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House holiday rentals in Roosevelt Roads

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Top-rated house rentals in Roosevelt Roads

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

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Guest favourite
A comfortable lounge area is furnished with two reclining chairs facing a large flat-screen television, mounted on a dark wall. Shelving units feature subtle decor items, while soft lighting enhances the space's ambiance. Potted plants add a touch of greenery to the setting.
Home in Ceiba
4.94 out of 5 average rating, 115 reviews

Casa Escape Close to the ferry (Vieques and Culebra)

At CASA ESCAPE you'll be close to everything. You will find several businesses in the center of town, including restaurants, bakeries, pharmacies, a bank and others. You will be 8 minutes from the Vieques and Culebra Ferry Terminal, 3 minutes from Playa Medio Mundo, 3 minutes from Marina Puerto del Rey, 15 minutes from Villa Marina Villa, 20 minutes from Las Croabas and Seven Sea Beach, where you will find a variety of restaurants and recreational activities, 15 minutes from the kiosks and Luquillo Beach and 25 minutes from the Yunque National Forest.

Guest favourite
Home in Humacao
4.92 out of 5 average rating, 306 reviews

Beautiful House, 24/7 Security, Gated Community

Sanitized! Beautiful and comfortable residence with Private Pool, Jacuzzi and Grill. 12min from Palmas del Mar that has beach, bars, night life and sea food restaurant. Minutes from Palma Real Mall, Walmart, restaurants, fast food & much more. 45 min to the airport, 50 min to Old San Juan. 20 min from El Malecon de Naguabo which has many Seafood Restaurants, and beach. 30min to the boat terminal to go to Vieques and Culebra, 40 min from Luquillo Kiosk, 35 min from the Croabas You must rent a car

Guest favourite
Home in Luquillo
4.92 out of 5 average rating, 211 reviews

Enchanted Pool Beach House

Take it easy at this tropical and peaceful getaway with a private pool where is only for the guest staying at the house. The house is 5 minutes away from many beaches like La Pared Beach, Playa Azul, Costa Azul Beach, Balneario La Monserrate Luquillo and Northeast Ecological Corridor. 10 minutes away from Bioluminescent Bay and Seaven Seas Beach in Fajardo. Also 15 minutes away from El Yunque National Forest in Rio Grande and 5 minutes from Caribbean Cinemas Theater, Shopping mall and Pharmacy.

Top guest favourite
A covered terrace features a hammock and seating area with white furniture. Lush greenery surrounds the space, while ocean views are visible in the distance. Natural light illuminates the wooden structure, enhancing the connection with the outdoors.
Home in Buena Vista
5 out of 5 average rating, 154 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.

Guest favourite
A spacious outdoor area features two lounge chairs with a small table, positioned on lush green grass. A private Jacuzzi is visible nearby, with palm trees framing the scene. A tent-style shade and a hammock complete the inviting outdoor setting.
Home in Luquillo
4.93 out of 5 average rating, 148 reviews

Beautiful Rooftop Getaway | Jacuzzi by Rainforest

We invite you to stay at our home with breathtaking views of Puerto Rico's coastline! - 4 bedrooms with AC, 2.5 bathrooms, BBQ, 3 SmartTVs, fast Wi-Fi, and more - Private Jacuzzi with a stunning view - Generator & water tank available - Access to neighborhood pool, 24/7 security, and just 5 minutes from Luquillo Beach - Close to the rainforest, catamarans, kayaking, snorkeling tours, and more - Private chef and boat tours available - No loud music, parties, or events - We are Airbnb Superhost!

Top guest favourite
The exterior of Casa Tesoro features a whitewashed facade with a welcoming balcony and ceiling fans. A prominent sign with the name 'Casa Tesoro' is displayed at the entrance, surrounded by a gated fence, offering a private and secure ambiance.
Home in Vieques
4.99 out of 5 average rating, 145 reviews

Casa Tesoro-pool home. Walk to beaches/restaurants

Newly renovated home with constant ocean breezes and breathtaking views of the Caribbean Sea and Esperanza Keys. This home offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. We are located in the heart of Esperanza, no car is needed as we are less than a 5 minute walk to the Malecon, Restaurants and 2 minutes to the neighborhood Grocery store. Coco, Esperanza and Sun Bay beaches are a short walk away or enjoy your private pool, one of a few in Esperanza.

