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Holiday rentals in Roosevelt Roads

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Roosevelt Roads

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The property is nestled on a hillside, surrounded by lush greenery and tropical plants. The building features a rooftop terrace with sweeping views of the landscape and clouds above, showcasing the natural beauty of the coastal region.
Cottage in Ceiba
4.99 out of 5 average rating, 137 reviews

Mi Estela

Este Airbnb es acogedor y cálido, con muebles de madera y textiles suaves que invitan a relajarse. La decoración es inspiradora, con detalles únicos, obras de arte locales y plantas que crean un ambiente creativo. El espacio es relajante, con una terraza rodeada de una vista espectacular de la costa Este de PR ideal para familias, con una cocina funcional y áreas de juego que hacen que todos se sientan como en casa. Además, el vecindario es seguro, garantizando una estancia tranquila y cómoda.

Top guest favourite
Home in Buena Vista
5 out of 5 average rating, 157 reviews

Private Nature Retreat • Hot Tub • Ocean Views

Private countryside retreat in Humacao with distant ocean views, mountain scenery, and peaceful coquí sounds at night. Relax in the hot tub surrounded by nature while staying close to beaches, hiking, local food spots, and authentic Puerto Rico culture. Quiet and private, away from crowded tourist areas yet centrally located for exploring eastern Puerto Rico — ~45 min to El Yunque, ~25 min to Ceiba Ferry, and 10–45 min to beaches depending on the area. Full A/C, fast WiFi, BBQ & self check-in.

Top guest favourite
The inviting bedroom features a spacious bed adorned with patterned pillows and a quilt. Rolled towels are neatly placed next to a bright sunflower and a welcome book, enhancing the area with warmth and charm.
Place to stay in Ceiba
5 out of 5 average rating, 121 reviews

5-Star Private Suite Getaway with Unmatched Views

A perfect getaway in our stunning mountain retreat, nestled in the serenity & heart of El Yunque National Forest. As a 5-star Superhost, we pride ourselves on providing an unforgettable experience for our guests. Breathtaking views for spectacular sunsets, overlooking the sparkling ocean. Our unique location offers a peaceful escape from the hustle of city. We pay attention to every detail to ensure your comfort & satisfaction. Reconnect with nature, unwind in luxury & create lasting memories.

Guest favourite
A wooden terrace is shown with a stool positioned near the railing. The sun rises above a distant landscape, casting warm light over lush green hills and the ocean. An infinity pool is visible nearby, blending beautifully with the scenic surroundings.
Tiny home in Fajardo
4.98 out of 5 average rating, 328 reviews

Magical! Ocean view Cabana w/ Pool Spa on mountain

This memorable place is anything but ordinary. You will get to enjoy this amazing and super private space surrounded by nature and unbelievable views of the ocean and the city. Fully equipped with everything you will need during your stay to include kitchen, full bath with rain shower, A/C, living space with 55" TV, dinning and sleeping areas, terrace with killer views, and of course the pool spa with infinity view! And many more. All of this while enjoying of a complementary bottle of Wine!

Top guest favourite
A modern living area features a black leather sofa, a circular coffee table, and a woven area rug. Natural light floods the space through large glass doors, leading to a balcony. A TV and workspace are also visible, complementing the contemporary design.
Apartment in Machos
4.94 out of 5 average rating, 108 reviews

Oceanview Penthouse / Private Rooftop • Near Ferry

Wake up to ocean views and unwind on your private rooftop in Puerto Rico’s beautiful east side — just 8 minutes from the Ceiba ferry to Vieques & Culebra. This spacious 3-bedroom, 2-bath penthouse is located in a gated community with on-site security, 2 free parking spaces, and a private rooftop perfect for sunrise coffee, stargazing, and relaxing after a beach day. Minutes from beaches, Luquillo kiosks, El Yunque, Las Croabas, and some of the best experiences on Puerto Rico’s east coast.

Guest favourite
Flat in Ceiba
4.81 out of 5 average rating, 217 reviews

Salmos 23 apartment/Cerca del terminal de lanchas.

Hospédate en el casco urbano de Ceiba, cerca del terminal de lanchas a Vieques y Culebra. Acceso rápido a: 🌊 Fajardo: playas, catamaranes y bahía bioluminiscente. 🏝️ Luquillo: Balneario La Monserrate y kioscos. 🌳 Río Grande y El Yunque: senderos y cascadas. 🌅 Naguabo: malecón y restaurantes frente al mar. Céntrico y cómodo: restaurantes, supermercados, panaderías y farmacias cerca. Perfecto para quienes buscan tranquilidad, ubicación estratégica y explorar el este de Puerto Rico.

