An aerial view of a tropical island with clear turquoise waters and a sandy beach.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Roosevelt Roads Luxury Holidays

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Top Luxury holiday packages in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
  • A modern hotel room with a large bed, a bathroom with a glass shower, and a view of the city.
    19 Dec - 26 Dec

    Hotel Las Vegas + Flight

    Santa Isabel
    6 nights
    3.0 star property
    8.2/10 - Very good (399 reviews)
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £1,439
    £1,380
    per traveller
    found 1 day ago
    Hotel Las Vegas
  • A modern bedroom with a large bed, a wooden nightstand, a wall-mounted TV, and a potted plant.
    19 Dec - 26 Dec

    La Calma Poshtel + Flight

    Santurce
    6 nights
    2.0 star property
    7.2/10 - Good (912 reviews)
    "The room was clean. The door to my room had been tampered with, I reached out to the owner and there was something’s missing from my room. They had stated that it was the housekeeper but that did not make sense to me as they should have the key/code. I ended my stay a few days earlier because I did not feel safe in that area, which I do let the rental company know."
    Reviewed November 10, 2026
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £1,524
    £1,384
    per traveller
    found 1 day ago
    La Calma Poshtel
  • A resort with a large pool, palm trees, and a view of the ocean.
    19 Dec - 26 Dec

    Hyatt Vacation Club at Hacienda del Mar, Dorado + Flight

    Sabana
    6 nights
    3.5 star property
    9.4/10 - Exceptional (4,214 reviews)
    "Beautiful stay!!!wish the food was better."
    Reviewed November 10, 2026
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £2,129
    £1,990
    per traveller
    found 1 day ago
    Hyatt Vacation Club at Hacienda del Mar, Dorado
  • A vibrant interior with yellow walls, a staircase, and a colorful couch with a glass table.
    19 Dec - 26 Dec

    The Fox Hotel + Flight

    Ponce Centro
    6 nights
    3.5 star property
    7.2/10 - Good (1,008 reviews)
    "The hot water never works, the sheets and fitted were dirty."
    Reviewed November 10, 2026
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £1,526
    £1,441
    per traveller
    found 1 day ago
    The Fox Hotel
  • A modern hotel room with two beds, a desk, and a flat-screen TV.
    19 Dec - 26 Dec

    Douglas Highway Hotel + Flight

    Cabo Rojo
    6 nights
    2.0 star property
    8.6/10 - Excellent (451 reviews)
    Return • London (LHR) - San Juan (SJU)
    LHR - PUJ • 1 stop PUJ - LHR • 1 stop
    £1,507
    £1,442
    per traveller
    found 1 day ago
    Douglas Highway Hotel

Discover the most popular places to visit in Roosevelt Roads

Playa Blanca

6.6/10 (4 reviews)
Why not spend a lazy afternoon at Playa Blanca during your trip to Guayacán?
See properties

All you need to know about luxury holidays in Roosevelt Roads

What can I expect from a luxury Roosevelt Roads holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Roosevelt Roads?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Roosevelt Roads holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Roosevelt Roads?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Roosevelt Roads starting at £1,380. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Roosevelt Roads?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Roosevelt Roads spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Roosevelt Roads?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Roosevelt Roads?

You can wangle a top-notch luxury holiday in Roosevelt Roads for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Roosevelt Roads with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Roosevelt Roads with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Roosevelt Roads to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.