Guest favourite
A spacious balcony is shown with a hammock gently swaying. Tropical plants are presented in a pot beside the railing. A clear blue sky and expansive ocean view create a serene backdrop, enhancing the feeling of relaxation in this outdoor space.
Home in Fajardo
4.93 out of 5 average rating, 172 reviews

Casa Margot #2

Rest in a place with a spectacular ocean view . Close to the best places in Fajardo, a few minutes from Marinas, Bakery, Laundry, Restaurants. A few minutes by car from Seven Seas Beach, Bioluminescent Lagoon, Restaurants. The accommodation is located on the second level of the property. Access is from the left side of the property and you will find a small staircase at the back. ➡️ It is preferable to move by car. ➡️ Or you can call an Uber or Taxi also arrive at the Accommodation.

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, 145 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.

Guest favourite
Home in Fajardo
4.84 out of 5 average rating, 449 reviews

Entire property in Fajardo 5 minutes from ferry

Your East Tropical Escape in Fajardo, Bella!!, Two story house on a corner, private, nice patio with pool, 5 minutes to Vieques and Culebra's ferry. Close to the Bio Bay in Las Croabas, 3 minutes from grocery stores, pharmacies and restaurants. Gated community with security, common areas with a nice pool, tennis, volley ball and basket ball courts, close to beautiful beaches, kayaking, 20 minutes from the Rain Forest (El Yunque), a must see! 1 minute from Marina Puerto Del Rey.

Top guest favourite
A modern structure is set amidst lush greenery, featuring a light-colored exterior with large windows. A pathway leads to the entrance, bordered by neat outdoor lighting fixtures. Palm trees provide a tropical ambiance, contributing to a serene and inviting atmosphere.
Home in Naguabo
4.96 out of 5 average rating, 100 reviews

Skirt of EL Yunque (45 mins from Airport)

This Gem provides enchanting blends of breathtaking views and a serene atmosphere. Buckle up, adventurers, because the drive to this property is anything but ordinary! Brace yourselves for a thrilling and pulse-pounding journey that will push your limits. Steep hills that seem to touch the sky, winding roads that twist and turn, along with portions of it so narrow that it feels like navigating through a secret passageway into the Rainforest. NOT HANDICAP ENABLED.

Top guest favourite
Home in Carolina
4.99 out of 5 average rating, 177 reviews

Hilltop Cabin w/ Pool & Views – 18 Mins to Airport

✈️ 18 min to airport & 🏖️ top beaches 🏊 Private pool, loungers & hammocks 🌿 Peaceful countryside, just 5 min to city 🌴 45 min to El Yunque & Luquillo Beach 🏡 Hilltop cabin with ocean & mountain views 🛏 Queen bed + full pull-out bed (sleeps 4) 🍽 Indoor + outdoor dining for 4 with views 🚿 Outdoor shower (perfect after the beach) 🌅 Stunning sunrise views from elevated setting ⚡ Fast WiFi, A/C, Smart TV & gated parking 🪑 Beach chairs, cooler & beach towels

Top guest favourite
A comfortably arranged sleeping area features a spacious bed with a light-colored coverlet. Soft, ambient lighting frames the headboard, while two bedside lamps provide additional illumination. A decorative tray rests on the bed, enhancing the welcoming look of the room.
Home in Ceiba
4.99 out of 5 average rating, 452 reviews

Brisas de Ceiba, a Refuge of Love near the Ferry

The ferry is 10-15 minutes away. Also 6 minutes away we have a small airport called (José Aponte) where you are given services to travel by plane to the Virgin Islands including Vieques and Culebra. 7 minutes away you can also visit La Playa Machos and Playa Medio Mundo which are good for hiking. 10 minutes away we have Puerto Rey where they offer excursions to go to Isla Icaco

Popular amenities for house rentals in Roosevelt Roads

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Avg. price$152 SGD$166 SGD$169 SGD$170 SGD$169 SGD$166 SGD$166 SGD$174 SGD$162 SGD$146 SGD$158 SGD$153 SGD
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Quick stats about house rentals in Roosevelt Roads

  • Total holiday rentals

    Explore 50 holiday rentals in Roosevelt Roads

  • Nightly prices starting at

    Roosevelt Roads holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,720 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 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!

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