
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.

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

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!

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.

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.

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.

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)

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

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.

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.

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.

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!

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
House rentals with a pool

Super comfortable Family Home w/ private pool

Villa Tropical Piscina privada Wifi y Neflix

Casa Reyes

Casa Minnelli,5 minutes from the airport and beach

La Pompa Beach House Beautiful Residence with Pool

Hidden Coast

Luxury Casa Caliad

Private Pool•Near Airport•Solar System•Gated Area
Apartment rentals with a pool

Ashford Imperial/New, modern, beach condo/King bed

Deja Blue BeachFront Apartment @ Isla Verde (Green Island)

Rare Beachfront Getaway w Pool, Gym, + Balcony!

Ashford Imperial. Best Location.

Studio in the heart of Condado

Luxury Junior Suite

Isla Verde Beachfront Studio near restaurants,bars

Beautiful apartment in Condado with beach access!
Other holiday rentals with a pool

Guaynabo, Private pool, billiard room.

Boho Tropical Oasis | 3 BR+Pool

Beachfront Ocean Park | Sleeps 8 | Pool + 1Parking

Tropical Escape: 4BR House w/ Pool Near the beach!

"San Juan Escape at Solemare"

Casita Hydra • Private Pool • Near Airport & Beach

Japandi Loft-Private Pool & Outdoor Shower | Osaka

Historic Old San Juan Home | Heated Pool + Parking
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 | $430 SGD | $531 SGD | $532 SGD | $550 SGD | $356 SGD | $296 SGD | $337 SGD | $418 SGD | $337 SGD | $245 SGD | $309 SGD | $382 SGD |
| 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 |
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
Destinations to explore
- Flat rentals Viejo San Juan
- Waterfront rentals Viejo San Juan
- Hotel rooms Viejo San Juan
- Rentals with beach access Viejo San Juan
- Family-friendly rentals Viejo San Juan
- Fitness-friendly rentals Viejo San Juan
- House rentals Viejo San Juan
- Rentals with a washing machine and dryer Viejo San Juan
- Rentals with a patio Viejo San Juan
- Rentals with a hot tub Viejo San Juan
- Boutique hotels Viejo San Juan
- Apartment rentals Viejo San Juan
- Smoking-friendly rentals Viejo San Juan
- Pet-friendly rentals Viejo San Juan
- Rentals with outdoor seating Viejo San Juan
- Rentals with pools San Juan Region
- Rentals with pools Puerto Rico
- Isla Verde Beach West
- Liquillo Beach
- Puerto Rico Convention Center
- Distrito T-Mobile
- Playa las Picuas, Rio Grande
- José Miguel Agrelot Coliseum
- El Yunque National Forest
- Rio Mar Village
- Playa de Luquillo
- La Pared Beach
- Toro Verde Adventure Park
- Carabali Rainforest Park
- Playa Puerto Nuevo
- Cond Marbella del Caribe Este
- Punta Bandera Luquillo PR
- Los Tubos Beach
- Plaza Las Americas
- San Patricio Plaza
- Museo de Arte de Ponce
- Cueva del Indio
- Museo de Arte de Puerto Rico
- Balneario de Luquillo
- Playa puerto nuevo
- Hacienda Campo Rico
- Things to do Viejo San Juan
- Things to do San Juan Region
- Sightseeing San Juan Region
- Food and drink San Juan Region
- Tours San Juan Region
- Sports activities San Juan Region
- Art and culture San Juan Region
- Nature and outdoors San Juan Region
- Entertainment San Juan Region
- Things to do Puerto Rico
- Entertainment Puerto Rico
- Sports activities Puerto Rico
- Food and drink Puerto Rico
- Nature and outdoors Puerto Rico
- Tours Puerto Rico
- Art and culture Puerto Rico
- Sightseeing Puerto Rico





