
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 $222 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.

Casa Reyes
Welcome to Casa Reyes! A spacious and relaxing family home fully renovated and redesigned to meet our guests’ vacation needs. Casa Reyes offers all the amenities for you and your family to relax on your stay. Located in one of San Juan’s most vibrant neighborhoods, Ocean Park, Casa Reyes is in between the tourist areas of Condado and Isla Verde. It’s walking distance to the beach, fine dining restaurants, clubs, nightlife, and many tourist attractions making it perfect for your vacation stay.

Romantic Oceanfront Private Patio Full Generator
** WE ARE NOT AFFECTED BY WATER DROUGHT OR POWER OUTAGES** Villa has power generator that covers the full inside plus an extra large water cistern 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 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.

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.

Isla Verde • Modern Oceanfront • Prime Location
Enjoy oceanfront living in Isla Verde from your 17th-floor apartment, featuring stunning lagoon and city skyline views. Just an elevator ride from the beach, this stylish getaway is steps from top restaurants 🥂, lively nightlife 🎶, and all the coastal charm the area is known for. Designed for a seamless stay, it offers high-speed WiFi, private parking 🅿️, backup power ⚡️, and thoughtful details throughout—ideal for couples or small families looking for comfort and convenience.

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.

Dream Retreat 2br 2bth + Ocean View + 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).

Epic Ocean View, 23 floor, Balcony & Free Wi-fi
The unit is conveniently located on Ashford Avenue in the fashionable Condado district of San Juan, one of Puerto Rico's most popular beachfront destinations. Known for its beautiful beaches, vibrant nightlife, and lively atmosphere, Condado offers the perfect blend of relaxation and entertainment Whether you choose to explore the island or simply relax by the ocean, this location provides the perfect balance of convenience, comfort, and authentic Puerto Rican charm.

Luxury waterfront villa with dock and heated pool
Enjoy uninterrupted water and power at Villa Jade, with a whole-house generator and 600-gallon water cistern for peace of mind. Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock on a serene lagoon. Just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

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.

Casa Arena | Elegant Ocean Views
*** Bookings in September will not have balcony access due to building maintenance. *** Casa Arena is our second property on Airbnb and our latest family endeavor. It has been thoughtfully designed for travelers seeking an upscale studio during their visit to Puerto Rico. We offer a king-sized bed, a stocked kitchen and spacious balcony for you to relax, enjoy the breeze and take in the stunning views.

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).

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.
Popular amenities for Viejo San Juan rentals with a pool
House rentals with a pool

Casa Hélice 3 min from airport -Placas Solares-

Villa Celestial Luxury Home

Casa Ocean PR

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

Hidden Coast

Lake Villa House in Toa Baja, Puerto Rico

Case Del Sole Duplex w/ Solar-Powered Backup

Casa Kenia
Condo rentals with a pool

Beachfront & Pool at the Best Location in Condado

BLUE DREAM Oceanfront W/ VIEW AT Isla VERDE 2BR

Isla Verde Beachfront Studio near restaurants,bars

Condado Beach Views by Cesar 2501

Ocean & City View Studio in Condado, San Juan

★Luxurious Beachfront Apt in Isla Verde+free pkg★

Ashford Imperial. Best Location. We have water

Beach Front
Other holiday rentals with a pool

Modern Studio, Spectacular View, Parking On Site

Ashford Imperial Condo- Oceanview and Parking

Lovely 1 bedroom apartment with private terrace

Best location with pool, steps from beach!

Beach Vacay!

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

2Lvl CityView Penthouse on Beach, Rennovated 2022

Sunrises Near Beaches+Power+Private Balcony
When is the best time to visit Viejo San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $577 NZD | $712 NZD | $714 NZD | $573 NZD | $527 NZD | $472 NZD | $452 NZD | $560 NZD | $452 NZD | $329 NZD | $414 NZD | $512 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
- Family-friendly rentals Viejo San Juan
- House rentals Viejo San Juan
- Hotel rooms Viejo San Juan
- Boutique hotels Viejo San Juan
- Apartment rentals Viejo San Juan
- Rentals with a hot tub Viejo San Juan
- Rentals with beach access Viejo San Juan
- Waterfront rentals 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
- La Pared Beach
- José Miguel Agrelot Coliseum
- Cond Marbella del Caribe Este
- Playa de Luquillo
- Punta Bandera Luquillo PR
- Plaza Las Americas
- San Patricio Plaza
- Isla Verde Beach West
- Los Tubos Beach
- Cueva del Indio
- La Guancha
- Isla Palomino
- Museo de Arte de Puerto Rico
- Balneario de Luquillo
- Cond Ashford Imperial
- Hacienda Campo Rico
- Cond Marina Lanais





