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Holiday rentals with a pool in San Juan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Juan

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

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Rental unit in San Juan

4.82 out of 5 average rating, 215 reviews

Beach-A-Holic Paradise @ Condado- Steps from Beach

Studio Apt with breathtaking water views, beach access, and sleeping space in the living room, perfect for couples with children. Located on trendy Ashford Ave. with cafes, restaurants, shops, and parks. Condo has 24/7 gated security, a gym, tennis courts, game room, pool, and free on-site parking. Please note that our property is in a charming, yet older building in a great neighborhood. The administration is actively working on improvements, including a full generator expected by Winter 2025.

Guest favourite

Tiny home in Río Grande

5 out of 5 average rating, 368 reviews

El Yunque Rainforest Tiny House

La Cuchin is a Tiny House inspired by the old houses in the Countryside of PR with some of the comforts of today, like AC And WiFi Special touches throughout the Cabin make your stay more special. Nestled among the mountains of the Rainforest, at night you will hear the sounds of the Coqui and crickets and if you are lucky, the rain over the Tin Roof. Our Outdoor Garden Tub is a place where you will leave all of your worries behind! The Pool in the main house is also available to the Guests.

Guest favourite

Rental unit in Levittown

4.88 out of 5 average rating, 112 reviews

Happy House - Family friendly with private pool

Children are welcomed with open arms in this cheerful, bright and well-kept Levittown apartment. Expect a space complete with amenities parents know can make or break a family vacation. Toys, books, board games, dinnerware, a stroller and more. In the backyard, you will find a terrace furnished with a sectional perfect to watch the kids while they use the playground and an outdoor dinning set. Pharmacies, gas stations and supermarkets walking distance. The nearest beach is 5 minutes away.

Condo in San Juan

4.85 out of 5 average rating, 295 reviews

Beautiful apartment in Condado with beach access!

Beautiful studio apartment. Includes one queen and one twin Murphy bed. Also has washer/dryer in the apt. Condo has a pool, gym, tennis court, mini market and private access to the beach. The studio can be converted as two rooms with a door divider. The view from the sliding windows is to the city. Only one parking available with security. Great spot within walking distance of bars, restaurants, supermarket, and ATMs. Feel free to contact me for any questions.

Guest favourite

Condo in San Juan

4.93 out of 5 average rating, 169 reviews

San Juan-Condado Ashford Ave. Best Studio!

We want you to feel like your home! Just remodeled studio-apartment with ocean view. This new and modern open loft studio has all the hotel amenities you need, including: pool, jacuzzi, gym and 24/7 security. It is located in the heart of Condado, San Juan’s main tourist district. The most dynamic, trendy and multicultural city area, close to the spectacular historic Old San Juan City. Nearby restaurants, markets and just a block away from the beach.

Guest favourite

Rental unit in San Juan

4.99 out of 5 average rating, 222 reviews

Best location with pool, steps from beach!

Wake up on your super comfortable king premium bedding looking over a beautiful pool surrounded with gorgeous palm trees. Surprise your significant other preparing her/his breakfast choice in your fully equipped kitchen, get up to date with a super-fast internet connection under your secluded patio roofed pergola. Dive in your private pool, get a hot water outdoor shower before heading to the best beach of San Juan, just 50 yards from your house!

Guest favourite

Condo in San Juan

4.89 out of 5 average rating, 137 reviews

Condado - Ashford Imperial - Epic ocean views

The Condo is located on the 22nd floor and has one of the best ocean views in Condado. Amenities include a comfortable studio apartment with amenities to cook, a beautiful lounge area, large pool and reading room. Hi speed WiFi and cable are also included. We are located directly on the main strip within walking distance to all stores and restaurants including Starbucks, Walgreens and an organic foods market.

Guest favourite

Condo in San Juan

4.9 out of 5 average rating, 230 reviews

Condado Beach Vistas by Cesar 2501

Immerse yourself in our cozy studio, with mesmerizing ocean and city views plus the calming sea sounds of Condado Beach. Our secure building offers 24/7 security, a doorman, and reserved parking. Steps away from the beach, trendy shops, and delicious dining, our condo blends urban excitement with beachside tranquility. Enjoy the magical city lights from our balcony, inviting you to cherish every moment.

