
Holiday rentals with a pool in Roosevelt Roads
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Roosevelt Roads
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House
Our 2025 Puerto Rico vacation was so enjoyable!!! The home was perfect just a describe and the pictures that are shown in the listing. The house is beautiful, private, and in a safe neighborhood. The backyard is perfect to relax, cook out and enjoy family time. The home truly came with everything you need for a beach vacation!! All you need to pack is your clothes. Already planning to book at the house again for our family 2026 Puerto Rico vacation. Luis is an amazing host!!

Villa Estrella PR (near Airport & Beach)
We had a terrific stay in this beautiful home. Everything was so convenient and the pool was very relaxing! We would definitely recommend this home to anyone and would love to come back and visit again sometime!

Renald's Place
We stayed for a week and this has been the most wonderful and amazing Airbnb we have ever booked! The local beaches and “kiosks” were amazing. Our kids enjoyed everything about our vacation. Renald’s place came equipped with life jackets, beach toys, beach umbrellas, and chairs. The home overall was clean and everything was as described. This was our first time visiting Puerto Rico and we hope to be back soon. Thank you Renald, Maria, and Nicole. - The Q Family

Beautiful House, 24/7 Security, Gated Community
La estadía en la casa de Alexander fue genial. La casa grande y espaciosa con una hermosa decoración para nuestro grupo de 8 personas fue perfecta y excelente con todas las comodidades necesarias. La casa es tal y como muestran en las fotos. La comunicación fue excelente, muy receptiva y nos atendió muy al igual que contestó rápidamente todas las preguntas realizadas. El área de la piscina y el jacuzzi en el patio un toque refrescante y hermoso para disfrutar en grupo o en familia. Un lugar muy encantador que te invita a quedarte en él nuevamente en un futuro.

Lake and Beach Village, Humacao
It was an amazing stay, my family and I enjoyed it. Nelson was a very great host, would definitely recommend him to my family and friends. I would also be going back for another stay. My mission for my husband to reunite him with his dad was a successful mission all thanks to Nelson.

The Leaves Apartments #2
Zulmarie’s home was extremely comfortable! We felt extremely safe! She always responded right away! The house was beautiful! We had an amazing time!

Casita Domirriqueña
Toda una experiencia relajante, muy limpio, lugar tranquilo y la casa contiene todo lo que puedas necesitar para la estadía. Lo recomiendo al 100%. Los anfitriones muy atentos y responden rápido. Estábamos celebrando el cumpleaños de mi hijo y Sandy decoró el cuarto con globos tal como lo solicité. Superaron mis expectativas. Gracias.

❤️PRIVATE POOL,Beach home,BioBay Tour walk distance
Al’s place was great in a great area close to local attractions. The pool made it nice to relax on days that you would like to relax. Plenty of restaurants with in walking distance of the house. Quiet neighborhood that we felt safe walking through.
Apartment rentals with a pool

Estudio al Mar
Great location in the heart of town. Grateful for the beach essentials to elevate any experience. Would highly recommend and stay again.

Ocean View/Mountain Setting 3 - Owners Suite
our stay was absolutely amazing. The place looks exactly like the pictures – the views are stunning, the pool and jacuzzi are perfect for relaxing, and the whole vibe is just so peaceful and comfortable. Our host (Tom) was incredibly welcoming, kind, and always available to answer any questions or offer recommendations (he literally has a binder with food recommendations, beaches and activities). You can really tell tom cares about making sure guests have a great experience. The location is fantastic, with easy access to everything you want to see in Puerto Rico, and the property itself is like a little slice of paradise. If you're looking for a relaxing getaway with all the amenities and more, this is definitely the spot! Highly recommend this place, and I can’t wait to come back!

New! Breath Taking View at Las Casitas Village
we loved our stay here! the highlights: 2 big bedrooms, lots of living space, & a great view for coffee each morning on the balcony! We arrived very late, but the host made sure we knew exactly where to go & what to do. Thanks for a fantastic stay!

*Azul Marino* Golf & Ocean View Luxury Condo
Wonderful experience. Resort is amazing. Landscaping perfection and staff is very friends. Units was clean comfortable and as described. View is breath taking. Will come back !

Waterfront High-Rise Apt with Gorgeous Ocean View
Amy made access incredibly easy, the condo was well guarded and we felt safe. The views are beautiful, just a great condo where you will fall asleep to the sounds of the waves and the coqui. Amy has a closet filled with things you may need for a beach day which was perfect and a well equippped kitchen.

Breathtaking Ocean View Apartment
This airbnb is exceptional. It has above and beyond amenities/stock like tin foil, sunscreen, beach towels, umbrella, beach game. Additionally- the views are wonderful, the ac works and the bed is comfy! Literally my only note for the whole place is that the pillows are intensely stuffed and for someone with neck problems this posed a difficulty for me- this is minor, but just wanted to note it. I hope to stay here again! I read reviews that said grocery store, etc was walkable and while this is true- I thought it would be helpful to know that the grocery and walgreens are across a pretty busy highway like road- so we drove even though it is right across the street. Luquillo which is walkable (by beach or street) or a short drive had restaurants, coffeeshops, breakfast, etc.

Panoramic Ocean View - Encanto del Mar
Encanto del mar is an excellent apartment to stay. Clean and beautiful place to stay. Joe & Jessica excellent hosts. Hope to come back in the future.

Fajardo PR Modern Oceanfront Condo Million $ Views
Sara and Alex are great hosts and I highly recommend their “Encanto” apartment. So beautiful and I would absolutely come back!
Quick stats about holiday rentals with a pool in Roosevelt Roads
Total rentals
90 properties
Nightly prices starting at
₹3,455 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Rio Mar Village
- Distrito T-Mobile
- Playa del Dorado
- Praia de Luquillo
- Liquillo Beach
- Playa Sun Bay
- Playa el Convento
- Beach Planes
- Coco Beach Golf Club
- Playa Puerto Real
- Hull Bay Beach
- Toro Verde Adventure Park
- Carabali Rainforest Park
- Playa Maunabo
- The Saint Regis Bahia Golf Course
- Mandahl Bay Beach
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- Playa de Cerro Gordo
- Morningstar Beach