Superhost
A serene pool area is framed by tropical palm trees, with a gazebo featuring string lights in the foreground. The pool reflects the evening sky, while lush greenery surrounds the space, providing a sense of tranquility and natural beauty.
Flat in Ceiba
4.83 out of 5 average rating, 188 reviews

Mountainside Ocean View & Pool Treasure Hunt 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.

Top guest favourite
A contemporary house is positioned atop a hill, surrounded by lush greenery and palm trees. A winding pathway leads to the entrance, while panoramic ocean views extend in the background, highlighting the beauty of the surrounding landscape.
Home in Ceiba
4.98 out of 5 average rating, 146 reviews

La Casita: Private Heated Pool W/ Ocean Views

Nestled atop a lush hill at the beachfront town of Ceiba, this 2-bedroom house is a haven of luxury & tranquility, offering a spectacular panoramic view of the ocean, the rainforest, mountains & neighboring islands. As you approach the property, a winding driveway bordered by vibrant, blooming flowers leads you to the entrance, setting the tone for the enchanting retreat that awaits. Just a 1-hour drive from SJU's International Airport & half hour ride from El Yunque National Rainforest.

Top guest favourite
A tranquil outdoor pool is seen, featuring a sunbathing area with two sleek lounge chairs. The pool's clear water reflects the bright blue sky with fluffy clouds, while tropical plants enhance the scenic mountainous backdrop.
Tiny home in Naguabo
4.99 out of 5 average rating, 187 reviews

Casa Suiza-Private Couple Escape with Heated Pool

Casa Suiza es un retiro de escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos ubicados en la montaña, es muy privado, alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña. Una vez comienzas a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables.

Guest favourite
Flat in Fajardo
4.93 out of 5 average rating, 133 reviews

Wake Up to Ocean Views | Pool + Marina Paradise

A tranquil getaway in this stunning apartment with breathtaking ocean views. Step inside to discover modern updates & stylish design. The exclusive 2 suites feature beautiful windows, offering unobstructed view Unwind by the giant pool or enjoy the sunrise from the expansive balcony—perfect spots for relaxation. The fully equipped kitchen with exotic white granite countertops is ideal for whipping up meals. This is the perfect retreat for those seeking luxury & serenity!

Superhost
Villa in Roosevelt Roads
4.85 out of 5 average rating, 34 reviews

Mami Ana Beach House: The oceanfront rest hideaway

Wake up to a postcard-worthy view and enjoy unforgettable sunsets by the sea. This cozy home is a charming fisherman’s villa with the perfect spot to disconnect and simply enjoy the ocean. Although the beach isn’t always ideal for swimming due to seaweed, it’s great for fishing or kayaking (extra cost) to discover the coast from a different angle. You can also spend a perfect day having a BBQ. Its location is ideal for exploring beautiful nearby beaches!

Guest favourite
Flat in Ceiba
4.92 out of 5 average rating, 108 reviews

Casa Ceiba 2

Enjoy comfort and convenience at Casa Ceiba, just 15 minutes from the Ferry Terminal and 10 minutes from Ceiba Airport. Located in the heart of Ceiba near rivers, beaches, Marina, supermarket, bakery, restaurants, bars, and a gas station with mini market. Only 2 minutes from Highway PR-53. *Disclaimer:* Due to road construction nearby, traffic is being diverted to our street and may cause some noise. We appreciate your understanding!

Popular amenities for Roosevelt Roads holiday rentals

When is the best time to visit Roosevelt Roads?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Roosevelt Roads?

    Roosevelt Roads has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Roosevelt Roads?

    Experience the best of Roosevelt Roads with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Roosevelt Roads?

    Four-legged friends are welcome in Roosevelt Roads. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Roosevelt Roads?

    Yes! Work meets play with ease at over 20 house rentals in Roosevelt Roads featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Roosevelt Roads house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Roosevelt Roads, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Roosevelt Roads have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Roosevelt Roads. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Roosevelt Roads have a kitchen?

    Absolutely! We offer over 80 apartment rentals with a kitchen in Roosevelt Roads. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Roosevelt Roads have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Roosevelt Roads. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Roosevelt Roads have free parking?

    Absolutely! We offer over 20 condo rentals with free parking in Roosevelt Roads. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Roosevelt Roads?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 50 homes with wifi, over 50 homes with a kitchen, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Roosevelt Roads

  • Total holiday rentals

    Explore 190 holiday rentals in Roosevelt Roads

  • Nightly prices starting at

    Roosevelt Roads holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 12,650 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    190 of Roosevelt Roads holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Roosevelt Roads rentals

  • 4.8 Average rating

    Roosevelt Roads stays are highly rated by guests – averaging 4.8 out of 5!

  1. Airbnb
  2. Puerto Rico
  3. Ceiba
  4. Roosevelt Roads