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.
  • Sept 20 - Sept 26

    Hotel Puerto Valdes + Flight

    Puerta de Tierra
    6 nights
    4.0 star property
    8.8/10 - Excellent (713 reviews)
    "Our stay there was great! It was walking distance to old San Juan. The hotel was beautiful and the staff was friendly. The only downside was, the hot tub didn’t work and there was no warm water. I would stay here again."
    Reviewed August 5, 2026
    Roundtrip Toronto (YTO) - San Juan (SJU)
    YYZ - SJU1 stop SJU - YYZ1 stop
    CA $1,912
    CA $1,241
    per traveller
    found 1 day ago
    Hotel Puerto Valdes
  • Oct 13 - Oct 18

    Isla Verde Beachfront Retreat With Parking + Flight

    Isla Verde
    5 nights
    2.0 star property
    10/10 - Exceptional (2 reviews)
    "Good location, nice place, clean, looks the sana as pictured. Walking distance to the beach, restaurants and casino. Doesn’t have pool."
    Reviewed July 21, 2026
    Roundtrip Toronto (YTO) - San Juan (SJU)
    YYZ - SJU1 stop SJU - YYZ1 stop
    CA $2,662
    CA $1,394
    per traveller
    found 2 days ago
    Isla Verde Beachfront Retreat With Parking
  • Oct 18 - Oct 24

    PAZ by DW + Flight

    Santurce
    6 nights
    4.5 star property
    9.0/10 - Wonderful (26 reviews)
    "Great location! "
    Reviewed April 7, 2026
    Roundtrip Toronto (YYZ) - San Juan (SJU)
    YYZ - SJU1 stop SJU - YYZ1 stop
    CA $1,941
    CA $1,354
    per traveller
    found 1 day ago
    PAZ by DW
  • Oct 18 - Oct 24

    WALD HAUS by DW + Flight

    Naguabo
    6 nights
    4.0 star property
    9.8/10 - Exceptional (10 reviews)
    Roundtrip Toronto (YYZ) - San Juan (SJU)
    YYZ - SJU1 stop SJU - YYZ1 stop
    CA $5,272
    CA $3,708
    per traveller
    found 1 day ago
    WALD HAUS by DW
  • Oct 16 - Oct 21

    VILLA JOYUDA + Flight

    Cabo Rojo
    5 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "It has everything you may need and more"
    Reviewed November 5, 2025
    Roundtrip Montreal (YUL) - San Juan (SJU)
    YUL - SJU1 stop SJU - YUL1 stop
    CA $7,615
    CA $5,374
    per traveller
    found 18 hours ago
    VILLA JOYUDA

Top Romantic Roosevelt Roads Hotels

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.

Plan unforgettable romantic Roosevelt Roads vacations

What are some of the benefits of booking a romantic Roosevelt Roads vacation?

When booking a romantic Roosevelt Roads vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Puerto Rico.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Roosevelt Roads destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Roosevelt Roads?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,241 and can enjoy savings of up to 35 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Roosevelt Roads?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Roosevelt Roads certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Roosevelt Roads.

Can I book a romantic Roosevelt Roads vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Roosevelt Roads search.

Can I book a romantic trip to Roosevelt Roads that is fully refundable?

Several romantic Roosevelt Roads vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.