Guest favourite

Rental unit in Condado

4.92 out of 5 average rating, 352 reviews

Casa Lola | Trendy Oceanview Studio

Casa Lola was our first property on Airbnb and the one we hold dearest. It has been thoughtfully designed for travelers looking for a trendy homebase during their visit to Puerto Rico. We offer a queen-sized bed, a stocked kitchen and spacious balcony for you to relax, enjoy the breeze and take in the stunning views. Oh and most importantly, the Airbnb is named after my lovely puppy, Lola.

Guest favourite

Rental unit in San Juan

4.89 out of 5 average rating, 155 reviews

Vacation mode: La Rada 220!

Location, Location, Location!! Enjoy your stay in La Rada 220 in this cozy, newly renovated studio apartment centrally located in the heart of Condado (San Juan, PR). This studio apartment with all the comforts and quickly access to all the most attractive places of the city like our historic Old San Juan. You’ll find a great variety of restaurants, cafes and shops at your doorsteps.

Guest favourite

Condo in San Juan

4.94 out of 5 average rating, 336 reviews

Ashford, San Juan -“The Place”!

The heart of New San Juan... Fall in love with Condado, San Juan’s most exciting district. Condado’s oceanfront, tree-lined community offers an array of elegant hotels, restaurants, boutiques, and more. Everything is within walking distance, including stunning beaches where you can dine at beachside restaurants, go paddle boarding or just relax in the sun.

Guest favourite

Loft in Fajardo

4.92 out of 5 average rating, 157 reviews

Marina Ocean View - The Bohemian Nest

Welcome to your own private bohemian paradise in Fajardo, Puerto Rico! This stunning studio apartment is the perfect blend of laid-back bohemian style and luxurious comfort, located on the 5th floor of a prestigious building with a marina and breathtaking ocean views.

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Popular amenities for San Juan rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in San Juan

4.9 out of 5 average rating, 188 reviews

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

Home in Cangrejo Arriba

4.85 out of 5 average rating, 155 reviews

»»VillaTrópico««Pvte.Pool 3mn Walk to Beach | 4BD

Guest favourite

Home in Levittown

4.94 out of 5 average rating, 102 reviews

La Pompa Beach House Beautiful Residence with Pool

Home in Luquillo

4.91 out of 5 average rating, 117 reviews

Renald's Place

Guest favourite

Home in San Juan

4.98 out of 5 average rating, 164 reviews

Urban Beach Hideaway...a luxury family compound!

Guest favourite

Home in San Juan

4.96 out of 5 average rating, 135 reviews

Costa Escondida

Guest favourite

Home in Trujillo Alto

4.93 out of 5 average rating, 160 reviews

Unique luxury house-Private pool-Power generator

Guest favourite

Home in Río Grande

4.91 out of 5 average rating, 138 reviews

Private Beachfront Home - Weather Guarantee*

Condo rentals with a pool

Guest favourite

Condo in San Juan

4.9 out of 5 average rating, 145 reviews

High Rise Ocean Waves In Condado

Guest favourite

Condo in Luquillo

4.89 out of 5 average rating, 277 reviews

Breathtaking Oceanfront and City View “Playa Luna”

Guest favourite

Condo in San Juan

4.99 out of 5 average rating, 101 reviews

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

Guest favourite

Condo in Cangrejo Arriba

4.95 out of 5 average rating, 119 reviews

Isla Verde Beachfront Studio near restaurants,bars

Guest favourite

Condo in San Juan

4.92 out of 5 average rating, 432 reviews

OCEAN VIEW/BEACHFRONT/CONDADO + POOL

Condo in Cangrejo Arriba

4.8 out of 5 average rating, 178 reviews

Isla Verde Charming Studio…

Condo in San Juan

4.82 out of 5 average rating, 114 reviews

Lovely studio in condo with pool at Josem’s Place

Guest favourite

Condo in Luquillo

4.93 out of 5 average rating, 238 reviews

Miles of Blue, THIS VIEW waiting for you!

Quick stats about holiday rentals with a pool in San Juan

Total rentals
1.9K properties
Nightly prices starting at
$30 AUD before taxes and fees
Total number of reviews
110K reviews
Family-friendly rentals
680 properties are a good fit for families
Pet-friendly rentals
370 properties allow pets
Rentals with dedicated workspaces
990 properties have a dedicated workspace

Destinations to explore