
Holiday rentals with a pool in San Juan
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in San Juan

Total holiday rentals
Explore 2,010 holiday rentals in San Juan

Nightly prices starting at
San Juan holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 150,600 verified reviews to help you choose

Family-friendly holiday rentals
870 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 470 rentals that welcome pets

Rentals with dedicated workspaces
1,150 properties have a dedicated workspace

Wifi availability
1,990 of San Juan holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across San Juan rentals

4.8 Average rating
San Juan stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
San Juan’s top spots include Distrito T-Mobile, Paseo de la Princesa and Museo de Arte de Puerto Rico
Top-rated rentals with a pool in San Juan
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Pineapple Suite 1BR | Pool + SunDeck | Ocean Park
Our Pineapple Suite is a 1-BR apartment with a private entrance located on the ground floor tucked behind our lush tropical garden as part of our exclusive multi-unit property that we call Beach Hous! We are located between two amazing beaches, both less than a two minute walk from Beach Hous! This apartment has a queen size bedroom with a private ensuite bathroom and views of the pool. The property has an automatic full-power backup generator and two cisterns. Max occupancy is 3 guests.

Magical! Ocean view Cabana w/ Pool Spa on mountain
This memorable place is anything but ordinary. You will get to enjoy this amazing and super private space surrounded by nature and unbelievable views of the ocean and the city. Fully equipped with everything you will need during your stay to include kitchen, full bath with rain shower, A/C, living space with 55" TV, dinning and sleeping areas, terrace with killer views, and of course the pool spa with infinity view! And many more. All of this while enjoying of a complementary bottle of Wine!

Condado, Walk to the Beach, on Ashford Avenue
Located in the heart of Condado, San Juan directly on Ashford Avenue! This condo is in one of the liveliest and most tourist-friendly areas of the entire island! It’s filled with bars, restaurants, casinos, shopping, and amazing beaches. And the beach is steps away! Located across from the San Juan Marriott Resort and Stellaris Casino. The condominium has amenities including a pool, a small gym, and a laundromat. Security 24/7. 10-15 minute taxi/Uber ride from San Juan’s airport (SJU).

Vista Linda Haus
At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

Private Rainforest Retreat ~10 min to Playa Azul~
Visiting El Yunque & Bio Bay? 🌺 Koko Kai Cabana is the perfect retreat - right between Luquillo and Fajardo - for exploring the Best of the East Coast 🇵🇷... You'll enjoy quiet, country life in the mountains of Juan Martin. But just 15 mins to Luquillo Beach, 20 to El Yunque or Bio Bay & shopping in Fajardo is only 7 mins down the mountain. We live on site, but the cabana is on the "3rd level" above the pool. It's private and tranquil... and everything is just for you two!

Wake Up to Ocean Views | Pool + Marina Paradise
A tranquil getaway in this stunning apartment with breathtaking ocean views. Step inside to discover modern updates & stylish design. The exclusive 2 suites feature beautiful windows, offering unobstructed view Unwind by the giant pool or enjoy the sunrise from the expansive balcony—perfect spots for relaxation. The fully equipped kitchen with exotic white granite countertops is ideal for whipping up meals. This is the perfect retreat for those seeking luxury & serenity!

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.

Sunrises Near Beaches+Power+Private Balcony
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. This exquisite space offers a single king-sized bed, a fully equipped kitchen and breathtaking vistas. Embark on your Puerto Rican escapade right here.

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).

Villa Estrella PR (near Airport & Beach)
Diviértete con toda la familia en este alojamiento con estilo. Esta cerca de todo lo esencial como el Aeropuerto y Playas (5 minutos), Viejo San Juan, Plaza Las Américas (15 minutos). Localizado cerca de varios restaurantes con prestigio como Bebo’s BBQ, Metropol, y el área turística de Piñones donde podrán encontrar comida típica de nuestra isla.
Popular amenities for San Juan rentals with a pool
House rentals with a pool

Black House

Private Pool•Near Airport•Solar System•Gated Area

Luxury Beach House with Private Pool in Condado

Lake Villa House in Toa Baja, Puerto Rico

Luxury Kiarita House • Hill House

Hacienda Azucena, Río Grande, Yunque Rainforest

The Coral · Isla Verde · Pool 4BR Gated Community

Casa Hélice 3 min from airport -Placas Solares-
Apartment rentals with a pool

Deja Blue BeachFront Apartment @ Isla Verde (Green Island)

San Juan-Condado Ashford Ave. Best Studio!

Isla Verde Studio @ St. Tropez, Steps to the Beach

Isla Verde Beachfront Studio near restaurants,bars

Lux BEACH FRONT 19th Floor 1BR w/Pool & PK

Condado - Ashford Imperial - Epic ocean views

💙BLUE DREAM OCEANFRONT W/ VIEW AT ISLA VERDE 2BR

Condado Del Mar Suite 1110"
Other holiday rentals with a pool

"Stellita Glamping"

King Suite Steps from the Beach w/ Parking

⭐️SPECTACULAR CHIC STUDIO PROFESSIONALLY SANITIZED⭐️

Beach Vacay!

Tierra Linda TreeHouse Private Pool & River

Villa Vista Hermosa, Río Grande, Puerto Rico

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

Ashford Imperial Condo- Oceanview and Parking
When is the best time to visit San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £144 | £146 | £152 | £136 | £130 | £128 | £131 | £133 | £123 | £115 | £126 | £136 |
| 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 |
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- Flamenco Beach
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Distrito T-Mobile
- Puerto Rico Convention Center
- Rio Mar Village
- Playa Puerto Nuevo
- José Miguel Agrelot Coliseum
- Playa de Luquillo
- La Pared Beach
- Carabali Rainforest Park
- Toro Verde Adventure Park
- Cond Marbella del Caribe Este
- Punta Bandera Luquillo PR
- Plaza Las Americas
- Los Tubos Beach
- Isla Verde Beach West
- San Patricio Plaza
- Cueva del Indio
- Museo de Arte de Ponce
- Sun Bay Beach
- Museo de Arte de Puerto Rico
- Playa puerto nuevo
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