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Holiday 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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Top guest favourite
Villa in Isla Verde
5 out of 5 average rating, 122 reviews

Gated Parking Heated Pool Generator Beach Walk

Everything you need for an effortless Puerto Rico stay. Minutes to Isla Verde Beach, with pool access and all your beach essentials ready. 🌊 Walk to Isla Verde Beach: close to top spots 🏊‍♀️ Heated pool access; sparkling clean, perfect to unwind 🧼 Impeccably clean: spotless and exactly as pictured 🔐 Easy, stress-free arrival 🏖️ Beach essentials included: chairs, umbrella, towels + cooler ⚡ Reliable essentials: Power generator backup + water cistern 💬 Super responsive host: fast, attentive

Top guest favourite
A private outdoor area features a turquoise pool surrounded by smooth stone flooring. Comfortable seating with tropical-patterned cushions is positioned nearby, alongside potted plants. Natural light filters in, enhancing the tranquility of the space.
Home in Santurce
4.9 out of 5 average rating, 274 reviews

Steps to Beach, 3BR/3BA, Own Pool, Parking, Gen

3 bedroom/3 bath duplex in trendy Ocean Park/Condado area just steps from the beach! Less than 10 minutes from the airport and Old San Juan, plus: *Own pool *Free parking *Private home gym *Beach gear *Weber gas grill *Full kitchen *Master suite with king bed and office space *Junior suite with queen bed *Third room with double bed *Queen size sofa-bed in living room *AC in every room *Washer/dryer in unit *Gated community Family-friendly, close to nightlife, and the best beach in San Juan!

Top guest favourite
The serene private patio features a shallow plunge pool surrounded by tropical plants and decorative stones. A textured green outdoor shower is visible, and a low wall separates the space from the vibrant greenery beyond, creating a secluded retreat for relaxation.
Bungalow in Ocean Park
4.99 out of 5 average rating, 117 reviews

Jungle Bungalow | 1BR Suite | Private Plunge Pool

Located just blocks from the vibrant Ocean Park Beach, our chic studio bungalow perfectly combines urban convenience with tropical serenity. Step into your private plunge pool or explore Calle Loiza's bustling streets, famous for eclectic dining and unique shopping. Your queen-sized bed features plush comfort with en-suite bathroom, providing a personal retreat. Enjoy the lush garden patio hanging egg-chairs for serene evenings, making every day of your stay memorable and relaxing.

Top guest favourite
An aerial view captures the beachfront townhouse, showcasing its private rooftop and surrounding palm trees. The tranquil ocean extends in the background, blending with soft blue skies. The townhouse features a combination of outdoor terraces and green space, emphasizing its proximity to the beach.
Townhouse in Ocean Park
4.99 out of 5 average rating, 137 reviews

Ocean Park Beachfront Paradise | Steps to the Sand

This Beach Front Townhouse is located in Ocean Park. One of Puerto Rico’s sought out locations! It is perfect for group trips as well as families looking for the perfect getaway! The Town House is in a gated community which means you will be guaranteed a safe trip. Private parking will be provided. The unit is a 10 minute drive from the airport as well as Old San Juan. You will have a private rooftop facing the ocean and a shared pool on the ground floor to use at your convenience.

Top guest favourite
An open living space features a king bed with neutral bedding, accompanied by a large sofa and a 50-inch TV. A dining table for two is positioned near the well-equipped kitchen. Floor-to-ceiling windows allow natural light and views of surrounding greenery.
Flat in San Juan Antiguo
4.93 out of 5 average rating, 122 reviews

King Bed Loft | by Old SJ & Escambrón Beach | Pool

Keep it simple at this peaceful and centrally-located place. Condado is one of San Juan's high-end areas packed with tourists, so people are on the street 24/7. This listing is next to Old San Juan, Escambrón Beach, and many other prime attractions! The building has a backup generator and water cistern in case of power and/or water outages. The unit is for two guests, and having more guests is prohibited. Additional guests who stay against the rules pay $50 per night.

