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 Vacations

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Top Romantic vacation packages in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
  • Dec 30 - Jan 3

    Aura House Isla Verde + Flight

    Isla Verde
    4 nights
    3.0 star property
    7.8/10 - Good (419 reviews)
    "Stayed there for 5 days. Room was clean. Hot water was perfect. Jacuzzi upstairs was a plus and well needed. Unfortunately the temperature control was hard to use. Everything is in walking distance beach or food.I would definitely stay there again if need be."
    Reviewed November 9, 2026
    Roundtrip • Atlanta (ATL) - San Juan (SJU)
    ATL - SJU • Nonstop SJU - ATL • 1 stop
    ¥249,077
    ¥205,464
    per traveler
    found 1 day ago
    Aura House Isla Verde
  • Dec 30 - Jan 3

    THE BUOY + Flight

    Santurce
    4 nights
    3.5 star property
    9.6/10 - Exceptional (69 reviews)
    Roundtrip • Atlanta (ATL) - San Juan (SJU)
    ATL - SJU • Nonstop SJU - ATL • 1 stop
    ¥377,518
    ¥294,628
    per traveler
    found 1 day ago
    THE BUOY
  • Dec 30 - Jan 3

    Ocean Breeze Villa + Flight

    Puerta de Tierra
    4 nights
    4.0 star property
    9.2/10 - Wonderful (45 reviews)
    "Room was very clean and accessible to major parts I wanted to see in the city. No food or drink available and no conditioner in the shower. I didn't access the pool but the staff was kind."
    Reviewed November 10, 2026
    Roundtrip • Atlanta (ATL) - San Juan (SJU)
    ATL - SJU • Nonstop SJU - ATL • 1 stop
    ¥390,391
    ¥317,686
    per traveler
    found 1 day ago
    Ocean Breeze Villa
  • Dec 30 - Jan 3

    Hacienda Bello Sitio + Flight

    Mameyes I
    4 nights
    1.0 star property
    10/10 - Exceptional (4 reviews)
    "Such a nice and relaxing place to stay. Off the beaten path but not too far from Luquillo "
    Reviewed March 6, 2026
    Roundtrip • Atlanta (ATL) - San Juan (SJU)
    ATL - SJU • Nonstop SJU - ATL • 1 stop
    ¥255,565
    ¥208,693
    per traveler
    found 1 day ago
    Hacienda Bello Sitio
  • Dec 30 - Jan 3

    OLV Fifty Five - Adults Only + Flight

    Condado
    4 nights
    4.5 star property
    8.8/10 - Excellent (827 reviews)
    Roundtrip • Atlanta (ATL) - San Juan (SJU)
    ATL - SJU • Nonstop SJU - ATL • 1 stop
    ¥460,028
    ¥376,167
    per traveler
    found 1 day ago
    OLV Fifty Five - Adults Only

Discover the most popular places to visit in Roosevelt Roads

How to find a romantic Roosevelt Roads vacation

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Roosevelt Roads romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Roosevelt Roads?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Roosevelt Roads?

Put a price on love with stunning deals for duos starting at just ¥205,463. Prices and availability are subject to change. Additional terms may apply.

Can I book Roosevelt Roads spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Roosevelt Roads?

To book a loved-up break in Roosevelt Roads, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

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

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?