Roosevelt Roads Vacation Rentals from ￥20,299: Search Short-Term Rentals

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In two months

In three months

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Our top choices for Roosevelt Roads vacation rentals

A beach with a palm tree, sandy shore, and calm water.

1. Mami Ana Beach House.10min ferry Vieques/Culebra. Beautifull, excelent location

Ceiba

Duane

￥35,574 total

includes taxes & fees

Sep 27 - Sep 28

A covered outdoor area with a view of hills, a wooden bench, and a table.

2. The Ceiba Villa by Otium

Río Abajo

Chidera

￥25,734 total

includes taxes & fees

Sep 28 - Sep 29

A bedroom with a bed, two armchairs, a bedside table, a decorative wall piece, and a small potted plant.

3. Playa Colorá

Cabezas

carlos

￥20,299 total

includes taxes & fees

Sep 29 - Sep 30

A modern living room with two wicker chairs, a dark coffee table, and a potted plant.

4. Playa icacos

Cabezas

Gladys

￥20,383 total

includes taxes & fees

Sep 26 - Sep 27

A rustic outdoor dining area with wooden structures and thatched roofs, surrounded by trees.

5. Wonderful 2-bedroom cottage with AC in charming Ceiba. Minutes from the Ferry.

Ceiba

brian g.

￥26,080 total

includes taxes & fees

Sep 27 - Sep 28

A modern living room with a dining area, a grey sofa, a coffee table, and a potted plant.

6. Costa Brava Condo by Otium

Ceiba

Esmeralda

￥54,810 total

includes taxes & fees

Oct 26 - Oct 27

A beach with a palm tree leaning towards the ocean, sandy shore, and a cloudy sky.

7. Beautiful apartment in Fajardo

Fajardo

Jacob M.

￥23,487 total

includes taxes & fees

Oct 1 - Oct 2

A pool with a view of lush greenery and mountains.

8. Villa Mango

Fajardo

Milagros

￥26,391 total

includes taxes & fees

Oct 1 - Oct 2

A person standing on a wooden deck overlooking a waterfall and lush greenery.

9. El Yunque Rainforest

Naguabo

Leslie

￥39,367 total

includes taxes & fees

Oct 1 - Oct 2

A modern two-story house with three numbered doors, a paved driveway, and a well-maintained lawn.

10. Charming and Private Stay in Fajardo - Near Ferry - Beaches - EL Yunque - Biobay

Fajardo

Elaine De

￥21,995 total

includes taxes & fees

Oct 5 - Oct 6

A bedroom with a bed, a hanging coat rack, and three wall-mounted decorative panels.

11. Colmado by Otium

Zarzal

￥20,401 total

includes taxes & fees

Sep 28 - Sep 29

A modern living room with a balcony, a ceiling fan, and a view of the cityscape.

12. Family friendly place for those looking for adventure, beach, and great food!

Ceiba

Melissa

￥46,762 total

includes taxes & fees

Sep 27 - Sep 28

13. Casa Parcha

Naguabo

Marian

￥31,164 total

includes taxes & fees

Sep 27 - Sep 28

A dining area with a table, chairs, and a mirror.

14. La Casita del Este

Fajardo

Kristina M.

￥30,927 total

includes taxes & fees

Oct 1 - Oct 2

A building with a blue roof and white walls, surrounded by potted plants and a yellow curb.

15. Playa palomino

Cabezas

Diamond

￥26,567 total

includes taxes & fees

Sep 29 - Sep 30

An outdoor kitchen with a gas stove, sink, and stone counter.

16. Garden Suite near the Beach and restaurants!

Ucares

Gladys

￥32,271 total

includes taxes & fees

Oct 1 - Oct 2

An aerial view of a coastal area with a beach, dense forest, and clear turquoise waters.

17. Marina villa 3 bed 2-bathroom full kitchen equipped: electric generator

Fajardo

margie

￥44,573 total

includes taxes & fees

Sep 28 - Sep 29

A balcony with a hammock, a potted plant, and a wooden table.

18. Luxury Penthouse w/ Ocean & Marina Views • Pool

Fajardo

Suzanne

￥70,979 total

includes taxes & fees

Oct 1 - Oct 2

A modern kitchen with a central island, pendant lighting, and a dining area with chairs and a table set for two.

