Roosevelt Roads Beach Vacations 2026

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Top Beach vacation packages in Roosevelt Roads

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

Ola Boutique Hotel

Condado

$693

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9/10 Wonderful! (989 reviews)

Hotel Puerto Valdes

San Juan Antiguo

Save 100% on your flight

$824

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

8.8/10 Excellent! (748 reviews)

Very helpful and happy staff.

Reviewed on Oct 4, 2026

SELVA by DW

Pitahaya

Save 100% on your flight

$1,484

per person

Dec 7 - Dec 10

found 17 hours ago

Roundtrip flight included

Philadelphia (PHL) to San Juan (SJU)

10/10 Exceptional! (3 reviews)

Todo estuvo perfecto limpieza 💯communication al 💯 y los servicios ofrecido todo me parecio exelente buen olor en las toallas y sabanas ,

Reviewed on Jun 25, 2026

Signature Collection at Rio Mar

Mameyes II

Save 100% on your flight

$3,380

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

6/10 (1 review)

Everything is 10 times more expensive compare to any other place I visites

Reviewed on Aug 8, 2026

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

Save 100% on your flight

$1,031

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.2/10 Wonderful! (3,451 reviews)

Absolutely beautiful property, well maintained and friendly staff. Will definitely plan another stay.

Reviewed on Oct 6, 2026

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5* Beach vacations in Roosevelt Roads

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

Fairmont El San Juan Hotel

Isla Verde

Save 100% on your flight

$1,466

per person

Dec 21 - Dec 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

8.6/10 Excellent! (2,233 reviews)

Room was nasty had ants and blood . When I complained to staff the front desk lady just responded with “you do realize you’re in a island”

Reviewed on Oct 7, 2026

Signature Collection at Rio Mar

Mameyes II

Save 100% on your flight

$3,380

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

6/10 (1 review)

Everything is 10 times more expensive compare to any other place I visites

Reviewed on Aug 8, 2026

Fairmont El San Juan Villa Experience

Isla Verde

Save 100% on your flight

$1,515

per person

Dec 21 - Dec 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

7.8/10 Good! (158 reviews)

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3 Night Beach vacations in Roosevelt Roads

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

Hotel Puerto Valdes

San Juan Antiguo

Save 100% on your flight

$649

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to San Juan (SJU)

8.8/10 Excellent! (748 reviews)

Very helpful and happy staff.

Reviewed on Oct 4, 2026

Ola Boutique Hotel

Condado

Save 100% on your flight

$714

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to San Juan (SJU)

9/10 Wonderful! (989 reviews)

Signature Collection at Rio Mar

Mameyes II

Save 100% on your flight

$4,547

per person

Dec 31 - Jan 3

found 23 hours ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

6/10 (1 review)

Everything is 10 times more expensive compare to any other place I visites

Reviewed on Aug 8, 2026

Don't see what you're looking for?

See all available trips from Columbus to Roosevelt Roads

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4 Night Beach vacations in Roosevelt Roads

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

Ola Boutique Hotel

Condado

$693

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9/10 Wonderful! (989 reviews)

Hotel Puerto Valdes

San Juan Antiguo

Save 100% on your flight

$824

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

8.8/10 Excellent! (748 reviews)

Very helpful and happy staff.

Reviewed on Oct 4, 2026

WALD HAUS by DW

Save 100% on your flight

$1,910

per person

Dec 12 - Dec 16

found 21 hours ago

Roundtrip flight included

Philadelphia (PHL) to San Juan (SJU)

9.2/10 Wonderful! (11 reviews)

The home itself is absolutely stunning but the road to the villa is not just narrow, it's washed out in many places, we struggled to navigate the potholes even with a jeep and an SUV, I would not drive it at night. There are great amenities like the fridge and bathroom downstairs, the coffee / cocktail bar is fabulous.The kitchen was well-stocked with basic spices and supplies but it was crawling with roaches. Wifi is spotty so be sure to have the guidebook downloaded and screenshots of the phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.

Reviewed on Aug 13, 2026

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How do I book the best Roosevelt Roads beach vacation packages?

Life’s a beach when you dive into our brilliant Roosevelt Roads beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Roosevelt Roads?

A rental steps from the shore creates an amazingly affordable Roosevelt Roads beach vacation. Seaside sojourns during low season start from $649. Prices and availability are subject to change. Additional terms may apply.

When should I book a Roosevelt Roads beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

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

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Roosevelt Roads beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Roosevelt Roads vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Roosevelt Roads beach vacation deals?

Sort your search results by deals to delight in amazing Roosevelt Roads beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Roosevelt Roads beach trip with free cancellation and/or flexible dates?

Just like the Roosevelt Roads tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Roosevelt Roads beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Roosevelt Roads. (OK, maybe not that last part.)

Top Beach Roosevelt Roads Hotels

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

Ceiba Puerto rico

9 min drive from Ceiba Ferry Terminal

Stroll along the shoreline in Ceiba, as you'll be a short walk from the beach with a stay at this villa.

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

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.