Holiday rentals with outdoor seating in Roosevelt Roads

5 out of 5 average rating, 157 reviews

Home in Buena Vista

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.

ValueOutdoor spacesCheck-in

5 out of 5 average rating, 121 reviews

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-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.

Outdoor spacesValueTV

4.98 out of 5 average rating, 329 reviews

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

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!

Outdoor spacesValueComfort

4.94 out of 5 average rating, 108 reviews

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.

Condo in Machos

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.

LocationOutdoor spacesPool

4.98 out of 5 average rating, 146 reviews

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

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.

Outdoor spacesLocationBackyard

4.99 out of 5 average rating, 188 reviews

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

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.

LocationOutdoor spacesView

4.96 out of 5 average rating, 113 reviews

Tiny home in Luquillo

Private Rainforest Retreat ~10 min to Playa Azul~

Visiting El Yunque & Bio Bay? 🌺 Koko Kai Cabana is the perfect retreat - right between Luquillo and Fajardo - for exploring the Best of the East Coast 🇵🇷... You'll enjoy quiet, country life in the mountains of Juan Martin. But just 15 mins to Luquillo Beach, 20 to El Yunque or Bio Bay & shopping in Fajardo is only 7 mins down the mountain. We live on site, but the cabana is on the "3rd level" above the pool. It's private and tranquil... and everything is just for you two!

Outdoor spacesValueView

4.96 out of 5 average rating, 102 reviews

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

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.

LocationOutdoor spacesComfort

4.99 out of 5 average rating, 178 reviews

Home in Carolina

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

Outdoor spacesValueHospitality

5 out of 5 average rating, 440 reviews

The tiny house is presented against a backdrop of a vibrant rainbow, highlighting its blue exterior. An inviting deck with white seating is surrounded by tropical plants, while decorative string lights enhance the outdoor space, creating a relaxing and welcoming environment.

Tiny home in Ceiba

Self Sufficient Tiny House #1 River/Amazing Views

This 10’x16’ self-sufficient tiny house is a unique space on the mountain with everything you need to relax away from home. The views of the National rain forest and coastline are amazing. The Sonadora creek borders the 7.5 acre backyard and can be accessed through several paths in the property. The small kitchen is fully equipped for your convenience. It is 29 minutes to Ferry Terminal to Vieques/Culebra, 28 minutes to Seven Seas and 41 minutes to El Yunque.

ValueOutdoor spacesBathroom

Shipping container in Palmer

A cabin is surrounded by lush greenery, featuring a spacious wooden deck with seating. The structure's large windows offer clear views of the surroundings. A hammock is draped along the deck, and the landscape is accentuated by gentle hills and a blue sky with scattered clouds.

4.95 out of 5 average rating, 203 reviews

El Yunque Mountain View

This cabin has everything you need in a home away from home. It has a panoramic view to El Yunque and an amazing view to the Ocean, making it the perfect place for your romantic escape or to connect with nature. Location! This magical place is located 6min from El Yunque National Forest, 3 min from local restaurants, 9 min from los Kioskos de Luquillo and the best beaches. As an additional experience, you can book a massage during your stay!💕

LocationOutdoor spacesAmenities

4.92 out of 5 average rating, 108 reviews

Apartment in Ceiba

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!

ValueOutdoor spacesBathroom

Popular amenities for Roosevelt Roads outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.98 out of 5 average rating, 118 reviews

The exterior of the property features a vibrant combination of peach and cream walls, framed by neatly trimmed grass. A decorative metal fence offers entry, while rocking chairs are visible on the porch. The clear blue sky enhances the inviting atmosphere of the residence.

Home in Vieques

Casa Marin

LocationValueIndoor spaces

4.86 out of 5 average rating, 116 reviews

The exterior of a spacious two-story house is visible, featuring a wide terrace with white railing. Lush greenery surrounds the property, set against a backdrop of mountains under a cloudy sky. The driveway leads up to the entrance, showcasing various tropical plants along the way.

Home in Luquillo

Orquid Villa- Rainforest El Yunque amazing views

ValueLocationHospitality

4.92 out of 5 average rating, 308 reviews

Home in Humacao

Beautiful House, 24/7 Security, Gated Community

Outdoor spacesLocationBarbecue

Home in Bo. Las Cabezas, Las Croabas

An aerial view captures the vibrant coastal landscape featuring a cluster of homes surrounded by lush greenery. The serene expanse of the ocean gleams in the distance, with islands visible on the horizon under a clear sky.

4.92 out of 5 average rating, 165 reviews

Hidden Lighthouse Pool & Jacuzzi Ocean View in Fajardo

LocationValueAccess

4.91 out of 5 average rating, 163 reviews

A serene coastal view showcases a wooden pier leading into calm turquoise waters. In the distance, two green islands are visible against a backdrop of a bright blue sky adorned with scattered clouds. The sandy shore is gently lapped by the water's edge.

Home in Vieques

Relax & Explore, Walk to Bio Bay & Esperanza Beach

Outdoor spacesValueBathroom

4.95 out of 5 average rating, 193 reviews

The two-story property is surrounded by lush greenery, featuring a serene pond reflecting the building and sky. Lounge chairs are positioned on the grass, offering a relaxing spot to enjoy the natural surroundings.

