
Holiday rentals with a pool in Viejo San Juan
Find and book unique homes with a pool on Airbnb
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 $227 NZD per night before taxes and fees

Verified guest reviews
Over 1,080 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Viejo San Juan holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Viejo San Juan rentals

4.6 Average rating
Viejo San Juan stays receive an average rating of 4.6 out of 5 from guests
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.

Water Cistern • Mid-Century Modern House
No need to worry about unexpected water outages, the house has an automatic water cistern that keeps the water running if service is interrupted. 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.
4.9 out of 5 average rating, 125 reviews
Ocean Park Beachfront & Pool | 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.
4.99 out of 5 average rating, 150 reviews
Old San Juan Gem | Backup Power/Water, Pool + Pkg
Enjoy added peace of mind with solar power, battery backup, a private water cistern, and fiber internet, amenities rarely found in Old San Juan. Stay in a 200-year-old historic home in the heart of Old San Juan, complete with a heated private pool and dedicated parking just steps away. This spacious two-story retreat blends historic architecture, curated Puerto Rican art, and modern comfort, all within walking distance of the city’s best restaurants, shops, and landmarks.
4.99 out of 5 average rating, 101 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).
4.89 out of 5 average rating, 163 reviews
Centric Paradise Villa | Pool | Cruise ports
WATER & POWER BACKUP — Property equipped with water cistern and backup systems. Our guests are not currently affected by scheduled water rationing. Welcome to our inviting accommodations. Details below. Reach out with any inquiries. This is our spacious suite with a King-size bed and fully equipped kitchenette. Next to Paseo Caribe and Caribe Hilton, dine at nearby restaurants just a 5-min walk away. Between Old San Juan and Condado, experience the heart of the action.
4.84 out of 5 average rating, 108 reviews
Rare Beachfront Getaway w Pool, Gym, + Balcony!
Ocean Park Beach is right at your doorstep. Every color and detail in this studio apartment is inspired by the mesmerizing sunsets of Puerto Rico, offering a stay that's as visually stunning as it is comfortable. Wake up each morning in a bedroom where the view of the ocean from your bed is as stunning as the sunrise colors in the sky. Your balcony is the perfect romantic backdrop for a tranquil morning coffee or an enchanting evening under the stars.
4.92 out of 5 average rating, 145 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.
4.99 out of 5 average rating, 297 reviews
Sunrises Near Beaches+Power+Private Balcony
WATER & POWER BACKUP — Property equipped with water cistern and backup systems. Our guests are not currently affected by scheduled water rationing. Welcome to our property, a contemporary haven that lives up to its name. Situated on the 5th floor of the Condado Lagoon Villas I, this east-facing condominium is an integral part of the opulent high-end complex that houses the renowned Caribe Hilton Hotel and the stylish award winning Paseo Caribe.
4.8 out of 5 average rating, 110 reviews
⭐️SPECTACULAR CHIC STUDIO PROFESSIONALLY SANITIZED⭐️
Stay in the heart of Condado and enjoy beautiful ocean views by day and sparkling city views at night. 🌊🌆 This stylish 19th-floor apartment is surrounded by some of San Juan’s best restaurants, hotels, casinos, beaches and shops, all within walking distance. Located just about 10 minutes from SJU Airport and a short ride from Old San Juan, it’s an ideal home base for enjoying everything the city has to offer. ☀️🇵🇷
4.94 out of 5 average rating, 547 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.
4.88 out of 5 average rating, 138 reviews
Ocean & City View Studio in Condado, San Juan
Studio with ocean and city views in the heart of Condado, steps from the beach, restaurants, shops, casinos and nightlife. Building amenities include pool, tennis court, gym, game room, reading room, laundry room, lobby market and 24/7 security. Water during rationing: Building reserve system maintains water service during scheduled interruptions.
4.82 out of 5 average rating, 131 reviews
Villa Estrella PR (near Airport & Beach)
Have fun with the whole family at this stylish place. It's close to all the essentials such as the Airport and Beaches (5 minutes), Old San Juan, Plaza Las Américas (15 minutes). Located near several prestigious restaurants such as Bebo's BBQ, Metropol, and the Piñones tourist area where you can find typical food from our island.
4.98 out of 5 average rating, 239 reviewsPopular amenities for Viejo San Juan rentals with a pool
House rentals with a pool

