up from the pool area. Lush plants are positioned thoughtfully alongside a wooden chair, inviting relaxation under the bright sky.

Hotel room in San Juan

4.88 out of 5 average rating, 117 reviews

Design Suite「 POOL」Walk to Beach | DUNA by DW

If this apartment-plus were a perfume it would smell like juniper, cactus water, fennel seeds, slot canyons and homemade tortillas clasped in warm sunlit terracotta. Everything about this king-size suite is deep, sandy, and divine. With two private terraces, a bedroom, bath, full kitchen, custom soaking tub, hammocks, and more, the Dreamer can mesmerize up to three guests with elegant, laidback allure.

Top guest favorite

Villa in Cangrejo Arriba

5 out of 5 average rating, 130 reviews

Luxury waterfront villa with dock and heated pool

Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock to a serene lagoon. It is just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. Equipped with a generator and cistern for peace of mind. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

Top guest favorite

A refreshing pool area is surrounded by natural greenery, with stone accents and a sunlit patio. The pool features clear water and a small seating area, creating an inviting outdoor space. Lush foliage frames the scene, enhancing the serene atmosphere.

Home in Cangrejo Arriba

4.98 out of 5 average rating, 121 reviews

Villa Estrella PR (near Airport & Beach)

Diviértete con toda la familia en este alojamiento con estilo. Esta cerca de todo lo esencial como el Aeropuerto y Playas (5 minutos), Viejo San Juan, Plaza Las Américas (15 minutos). Localizado cerca de varios restaurantes con prestigio como Bebo’s BBQ, Metropol, y el área turística de Piñones donde podrán encontrar comida típica de nuestra isla.

Top guest favorite

A bright living area showcases expansive glass doors that open to a private balcony with views of the ocean. Comfortable seating arrangements include a sectional sofa and two outdoor chairs. A modern coffee table sits centrally on a textured rug, enhancing the open and inviting atmosphere.

Condo in Cangrejo Arriba

4.95 out of 5 average rating, 101 reviews

Deja Blue BeachFront Apartment @ Isla Verde (Green Island)

🏝️Apartment Steps of the Beach 🏖️😎 🛫3 minutes Away from Airport ✈️ Deja Blue is an amazing recently remodeled BeachFront Apartment with 2 bedrooms and 1 bath on Isla Verde Beach. You will love the views from every room in the apartment and our recently renovated living room and kitchen. Enjoy morning or sunset walks on the beach.

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Popular amenities for Viejo San Juan rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features two comfortable sofas in blue and rust colors, arranged around a glass coffee table. Neutral curtains frame the windows, which allow natural light to fill the space. A piece of artwork and a decorative vase enhance the ambiance.

Home in Guaynabo

4.79 out of 5 average rating, 151 reviews

Super comfortable Family Home w/ private pool

A refreshing pool features built-in lounge chairs, allowing for relaxation while enjoying the water. A covered seating area is positioned adjacent to the pool, with comfortable furniture. A grill is visible in the background, set against a backdrop of greenery and a clear sky.

Home in Cangrejo Arriba

4.85 out of 5 average rating, 122 reviews

House of Angels

A tranquil pool area is highlighted by a stylish stone water feature, where water cascades gently into the pool. Lush, tropical plants are visible in the background, complementing the serene atmosphere of the space.

Home in Levittown

4.93 out of 5 average rating, 140 reviews

La Pompa Beach House Beautiful Residence with Pool

Home in San Juan

4.92 out of 5 average rating, 153 reviews

Luxury Casa Caliad

A relaxing pool area is featured with a sparkling pool surrounded by a well-maintained lawn. A hanging chair is positioned near the pool, and a shaded seating area with lounge chairs is visible in the background. Clear blue skies complement the outdoor setting.

Home in San Juan

4.96 out of 5 average rating, 174 reviews

Costa Escondida

Top guest favorite

The exterior of the house showcases a modern architectural design with a prominent teal front door. Clean lines and a well-maintained garden, featuring decorative white stones and small shrubs, accentuate the entrance. A paved walkway leads up to the steps of the entryway.

Home in Carolina

4.97 out of 5 average rating, 108 reviews

Villa Turquesa- Private Pool

The image displays a private pool area featuring a circular jacuzzi and a larger swimming pool, surrounded by lush tropical vegetation. The exterior of the two-story house is visible, with multiple glass doors providing access to the outdoor space, enhancing natural light.

Home in Trujillo Alto

4.91 out of 5 average rating, 195 reviews

Unique luxury house-Private pool-Power generator

The outdoor pool area features clear blue water, bordered by light-colored stone tiles. Several dark chairs are positioned along the side, providing seating for relaxation. Green foliage is visible in the background, complementing the bright sky.

Home in Carolina

4.85 out of 5 average rating, 123 reviews

The Leaves Apartments #2

Condo rentals with a pool

Two glasses filled with water and ice are placed on a balcony railing. In the background, the turquoise ocean meets the sandy beach, framed by lush green palm trees swaying gently in the breeze under a clear blue sky.

