
Vacation 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 family loved our time at Luis & Ivette's place during our family vacation. Luis reached out to us on day one to ensure we had a smooth check-in, offer suggestions for local restaurants and activities and introduce us to the neighborhood. The home was lovely and well-equipped. The outdoor space is fantastic for relaxing, grilling, and playing with children. Our granddaughter swam in the pool every day and we really appreciated all the games and pool toys that were available for her use. A wonderful place to stay with plenty of room for families.

Casa Blanca with pool, tropical garden and rooftop
One of our best airbnb stays so far, the house was fantastic and the hosts were amazing. We spent 8 days here and would spend weeks more if possible. Highly recommend.

Home for 9 with Pool and Solar Panels in Vieques!
Beautiful place and wonderful host!

Beautiful House, 24/7 Security, Gated Community
The house was exactly as picture. It’s a beautiful home, and I would definitely recommend.

Coastal Getaway with Pool, Game Room & Ocean View
Wonderful stay, beautiful place, can’t ask for anything more

We are back! Puerto Rican paradise awaits you!
Rick is a superior host, kind and communicative! The house was everything we could wish for. Steps to a beautiful beach, and a private pool, gorgeous views! Just perfect!

Casa Amor Home Esperanza Salt Pool- close to Beach
Our stay in Vieques was absolutely wonderful. The house was beautiful, peaceful, and so relaxing — we especially loved the fruit trees, and our son spent hours happily splashing in the pool. When a power outage affected the whole island on our first day, Janos went out of his way to bring us a power bank for our phones and ice for our groceries. Throughout the trip, he checked in to make sure we were comfortable and had everything we needed. When our son accidentally left his favorite stuffed animal behind, they even kindly mailed it back to us — something we’ll always be grateful for. We truly felt so cared for during our stay. It was hard to leave, and we’re already dreaming about coming back!

Family Escape Resort Private Pool Near the Beach
Our li'l fam very much enjoyed our stay at Jonathan and Monica's cozy and relaxing place because it was exactly what we were looking for. Instead of being cooped up in a small hotel room with a possible pool many floors away, everything we needed was right there. Rainforest hikes, beautiful beaches, local restaurants, city sightseeing, and more all short drives away, but we were perfectly happy hanging at their place without too busy of an agenda. This would be a great place not just for a family, but a group of friends as well. We highly recommend staying here as it was a big factor for such a fun, relaxing vacation.
Condo rentals with a pool

Lovely Caribbean Oasis Condo with pool/gym
We loved staying in this apartment. Very comfortable, accessible and clean. Stephanie & Wesley are excellent hosts and maintained excellent communication with us. 100% recommended✨

Relax in modern ocean condo with amazing 270° view
Second time we have stayed at this incredible place. The wind, the ocean, the rainforest- it is so beautiful. The condo is comfortable and AC in the bedrooms works great. We swam in the ocean and also enjoyed the pool at the condo! We love this place.

Ocean View Penthouse Condo with A/C in every Room
Excellent location, very quiet place, very comfortable for the family and for kids, beautiful view, beautiful surroundings, with a beach, a pool, a basketball and tennis court, too and a 10 minute walking distance from the "Malecón de Naguabo" where there are a lot of places to eat and very delicious. Hosts very responsive and proactive to help with everything! Thanks Diane and Luis for sharing this blessed place with us!

Lovely Ocean View Apartment
This unit is exactly as pictured with plenty of space, comfy beds and linens, a stocked kitchen and beautiful view. Cold AC in both bedrooms, but not in the living room. Secure building with elevators. Slightly dated but clean and well kept. Our only complaint was the location is next to a very busy marina, there is often noise and loud music from the boats and the restaurant next door but it stopped by midnight or so. Overall we were very pleased and would definitely stay here again!

Casa Family 3 bedroom condo with pool & gated area
Vincent went out of his way to help us with recommendations and even brought over some books for us to read. He was flexible and kind and we very much appreciated his help as well as his very capable staff. Someone met us at the Amigo supermarket and led us to the condo. They were all great.

Perfect Location 3bd2ba CondoVacation/Business
Brad & Juanita condo was just right bed was conftoble water pressure was good The location was perfect, with many beaches nearby and We enjoyed exploring the area and found plenty of great dining options nearby. , our experience was amazing. We would highly recommend

Remodeled H402 Beach Access Ocean View Penthouse
We were glad to book this place with Fredy and Suany. Got there at 4 pm, the place was ready on time. Very private, clean, spacious place with breathtaking views of mountains and ocean. The lockboxes are mounted on the parking lot concrete blocks!! There are 2 parking spots for this apartment-and they are not close by!! There is a private beach for the complex that is quiet. Please read the beach conditions for Puerto Rico. Stores close by, also large supermarkets in 7 miles. Don’t forget to get a Pizza takeout from D&D pizza nearby-thin crust (fine crust) with Pepperoni, pineapple and jalapeño :). Check out local bakeries (La Familia) for breakfast fun! Close to both San Juan or tropical forest hiking!!

Beachfront Top Floor Condo next to Wyndham Hotel
This was our second time staying here and we loved it again! It fits our family of four so nicely. We can easily make meals and hang out on the balcony looking at the beautiful ocean or walk down and be right on the beach in minutes. We even reached out once to Tom noticing something was missing from the kitchen and he went to the store and brought it to us the very next day. Totally not expected and way above and beyond! We hope to come back next year and would definitely stay again if it is available.
Quick stats about vacation rentals with a pool in Roosevelt Roads
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ147 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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- Limetree Beach
- Distrito T-Mobile
- Morningstar Beach
- Carabali Rainforest Park
- Punta Bandera Luquillo PR
- Hull Bay Beach
- Mandahl Bay Beach
- Playa Maunabo
- Playa Puerto Real
- Coco Beach Golf Club
- Playa de Cerro Gordo
- Toro Verde Adventure Park
- Inches Beach
- Playa Media Luna
- Luis Pena Beach
- The Saint Regis Bahia Golf Course
- Playa Vacia Talega
- La Fortaleza
- Playa de los Cabes
- Playa Mala Pascua
- Vessel
- Punta Guilarte Beach
- Sun Bay Beach
- Playa Larga