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Holiday rentals with a pool in Roosevelt Roads

Find and book unique homes with a pool on Airbnb

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Popular amenities for Roosevelt Roads rentals with a pool

House rentals with a pool

Top guest favourite
Home in Buena Vista
4.98 out of 5 average rating, 103 reviews

Amazing Infinity pool @Coqui Tropical House

VanessaRating, 5 stars1 month ago
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!!
Superhost
Home in Luquillo
4.91 out of 5 average rating, 143 reviews

Renald's Place

Ana LuisaRating, 5 stars3 weeks ago
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
Guest favourite
Home in Humacao
4.91 out of 5 average rating, 274 reviews

Beautiful House, 24/7 Security, Gated Community

AstridRating, 5 stars2 weeks ago
The stay at Alexander's house was great. The large and spacious house with a beautiful decoration for our group of 8 people was perfect and excellent with all the necessary amenities. The house is as shown in the photos. The communication was excellent, very responsive and we were attended to very well, as well as answering all the questions asked quickly. The pool area and the jacuzzi in the courtyard are a refreshing and beautiful touch to enjoy as a group or as a family. A very charming place that invites you to stay there again in the future.
Top guest favourite
Home in Yabucoa
4.97 out of 5 average rating, 106 reviews

Daddy’s Place Airbnb

KatRating, 5 stars5 days ago
We had a wonderful stay! The place was clean, and the pool was beautiful with an amazing view. My boys loved spending time in the pool. I especially enjoyed listening to the animal sounds at night— it was so peaceful. We’ll definitely be back next year!
Top guest favourite
Home in Punta Santiago
4.97 out of 5 average rating, 155 reviews

Lake and Beach Village, Humacao

JoannaRating, 5 stars6 days ago
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.
Guest favourite
Home in Carolina
4.87 out of 5 average rating, 113 reviews

The Leaves Apartments #2

AmyRating, 5 stars2 weeks ago
Zulmarie’s home was extremely comfortable! We felt extremely safe! She always responded right away! The house was beautiful! We had an amazing time!
Guest favourite
Home in Fajardo
4.89 out of 5 average rating, 123 reviews

Domirriqueña House

CarolineRating, 5 stars1 month ago
A relaxing experience, very clean, quiet place and the house contains everything you may need for your stay. I recommend it 100%. Hosts are very attentive and quick to respond. We were celebrating my son's birthday and Sandy decorated the room with balloons just as I requested. Exceeded my expectations. Thank you.
Top guest favourite
Home in Luquillo
4.97 out of 5 average rating, 121 reviews

Fabulous Ocean Views /Private Infinity Pool /4 BR

CourtneyRating, 5 stars2 weeks ago
I can’t say enough about this property! It’s a little slice of paradise. Even though it’s in a neighborhood it’s extremely private. The porches and pool area make you feel like you are at your own resort. The location is close to anything you might want to do in the east side of the island and Kevin provides a manual with excellent recommendations for restaurants, beaches, activities etc. We took advantage of so many but also used the well equipped kitchen and grills to eat in. The beach gear and towels were appreciated as were the washer/dryer. We had a couple of questions during our stay and Kevin was extremely responsive. Our family of 6 travelers, ages 13-74, had an awesome week!

Apartment rentals with a pool

Guest favourite
Apartment in Fajardo
4.83 out of 5 average rating, 294 reviews

Amazing ocean views & close to Bio Bay tours

WilRating, 5 stars3 months ago
Our stay at this studio apartment in Fajardo was nothing short of amazing! From the moment we arrived, we felt right at home. The apartment was extremely comfortable, well-equipped, and perfect for a relaxing getaway. The space was spotless, the bed was cozy, and all the amenities made our stay effortless and enjoyable. One of the absolute highlights was the breathtaking view. Waking up to the sight of the ocean and the stunning surroundings was an unforgettable experience. The location was also fantastic. We were just a short distance from several excellent restaurants, offering a variety of delicious local cuisine. Beyond the apartment itself, the atmosphere in Fajardo was incredible. The people were extremely friendly and welcoming. Overall, this was a perfect stay, and we would highly recommend this apartment to anyone looking for a relaxing, scenic, and convenient place to stay in Fajardo. We can’t wait to come back!
Guest favourite
Apartment in Fajardo
4.96 out of 5 average rating, 234 reviews

Ocean View Luxury Condo

WendyRating, 5 stars2 weeks ago
We’ve been staying at Airbnbs since the very beginning, and this was by far the nicest place we’ve ever stayed. The views were absolutely stunning, and the pool was so comfortable and inviting. We loved being within walking distance to dinner, our sailboat tour, and close to both the bioluminescent tour and the rainforest excursion. The kitchen was used daily and thoughtfully stocked with all the essentials—we truly appreciated every detail that was considered. Juan’s communication was exceptional—better than any host we’ve ever had. He called us ahead, made sure we got in okay & communicated clearly throughout the visit. The place was absolutely stunning. We couldn't imagine a better location or have had a better experience. Thank you again for your kindness and for allowing us to enjoy such a special place.
Top guest favourite
Apartment in Río Grande
4.99 out of 5 average rating, 152 reviews

Ocean View/Mountain Setting 3 - Owners Suite

JenniferRating, 5 stars2 weeks ago
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!
Superhost
Apartment in Fajardo
4.89 out of 5 average rating, 122 reviews

New! Breath Taking View at Las Casitas Village

RebeccaRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Fajardo
4.9 out of 5 average rating, 144 reviews

*Azul Marino* Golf & Ocean View Luxury Condo

CharlieRating, 5 stars1 week ago
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 !
Guest favourite
Apartment in Luquillo
4.94 out of 5 average rating, 215 reviews

Breathtaking Ocean View Apartment

EmmaRating, 5 stars1 month ago
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.
Superhost
Apartment in Luquillo
4.8 out of 5 average rating, 176 reviews

Beachfront Place at Condo Sandy Hills Luquillo, PR

CalistaRating, 5 stars2 weeks ago
Eric was very responsive and helpful. He was on top of sending me the check in instructions and check out instructions. The Airbnb itself is beautiful and perfect for a couple of days. The private beach access closes at 6pm which was inconvenient but that is my only complaint as we had to walk all the way around. It’s a good spot if you plan on visiting El Yunque and Fajardo. Safe area and people are really nice.
Top guest favourite
Apartment in Fajardo
4.95 out of 5 average rating, 104 reviews

Fajardo PR Modern Oceanfront Condo Million $ Views

KerenRating, 5 stars4 days ago
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

    ₹3,439 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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