Condo in San Juan

4.88 out of 5 average rating, 182 reviews

High Rise Ocean Waves In Condado

A large outdoor pool with clear blue water is framed by a spacious tiled deck. Several lounge chairs are arranged alongside the pool, and a small waterfall feature adds interest. Nearby, tropical plants provide a touch of greenery against the surrounding buildings.

Condo in San Juan

4.78 out of 5 average rating, 276 reviews

Ashford Imperial. Best Location.

An aerial view showcases a large pool area surrounded by lounge chairs, with a basketball court adjacent. Beyond the pool, the sandy beach is bordered by palm trees, and the ocean stretches out in the background, creating a serene coastal environment.

Condo in Cangrejo Arriba

4.95 out of 5 average rating, 178 reviews

Ocean View Paradise in Isla Verde, Puerto Rico!

Top guest favorite

A large swimming pool is visible, surrounded by palm trees and well-maintained landscaping. The clear blue water reflects the sunny sky, with lounge chairs positioned along the poolside. In the background, a view of the beach can be seen, adding to the peaceful atmosphere.

Condo in Cangrejo Arriba

4.95 out of 5 average rating, 163 reviews

Isla Verde Beachfront Studio near restaurants,bars

The pool area features a large swimming pool surrounded by lounge chairs with blue cushions. Several palm trees provide shade, and a blue umbrella is positioned beside a round table. A soft sunset glow casts a calming ambiance over the scene.

Condo in San Juan

4.85 out of 5 average rating, 334 reviews

Beautiful apartment in Condado with beach access!

Top guest favorite

Condo in Cangrejo Arriba

4.93 out of 5 average rating, 152 reviews

💕Ocean Front Isla Verde Beach Remodeled Pool Pkg

A spacious pool area features a bright blue pool surrounded by light-colored stone tiles. Several lounge chairs are positioned around the pool, providing ample space for relaxation. Nearby, tall buildings rise in the background, creating a vibrant urban atmosphere.

Condo in San Juan

4.9 out of 5 average rating, 158 reviews

Condado - Ashford Imperial - Epic ocean views

A large swimming pool is surrounded by palm trees and lounge chairs, with guests relaxing under the sun. The clear water invites leisure activities, while a low wall and several potted plants create a tropical ambiance nearby.

Condo in San Juan

4.94 out of 5 average rating, 390 reviews

Ashford, San Juan - “The Place”!

Other vacation rentals with a pool

A modern living area features a light-colored sofa, two ottomans, and a glass dining table surrounded by gray chairs. Large windows offer sweeping ocean views, and a floral arrangement adds a touch of color to the bright and airy space.

Apartment in San Juan

4.95 out of 5 average rating, 37 reviews

Make our home YOUR HOME ON the OCEAN!

A modern kitchen space features a sleek marble countertop with two wooden stools. Minimalist cabinetry is complemented by soft lighting, creating an inviting cooking area. The wall showcases a decorative element, enhancing the overall contemporary design of the space.

Apartment in San Juan

5 out of 5 average rating, 6 reviews

Modern Studio in Condado

A spacious bedroom features a comfortable bed adorned with soft pillows and an artistic mural reflecting tropical themes. Natural light floods the room through glass doors, which offer a view of the ocean. A cozy seating area complements the vibrant decor.

Condo in San Juan

4.96 out of 5 average rating, 85 reviews

Rare Beachfront Getaway w Pool, Gym, + Balcony!

Top guest favorite

A modern living area features a comfortable sectional sofa, adorned with decorative pillows. A coffee table holds a platter of fresh fruit and two colorful glasses. Large windows allow natural light to fill the space, revealing views of the surrounding cityscape.

Apartment in San Juan

5 out of 5 average rating, 71 reviews

Great 1 bedroom apt in Condado area w/pool

A bright bedroom is equipped with a spacious bed adorned with a textured blanket. Two bedside tables with lamps flank the bed, and a colorful piece of wall art features beach-themed imagery. Large windows allow natural light to fill the room, accompanied by green plants enhancing the decor.

Apartment in San Juan

4.99 out of 5 average rating, 71 reviews

Penthouse Beach Retreat

An open living area features a comfortable sofa paired with colorful cushions, a glass coffee table, and a dining space with four chairs. Large windows provide stunning ocean views, while modern pendant lights hang from the ceiling. A granite kitchen counter adds a touch of elegance.

Condo in San Juan

4.87 out of 5 average rating, 15 reviews

Luxury OceanFront @ 17th Floor Condado

A serene balcony with a round table and four chairs overlooks a shimmering lagoon. The space is framed by large glass doors, allowing ample natural light to fill the area. Scenic views of the water and city skyline create a tranquil atmosphere.

Apartment in San Juan

4.88 out of 5 average rating, 34 reviews

Waterfront Getaway Prime Location+Balcony+Pool

A private outdoor pool is illuminated in gentle blue light, surrounded by sleek white walls and tropical greenery. Large glass doors provide a view into the interior space, where soft lighting creates a welcoming ambiance.

Casa particular in Trujillo Bajo

5 out of 5 average rating, 8 reviews

Villa Bali III King Suite Private Pool Heated

Quick stats about vacation rentals with a pool in Viejo San Juan

Total rentals
40 properties
Nightly prices starting at
R2,122 ZAR before taxes and fees
Total number of reviews
1.4K reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

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