Vacation rentals with a pool in Roosevelt Roads

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Top-rated rentals with a pool in Roosevelt Roads

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Guest favorite

Apartment in CEIBA

4.89 out of 5 average rating, 132 reviews

Hacienda Torres Paradise of Nature - Villa Limon

2 bedroom, 1 bathroom apartment in the middle of a 40 acre private property with peaceful ambiance. We have very friendly farm dogs that are loose and will interact with guests. Seasonal fruits are available for your delight when available mangoes avocados, breadfruit, guava, coconuts, starfruit. You will be serenated by birds during the day and coquis at night! 5 min access to highway #53. Near beaches, marinas, restaurants, ferry to Culebra and Vieques islands and Roosevelt Roads Airport.

Jan 22 – 29

G$29,457 GYD per night

Guest favorite

Condo in Machos, Puerto Rico

4.9 out of 5 average rating, 126 reviews

OCEAN VIEW-Vista Bahía Penthouse near Marina-Ferry

Enjoy your island escape at "Vista Bahía Penthouse" in Costa Esmeralda. There is something special about Ceiba – sleeping away from the hustle and bustle of everyday life and only minutes away from multiple activities and places you will enjoy. 3 to 5 minutes to marina, beaches, restaurants, shopping, and more. Wake up to sunrises right outside your window. The condo features 3 bedrooms air-conditioned, kitchen with all the convenience. Relax on the private rooftop with ocean panoramic views!

Jan 30 – Feb 6

G$29,751 GYD per night

Guest favorite

Apartment in Vieques

4.98 out of 5 average rating, 101 reviews

1BR/W - Spectacular Ocean View/Pool/Walk to Beach

"Villa del Sol" is a delightful, modern villa with our apartment upstairs and two spacious 1BR apartments below. Perched up high with panoramic views of the ocean, it is just a 5-minute walk from two secluded beaches. Fully gated, it has a paved drive and parking, and an in-ground pool. This charming 1BR apartment has high quality furniture and furnishings, a fully equipped kitchen, a large bedroom, flatscreen TV, WIFI & AC. * * * CLICK ON "Show More" BELOW TO CONTINUE THE DESCRIPTION * * *

Oct 8 – 15

G$33,453 GYD per night

Guest favorite

Apartment in Cabezas

4.96 out of 5 average rating, 101 reviews

Luxury Ocean Front Studio

Luxurious beachfront apartment to spend a beautiful day. It is located next to the Hotel El Conquistador with an incredible view. With a view to the sea, you can see Palomino Island, Icaco Cay, Island Culebra and Vieques. This apartment is unique, romantic and elegant to have a good time. It has different attractions nearby such as the Yunque, Seven Seas Beach,Snorkel and beach tours, Ferry to Culebra and Vieques. Different areas for night activities such as the Bio Bay in the Croabas.

Oct 13 – 20

G$30,346 GYD per night

Guest favorite

Apartment in Ceiba

4.9 out of 5 average rating, 108 reviews

Mountainside Ocean View Pool/Family Fun Ferry

Experience Puerto Rico's rainforest at our mountaintop apartment. Coqui's and owls create a natural background at night. 1 full apartment including garage parking. Full kitchen, full bedroom, living room converts to a queen bed. 18' pool with ocean view 12' gazebo. 3 acres of trails to hike, trampoline, and zip line for children. kayak and beach equipment. transportation to ferry available. Our boat is also available seek a water adventure. very kid friendly - must be ok with dogs.

Dec 6 – 13

G$14,944 GYD per night

Guest favorite

Condo in Ceiba, Fajardo

4.97 out of 5 average rating, 193 reviews

Rooftop Views "Kasa Playera" Ferry|Marina|Airport

This amazing 2-story Penthouse offers breathtaking views of Culebra and Vieques Islands. With 3 bedrooms, 2 bathrooms, a rooftop terrace, and the exclusive distinction of being the only property in the community with a reliable power backup system, it provides all the comforts and conveniences you need. Located near Marina Puerto del Rey, Ceiba Airport, and the Ceiba Ferry Terminal; it definitely offers easy access to a variety of exciting activities. Create unforgettable family memories!

Jul 7 – 14

G$51,639 GYD per night

Guest favorite

Guest suite in Luquillo

5.0 out of 5 average rating, 107 reviews

Casa Encanto - Experience Yunque Rain Forest

This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Pailas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup

Apr 4 – 11

G$70,576 GYD per night

Guest favorite

Apartment in Ceiba

4.94 out of 5 average rating, 217 reviews

El Capitan - Heavenly Paradise Apartments

El Capitán is a semi-detached apartment with a separate entrance from the property's main house. Our retro tropical themed apartment is equipped with A/C, WI-FI, access to the pool area, kitchen, and many other wonderful amenities. With a convenient location, El Capitan is just about 18 minutes away by car from the Ceiba Ferry Terminal, which is were you can take ferries to the islands of Culebra and Vieques and about 45 minutes from El Yunque Rainforest. You'll feel right at home.

Jan 4 – 11

G$18,475 GYD per night

Guest favorite

Condo in Fajardo

4.9 out of 5 average rating, 165 reviews

Stylish Oceanfront Apartment!+Pool +AC 28th floor

Unwind at this beautiful Fajardo beachside condo. Wake up to a beautiful view of a Caribbean sunrise & fall sleep with the sounds of waves crashing against the shore. Enjoy Fajardo’s amazing coastline, nearby islands and cays & the rain forest. Shops and amazing sea food are few minutes drive away, but the area is peaceful & secluded. The property offers pool, gated parking, & free Wifi. The apt consists of 1 BD with a queen bed, 1 BA, a sofa bed. and an amazing ocean view.

Apr 24 – May 1

G$20,715 GYD per night

Guest favorite

Condo in Fajardo

4.95 out of 5 average rating, 275 reviews

Our slice of paradise

Spacious studio apartment, located on the 22nd floor with stunning views of the East Coast Icacos and Palomino Islands. Unit has cooktop, microwave, and full size refrigerator. Kitchen is also equipped with utensils, crockery and cutlery. The complex has a laundry area on ground floor with washer and dryer for a small fee. It also has a swimming pool, tennis court, basket ball court and 24/7 security. It’s the perfect place to enjoy the breeze and relax.

Sep 14 – 21

G$23,518 GYD per night

Guest favorite

Condo in Fajardo

4.96 out of 5 average rating, 109 reviews

The ReFresh | Warm minimalist seaviewing retreat

Welcome to @TheReFresh! 🔆 Your serene minimalist modern marina-viewing & seaviewing retreat! At a full 775 sqft at a 19th floor, ease into your most relaxed state enjoying the Caribbean in the comfort of your sea breezed space. 🍂🌅 🌟 PERK: You'll be 10 minutes away from the beach, the marinas and many family-friendly aventures. ⛵️🏖🌺 ❗️Note: The Seven Seas Beach's main road is under construction, but the beach is open.

Nov 2 – 9

G$23,546 GYD per night

Guest favorite

Apartment in Ceiba

4.96 out of 5 average rating, 127 reviews

Escape to Costa Brava

Apartamento tropical con vista relajante al mar desde su balcón y de cada una de sus habitaciones, es tu mejor opción. Disfrute de la tranquilidad y la comodidad de nuestro apartamento. Puede alojar cómodamente 8 personas, lo hemos preparado para que te sientas como en casa. Nuestro objetivo es que tengas unas vacaciones inolvidables y sin preocupaciones, escápate de fin de semana o días de semana.

Feb 16 – 23

G$20,835 GYD per night