19. Sea Breeze Escape | Sleeps 7 + Pool in Ceiba

Ceiba

Jeremiah H.

￥39,553 total

includes taxes & fees

Oct 7 - Oct 8

A multi-story building with balconies, a flat roof, and a grassy lawn in front.

20. Spacious 3 bedroom apartment with sea view short drive to Ceiba ferry station.

Ceiba

Anonymous traveler

￥43,831 total

includes taxes & fees

Sep 26 - Sep 27

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Top Roosevelt Roads Hotel Reviews

El Conquistador Resort

10/10 Excellent

"Excelente"

Selva Boutique Hotel - Luquillo Oceanfront Retreat - Adults only

10/10 Excellent

"My stay at Selva was absolutely beautiful. From the moment I arrived, the place felt like home. The breathtaking ocean views from my room were amazing and made the experience even more special. The owner was incredibly down-to-earth, welcoming, and genuinely cool. There’s also a bar on the property with beautiful ocean views, which was the perfect spot to relax, take in the ocean vibes, and enjoy their signature sangria—it was delicious! I also loved how pet-friendly the property is. The cat and dog were such a sweet addition and made the place feel even more welcoming. Overall, my experience was exactly what I had hoped for and more. I’m so grateful I gave this place a chance. I truly enjoyed my stay and would definitely reserve here again. Highly recommended!"

CALIZO VIP GUEST HOUSE

10/10 Excellent

"We love, love, LOVED our room and the whole place! You enter into a super cute court yard, the room was spacious, really clean and super cute. Staff was super helpful and accommodating. We had a great stay. The pool area was nice and also super clean. Would highly recommend. There is a little Cafe next door that was great too!"

Mata e' Platano Guesthouse

10/10 Excellent

"Without a doubt, our stay at Mata ‘e Platano was amazing! The photos don’t do this property justice—it is even more breathtaking in person. The landscaping and outdoor spaces are beautiful, tranquil, and exceptionally well maintained. The lo-fi music playing throughout the property created the perfect zen atmosphere. The location was ideal: close to El Yunque, beaches, restaurants, and everything we wanted to explore, yet secluded enough to feel peaceful and private. We loved spending our time by the pool, reading, and simply enjoying the serenity. It’s truly perfect for adults looking to relax and disconnect. The kitchen was fully equipped with everything we needed, and the recommendations provided by the property were a wonderful touch. We followed their beach recommendation and visited San Miguel Beach, a remote and absolutely fantastic beach that became one of the highlights of our trip. We were lucky enough to have the entire property to ourselves. Check-in was easy with the access code, and having the gate key made coming and going convenient. And the sweetest surprise? Meeting the neighbors’ two adorable Schnauzers! 🐶 They definitely made our stay even more memorable. Mata ‘e Platano truly feels like a little piece of heaven. If you’re visiting Fajardo and want a beautiful, serene escape close to everything but away from the crowds, don’t miss this place! We absolutely loved our stay and will definitely be back!"

Find out more about Roosevelt Roads

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Roosevelt Roads Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Roosevelt Roads vacation rentals

1. Mami Ana Beach House.10min ferry Vieques/Culebra. Beautifull, excelent location

2. The Ceiba Villa by Otium

3. Playa Colorá

4. Playa icacos

5. Wonderful 2-bedroom cottage with AC in charming Ceiba. Minutes from the Ferry.

6. Costa Brava Condo by Otium

7. Beautiful apartment in Fajardo

8. Villa Mango

9. El Yunque Rainforest

10. Charming and Private Stay in Fajardo - Near Ferry - Beaches - EL Yunque - Biobay

11. Colmado by Otium

12. Family friendly place for those looking for adventure, beach, and great food!

13. Casa Parcha

14. La Casita del Este

15. Playa palomino

16. Garden Suite near the Beach and restaurants!

17. Marina villa 3 bed 2-bathroom full kitchen equipped: electric generator

18. Luxury Penthouse w/ Ocean & Marina Views • Pool

19. Sea Breeze Escape | Sleeps 7 + Pool in Ceiba

20. Spacious 3 bedroom apartment with sea view short drive to Ceiba ferry station.

Find vacation rentals that suit your style

Top Roosevelt Roads Hotel Reviews

El Conquistador Resort

Find out more about Roosevelt Roads

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