Home in Río Grande

Hacienda Azucena, Río Grande, Yunque Rainforest

LocationOutdoor spacesKitchen

4.96 out of 5 average rating, 149 reviews

An infinity pool with illuminated edges provides a serene atmosphere during twilight. A swim-up bar is positioned at one side, while lounge chairs are visible nearby. A basketball hoop is set up next to the pool, and surrounding tropical foliage completes the tranquil outdoor space.

Home in Luquillo

Fabulous Ocean Views /Private Infinity Pool /4 BR

ValueLocationCheck-in

4.92 out of 5 average rating, 147 reviews

Home in Esperanza

Casa Amor Home Esperanza Salt Pool- close to Beach

Outdoor spacesValueLayout

Apartment rentals with outdoor seating

4.95 out of 5 average rating, 167 reviews

A spacious bedroom features a wooden bed frame with a neatly made bed, complemented by two bedside tables. Natural light enters through large windows. A comfortable seating area includes a light-colored sofa. Decorative elements include a modern light fixture and a wall art piece depicting a sailboat.

Apartment in Luquillo

Luquillo Mar HotTub Ocean View Studio

LocationOutdoor spacesAir conditioning

4.97 out of 5 average rating, 152 reviews

A glass filled with a beverage is positioned on a wooden railing. In the background, lush greenery and vibrant red plants are visible against a bright blue sky, with fluffy white clouds adding texture to the scene. The horizon showcases the expansive landscape.

Apartment in Río Grande

El Yunque @ La Vue

Outdoor spacesValueBarbecue

4.92 out of 5 average rating, 102 reviews

Apartment in Fajardo

Dream Bay PR: Romantic Terrace, El Yunque & Ferry

LocationOutdoor spacesKitchen

4.93 out of 5 average rating, 134 reviews

Apartment in Fajardo

Wake Up to Ocean Views | Pool + Marina Paradise

LocationTVPool

4.92 out of 5 average rating, 206 reviews

A living room space is displayed with large windows offering ocean views. Comfortable seating arrangements include a gray sofa and an armchair, with a coffee table at the center. Natural light illuminates the room, enhancing the serene atmosphere.

Apartment in Fajardo

Stunning Ocean Front Resort Villa at las Casitas.

LocationValueAccuracy

4.94 out of 5 average rating, 110 reviews

A modern kitchen and dining area are highlighted by vibrant red cabinetry and stainless steel appliances. A glass table is surrounded by four turquoise chairs. Artwork featuring colorful parrots adorns the wall, complementing the bright and airy atmosphere of the space.

Apartment in PR

Beach Front Suite

ValueLocationAir conditioning

4.95 out of 5 average rating, 105 reviews

A spacious rooftop terrace showcases a vibrant sunset over lush greenery. Comfortable lounge chairs are positioned for relaxation, with wooden dining furniture providing an area for meals. The open space is framed by two angled roofs, allowing for expansive views of the surroundings.

Apartment in Vieques

Big Sky -2 Bedroom Walk to Town!

ValueLocationCheckout

Apartment in Alturas de Monte Brisas, Fajardo

An outdoor patio area is presented, featuring a thatched umbrella over a dining table and various seating options. Colorful cushions adorn a wooden bench. String lights and a Puerto Rican flag add character to the space, surrounded by greenery and a white picket fence.

4.92 out of 5 average rating, 229 reviews

Julia Apartments 2

LocationValueLong stay

Condo rentals with outdoor seating

4.9 out of 5 average rating, 225 reviews

Condo in Machos

Oceanview Bay View Penthouse Beach/Marina/Ferry

LocationOutdoor spacesCondition

Superhost

An aerial view captures the expansive marina lined with yachts, set against lush green hills and a clear blue sky. Calm waters reflect the vibrant hues, while a small sailboat is visible, subtly enhancing the coastal scene. The shore features a mix of residences and greenery.

4.87 out of 5 average rating, 208 reviews

Aqua Salada Window 27, with Ocean/Marina View

LocationValueCheckout

4.94 out of 5 average rating, 174 reviews

A modern living area is shown with a green sofa adorned with colorful cushions. A round wooden coffee table occupies the center, featuring decorative items. The kitchen is equipped with stainless steel appliances and white cabinetry, enhancing the inviting layout. Natural light pours through large windows.

Condo in Playa Fortuna

Restful Beachfront Private Oasis

Outdoor spacesLocationView

4.99 out of 5 average rating, 177 reviews

A tranquil pool is framed by wooden decking, offering clear views of the ocean and surrounding greenery. Sun loungers are positioned along the edge, inviting relaxation. The horizon showcases a blend of blue skies and distant clouds.

Condo in Río Grande

Ocean View/Mountain Setting 3 - Owners Suite

LocationOutdoor spacesWi-Fi

4.95 out of 5 average rating, 118 reviews

Villa @ Marina; Near Beach/Easy Access to Islands

ValueLocationPool

4.98 out of 5 average rating, 102 reviews

Condo in Luquillo

Ocean View-2Level Penthouse w Balcony • Luquillo

LocationValueQuiet

A panoramic view of the ocean highlights varying shades of blue and turquoise water. The coastline is visible in the background, framed by lush green hills under a partly cloudy sky. A boat can be seen cruising through the waters, adding a dynamic element to the serene landscape.

4.96 out of 5 average rating, 189 reviews

Beachfront Luxury Apartment w/ Amazing Views

LocationValuePool

A panoramic view showcases the vibrant turquoise waters of the ocean, bordered by lush green hills. The marina is visible in the foreground with boats docked, while gentle waves and a clear sky complete the tranquil coastal scene.