
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.
Holiday rentals for every style
Get the amount of space that is right for you
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!!

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
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.

Daddy’s Place Airbnb
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!

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!

Domirriqueña House
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.

Fabulous Ocean Views /Private Infinity Pool /4 BR
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

Amazing ocean views & close to Bio Bay tours
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!

Ocean View Luxury Condo
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.

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 !

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.

Beachfront Place at Condo Sandy Hills Luquillo, PR
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.

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
₹3,439 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
Destinations to explore
- Carolina Holiday rentals
- Culebra Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Tortola Holiday rentals
- Luquillo Holiday rentals
- Fajardo Holiday rentals
- Ponce Holiday rentals
- Santo Domingo Holiday rentals
- San Juan Holiday rentals
- Punta Cana Holiday rentals
- Las Terrenas Holiday rentals
- Rentals with beach access Roosevelt Roads
- Rentals with outdoor seating Roosevelt Roads
- Rentals with a washing machine and dryer Roosevelt Roads
- House rentals Roosevelt Roads
- Apartment rentals Roosevelt Roads
- Family-friendly rentals Roosevelt Roads
- Fitness-friendly rentals Roosevelt Roads
- Family-friendly rentals Roosevelt Roads
- Flat rentals Roosevelt Roads
- Rentals with a patio Roosevelt Roads
- Pet-friendly rentals Roosevelt Roads
- Rentals with pools Ceiba Region
- Rentals with pools Puerto Rico
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Rio Mar Village
- Distrito T-Mobile
- Praia de Luquillo
- Playa del Dorado
- Liquillo Beach
- Playa Sun Bay
- Playa el Convento
- Beach Planes
- Toro Verde Adventure Park
- Carabali Rainforest Park
- Playa Puerto Real
- Coco Beach Golf Club
- Playa Maunabo
- Hull Bay Beach
- Mandahl Bay Beach
- Playa Las Palmas
- The Saint Regis Bahia Golf Course
- Playa de Cerro Gordo
- Punta Bandera Luquillo PR