Guest favourite
A rooftop pool area is featured with a small turquoise pool and an open terrace overlooking the ocean. Comfortable seating options are present, including lounge chairs and a shaded area with a cushioned sofa. Lush greenery and distant palm trees enhance the tranquil setting.
Flat in Santurce
4.85 out of 5 average rating, 254 reviews

Spectacular! Roof Pool, 10 steps to Beach, Groups

My place is 10 steps to the Ocean park beach, family-friendly activities, volley on the beach, kitesurf, windsurf, full of restaurants walking distance, nightlife, public transport, 10 min. to the airport. If you come with pets we need to know in advance and you will pay $200 per pet upon arrival in cash. I have free parking upon request before arrival. High velocity WIFI. 24/7 care and water tanks and plant (since Maria the companies cut water and electricity often)

Top guest favourite
Home in Carolina
4.99 out of 5 average rating, 178 reviews

Hilltop Cabin w/ Pool & Views – 18 Mins to Airport

✈️ 18 min to airport & 🏖️ top beaches 🏊 Private pool, loungers & hammocks 🌿 Peaceful countryside, just 5 min to city 🌴 45 min to El Yunque & Luquillo Beach 🏡 Hilltop cabin with ocean & mountain views 🛏 Queen bed + full pull-out bed (sleeps 4) 🍽 Indoor + outdoor dining for 4 with views 🚿 Outdoor shower (perfect after the beach) 🌅 Stunning sunrise views from elevated setting ⚡ Fast WiFi, A/C, Smart TV & gated parking 🪑 Beach chairs, cooler & beach towels

Top guest favourite
A tranquil private pool reflects the clear blue sky, surrounded by lush greenery and palm leaves. The modern apartment's large glass windows allow for abundant natural light, while a shaded outdoor seating area and hammock can be seen beside the pool.
Flat in Ocean Park
4.99 out of 5 average rating, 286 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.

Superhost
A custom soaking tub is set in a sunlit corner, surrounded by greenery and textured walls. A tall plant stands nearby, accompanied by a terracotta pot. Natural light filters through the overhead skylight, casting soft shadows across the space.
Hotel room in Ocean Park
4.87 out of 5 average rating, 131 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.

Guest favourite
A spacious terrace is shown, featuring a dining table and white chairs, with views of the turquoise sea and skyline. Lush greenery is visible along the edge, and a small lounge chair is placed for relaxation under partially covered awning, inviting enjoyment of the outdoor space.
Apartment in San Juan Antiguo
4.96 out of 5 average rating, 118 reviews

Romantic Oceanfront Private Patio Full Generator

This oceanfront loft is in the cosmopolitan neighborhood of Condado (San Juan) and is walking distance to a great variety of restaurants, bars, entertainment venues, water sports, movie theaters, and zip lines. It has the most amazing terrace, partially uncovered, so you can sunbath in style while contemplating the turquoise sea. It offers stunning water views from the inside as well as from its patio.

Top guest favourite
A spacious pool area features a heated saltwater pool accompanied by a jacuzzi. Comfortable lounge chairs are positioned around the pool, with lush palm trees providing shade. A modern covered terrace offers seating options for relaxation next to the scenic outdoor landscape.
Villa in Carolina
5 out of 5 average rating, 159 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!

Guest favourite
The living area features a brown leather couch complemented by a round coffee table and decorative elements. A ceiling fan and modern light fixtures are present, along with plants that enhance the space. Glass doors open to a private outdoor area, blending indoor and outdoor environments.
Home in Hato Rey Central
4.89 out of 5 average rating, 116 reviews

Mid-Century Modern house

Experience the magic of a recently renovated 1962 house, meticulously designed in the Mid Century style, where nature and abundant natural light take center stage. Embrace the seamless integration of open spaces, lush greenery, and a patio that flawlessly blends with the interior. The house has 3 bedrooms. It can comfortably accommodate 6 people, (2 per room).

Popular amenities for Viejo San Juan rentals with a pool

When is the best time to visit Viejo San Juan?

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Avg. price$430 SGD$531 SGD$532 SGD$550 SGD$356 SGD$296 SGD$337 SGD$418 SGD$337 SGD$245 SGD$309 SGD$382 SGD
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Quick stats about holiday rentals with a pool in Viejo San Juan

  • Total holiday rentals

    Explore 30 holiday rentals in Viejo San Juan

  • Nightly prices starting at

    Viejo San Juan holiday rentals start at $166 SGD per night before taxes and fees

  • Verified guest reviews

    Over 930 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Viejo San Juan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Viejo San Juan rentals

  • 4.7 Average rating

    Viejo San Juan stays receive an average rating of 4.7 out of 5 from guests

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