Roosevelt Roads Beach Holidays

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Top flight + Beach hotel deals in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
310Guest-House LaVida

310Guest-House LaVida

Old San Juan
AU$1,825
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
9.2/10 Wonderful! (55 reviews)
Hotel Puerto Valdes

Hotel Puerto Valdes

Puerta de Tierra
AU$2,146
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
8.8/10 Excellent! (710 reviews)
I really enjoyed my stay, and the staff made us feel welcomed.

Reviewed on 7 Aug 2026

Caribe Hilton

Caribe Hilton

Puerta de Tierra
AU$2,278
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
8.6/10 Excellent! (2,987 reviews)
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

Old San Juan
AU$1,916
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
9/10 Wonderful! (1,815 reviews)
Clean room Nice staff Great food Great customer service Awesome location

Reviewed on 9 Aug 2026

Hugo's Rental

Hugo's Rental

Old San Juan
AU$1,909
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
9.2/10 Wonderful! (339 reviews)
I have stayed at this hotel previously without any issues. This stay was not the same. As I walked in the room you could smell mold. I have allergies and this made it unbearable. It was so bad I had to sleep with a mask.

Reviewed on 21 June 2026

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5* Beach holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Hugo's Rental

Hugo's Rental

Old San Juan
AU$1,909
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
9.2/10 Wonderful! (339 reviews)
I have stayed at this hotel previously without any issues. This stay was not the same. As I walked in the room you could smell mold. I have allergies and this made it unbearable. It was so bad I had to sleep with a mask.

Reviewed on 21 June 2026

Residences at Dorado Beach, a Ritz-Carlton Reserve

Residences at Dorado Beach, a Ritz-Carlton Reserve

Higuillar
Save 100% on your flight
AU$21,525
per person
16 Sept - 22 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans.

Reviewed on 1 Sept 2025

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What is a Roosevelt Roads beach holiday package and why choose one?

How can I book a Roosevelt Roads beach holiday package with Expedia?

Beach holidays to beach holidays on Expedia?

To find your ideal family-friendly Roosevelt Roads beach holiday package, simply use the site’s or the app’s search function to explore diverse packages tailored to your chosen destination. Refine your search with filters to narrow down options based on your favourite amenities.

How can I select the perfect beach holiday package for Roosevelt Roads?

Customise your quest for Roosevelt Roads beach holiday packages, including flights, with search filters and prioritise your preferred options. This way, you’ll uncover fantastic beach holidays, whether it’s a romantic beach escape, a luxurious beach package, or a surfers’ paradise in Roosevelt Roads.

How can I find the best Roosevelt Roads beach holiday deals?

Grab some of the best Roosevelt Roads beach holiday deals by being flexible with your destination and dates, ideally travelling outside of peak seasons. If you have specific seas in mind, enter the details and apply filters to uncover a budget-friendly trip.

How can I discover last-minute Roosevelt Roads beach holiday deals?

If you love a last-minute deal, you’ve come to the right place. Select our top picks or customise your beach getaway in Roosevelt Roads using date and destination filters. Bundle accommodation, airfare, and car rental for the best value. Tailor your search with filters covering amenities, price, star rating, and more.

How can I find pet-friendly Roosevelt Roads beach holiday packages?

Indulge yourself and your furry companion in Roosevelt Roads’s pet-friendly beach holiday options. Enhance your getaway with our filters, including doggy day care, divine pet-friendly beach apartments, and access to pet-friendly local beaches.

When are the best times to go for a Roosevelt Roads beach holiday?

For the ultimate Roosevelt Roads beach holiday, choose summer for vibrant energy. Alternatively, opt for winter to enjoy a tranquil, less crowded experience with ample alone time.

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