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 Romantic Holidays

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Top Romantic holiday packages in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
  • 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
  • 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
  • 19 Dec - 26 Dec

    Hyatt Vacation Club at Hacienda del Mar, Dorado + Flight

    Sabana
    6 nights
    3.5 star property
    9.4/10 - Exceptional (4,215 reviews)
    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
  • 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
  • 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

How to find a romantic Roosevelt Roads holiday

How can I find the best Roosevelt Roads vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Roosevelt Roads. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Roosevelt Roads romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Roosevelt Roads that start from £1,380. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Roosevelt Roads romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Roosevelt Roads?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Roosevelt Roads?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Roosevelt Roads that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

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

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Roosevelt Roads romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.