Roosevelt Roads Beach Vacations

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Flight and Beach hotel deals in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel

Ola Boutique Hotel

Condado
Save 100% on your flight
CA $1,240
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (989 reviews)
Hotel Puerto Valdes

Hotel Puerto Valdes

San Juan Antiguo
Save 100% on your flight
CA $1,274
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (748 reviews)
Very helpful and happy staff.

Reviewed on Oct 4, 2026

Fairmont El San Juan Villa Experience

Fairmont El San Juan Villa Experience

Isla Verde
Save 100% on your flight
CA $2,907
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
7.8/10 Good! (158 reviews)
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

Zarzal
CA $2,354
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (3,451 reviews)
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
CA $2,388
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (2,233 reviews)
Night life music

Reviewed on Oct 7, 2026

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5* Beach holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
CA $2,388
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (2,233 reviews)
Night life music

Reviewed on Oct 7, 2026

Fairmont El San Juan Villa Experience

Fairmont El San Juan Villa Experience

Isla Verde
Save 100% on your flight
CA $2,907
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
7.8/10 Good! (158 reviews)
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
CA $2,724
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Juan (SJU)
9.4/10 Exceptional! (1,856 reviews)
Good

Reviewed on Oct 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
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3 Night Beach holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
610atMiramar

610atMiramar

Santurce
CA $693
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
8.4/10 Very good! (99 reviews)
The neighborhood has everything walking distance, however the room itself was not soundproof. I had a call with a relative, some young travelers were outside talking and my cousin said it sounds like they're in my room. Parking is difficult, so I wouldn't book a car if I'm staying here. The room has the a.c. on before I came in which I loved, tv had many options Room was clean

Reviewed on Aug 5, 2026

Ola Boutique Hotel

Ola Boutique Hotel

Condado
CA $941
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (989 reviews)
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

Zarzal
CA $2,491
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (3,451 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
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4 Night Beach holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Casa Ciana

Casa Ciana

Santurce
CA $1,229
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.6/10 Exceptional! (522 reviews)
Hotel Puerto Valdes

Hotel Puerto Valdes

San Juan Antiguo
Save 100% on your flight
CA $1,274
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (748 reviews)
Very helpful and happy staff.

Reviewed on Oct 4, 2026

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
CA $1,542
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (2,233 reviews)
Night life music

Reviewed on Oct 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
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Find the best beach vacations in Roosevelt Roads

What are some benefits when booking beach vacations in Roosevelt Roads?

When you travel to the beach in Roosevelt Roads, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Roosevelt Roads?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Roosevelt Roads trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Roosevelt Roads?

There are quite a few things you can do to get cheap beach vacations in Roosevelt Roads. Prices range from CA $693, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Roosevelt Roads. These package deals let you save by booking your accommodation and your flight together with savings of up to 50.

Why should I book family beach vacations?

When you're travelling with the family to Roosevelt Roads, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Roosevelt Roads?

It's easy to find a beachfront vacation accommodation in Roosevelt Roads using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Roosevelt Roads as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Roosevelt Roads is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Puerto Rico. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Roosevelt Roads

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

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

Ceiba Puerto rico
  • 9 min drive from Ceiba Ferry Terminal
Book a stay at this beach villa in Ceiba. Enjoy free WiFi, a beach locale, and patios. Popular attractions Ceiba Ferry Terminal and El Conquistador Golf Course ...
8/10 Very good! (6 reviews)
"The house was beautiful but it was way overpriced for how difficult it was to find it and get to it. It also smells terrible there because of the sarragassum. We were notified a couple days in advance of how bad it smelled but you could tell that there was weeks of horribly smelly sarragassum rotting ..."

Reviewed on Aug 1, 2026

Mami Ana Beach House.10min ferry Vieques/Culebra. Beautifull, excelent location
See all 2,285 properties in Roosevelt Roads
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.