Steps to Beach, 3BR/3BA, Own Pool, Parking, Gen
4.9 out of 5 average rating, 290 reviews
The Leaves Apartments #2
4.86 out of 5 average rating, 175 reviews
Lake Villa House in Toa Baja, Puerto Rico
4.97 out of 5 average rating, 126 reviews
Villa Celestial Luxury Home
4.99 out of 5 average rating, 136 reviews
Casa Aurea - Cozy House in the Metro Center Area
4.96 out of 5 average rating, 102 reviews
Casa Hélice 3 min from airport -Placas Solares-
4.94 out of 5 average rating, 113 reviews
Casa Reyes
4.99 out of 5 average rating, 144 reviews
Private Pool•Power/Water Backup•Near Airport•Gated
4.93 out of 5 average rating, 137 reviewsCondo rentals with a pool

★Luxurious Beachfront Apt in Isla Verde+free pkg★
4.92 out of 5 average rating, 423 reviews
Amazing Ocean-View / Condado Beach/ Pool
4.91 out of 5 average rating, 202 reviews
San Juan-Condado Ashford Ave. Best Studio!
4.91 out of 5 average rating, 226 reviews
Condado Beach Vistas… Elevate Your Stay!
4.9 out of 5 average rating, 303 reviews
Ocean View - Prime Location - Parking - ORO SUITE
4.88 out of 5 average rating, 327 reviews
Deja Blue BeachFront Apartment @ Isla Verde (Green Island)
4.96 out of 5 average rating, 158 reviews
Modern & Stylish studio, steps to beach, Generator
4.82 out of 5 average rating, 186 reviews
Isla Verde Beachfront Studio near restaurants,bars
4.95 out of 5 average rating, 194 reviewsOther holiday rentals with a pool

Direct beach access... best spot in Condado
4.91 out of 5 average rating, 447 reviews
Red Door Lovely 1 Bedroom unit with small patio
4.94 out of 5 average rating, 156 reviews
Isla Verde • Modern Oceanfront • Prime Location
4.9 out of 5 average rating, 102 reviews
Ashford Imperial Condo- Oceanview and Parking
4.92 out of 5 average rating, 172 reviews
King Bed Loft | by Old SJ & Escambrón Beach | Pool
4.93 out of 5 average rating, 136 reviews
Beautiful Retreat w. Pool and Perfect Location
4.94 out of 5 average rating, 136 reviews
Contemporary Condado Beach Studio with Ocean View
4.98 out of 5 average rating, 318 reviews
Ocean front with city view Condado del Mar
4.89 out of 5 average rating, 233 reviewsWhen is the best time to visit Viejo San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $589 NZD | $727 NZD | $729 NZD | $586 NZD | $538 NZD | $483 NZD | $462 NZD | $572 NZD | $462 NZD | $336 NZD | $423 NZD | $523 NZD |
| Avg. temp | 25°C | 25°C | 26°C | 27°C | 28°C | 28°C | 28°C | 29°C | 29°C | 28°C | 27°C | 26°C |
Destinations to explore
- Condo rentals Viejo San Juan
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- Apartment rentals Viejo San Juan
- Rentals with a hot tub Viejo San Juan
- Waterfront rentals Viejo San Juan
- Rentals with beach access Viejo San Juan
- Pet-friendly rentals Viejo San Juan
- Rentals with pools San Juan Region
- Rentals with pools Puerto Rico
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Puerto Rico Convention Center
- Distrito T-Mobile
- Rio Mar Village
- Playa Puerto Nuevo
- José Miguel Agrelot Coliseum
- La Pared Beach
- Cond Marbella del Caribe Este
- Playa de Luquillo
- Plaza Las Americas
- Punta Bandera Luquillo PR
- San Patricio Plaza
- Isla Verde Beach West
- Los Tubos Beach
- Cueva del Indio
- La Guancha
- Isla Palomino
- Museo de Arte de Puerto Rico
- Hacienda Campo Rico
- Balneario de Luquillo
- Cond Ashford Imperial
- Cond Marina Lanais





