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 Adults Only Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Adults Only vacation packages in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
  • Jan 20 - Jan 26

    THE BUOY + Flight

    Santurce
    6 nights
    3.5 star property
    9.6/10 - Exceptional (69 reviews)
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $2,068
    CA $1,350
    per traveller
    found 1 day ago
    THE BUOY
  • Jan 29 - Feb 3

    Hotel Puerto Valdes + Flight

    Puerta de Tierra
    5 nights
    4.0 star property
    8.8/10 - Excellent (765 reviews)
    "Staff was excellent and very helpful during our stay especially Hector. Unfortunately the shuttle has been out of service and the hot tub needed cleaning. There were several other issues we encountered that were rectified by the Hector as well as other staff members at the time of need."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    Save 100% on your flight
    CA $2,937
    CA $1,726
    per traveller
    found 1 day ago
    Hotel Puerto Valdes
  • Dec 17 - Dec 22

    Hyatt Regency Grand Reserve Puerto Rico + Flight

    Zarzal
    5 nights
    4.0 star property
    9.2/10 - Wonderful (3,532 reviews)
    "My two sisters and I came to this property for a long weekend to celebrate my sister's birthday! It was truly a wonderful stay. Our oceanfront room was spacious with a beautiful view. The staff were attentive and helpful with all of our questions. We took advantage of the spa for massages, participated in a yoga session, and utilized the complimentary bikes for a ride around the property. All weekend, we were plotting how to bring the rest of our families to enjoy the resort in the future! ..."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 2 stops SJU - YYZ • 1 stop
    Save 100% on your flight
    CA $3,334
    CA $2,178
    per traveller
    found 1 day ago
    Hyatt Regency Grand Reserve Puerto Rico
  • Jan 20 - Jan 26

    Isla Verde Beachfront ESJ Tower by Otium + Flight

    Isla Verde
    6 nights
    2.0 star property
    9.6/10 - Exceptional (7 reviews)
    "Nice stay and the staff was nice"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $2,860
    CA $1,875
    per traveller
    found 1 day ago
    Isla Verde Beachfront ESJ Tower by Otium
  • Jan 20 - Jan 26

    Casa Elena by Otium + Flight

    Santurce
    6 nights
    3.0 star property
    8.6/10 - Excellent (39 reviews)
    "The biggest problem is that the windows do not have glass panes; they only have screens. As a result, whenever the blinds are opened, all the heat and humidity from outside enter the apartment. This makes it difficult to keep the apartment comfortable and well ventilated. In practice, the apartment has to remain dark because opening the blinds to let in natural light also allows a significant amount of heat and humidity to enter. The appartment is confortable, clean, well located and with easy..."
    Reviewed September 12, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $3,059
    CA $2,032
    per traveller
    found 1 day ago
    Casa Elena by Otium

Discover the most popular places to visit in Roosevelt Roads

Top Adults Only 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.

Frequently Asked Questions

How much does a Roosevelt Roads vacation package cost?

Be ready to book, because a getaway to Roosevelt Roads starts from an affordable CA $1,350. When you bundle your flights, hotels and car rentals into a package, you'll pick up the biggest bargains.

How do I get a cheap travel package to Roosevelt Roads?

Imagine all the wonderful things you could do in Roosevelt Roads with a wad of extra cash in your wallet. Watch your savings stack up when you combine your flights and hotel into a Roosevelt Roads vacation package. You have loads of choice when it comes to booking with Expedia too. In fact, you can pick from over 550 airlines and 1,000,000 hotel options throughout the world. Whether you're taking a vacation with the whole family or traveling with someone special, organizing a trip to Roosevelt Roads is better with a package.

What are the top hotels in Roosevelt Roads?

People traveling to Roosevelt Roads often book Vistaazulpenthouse or Cbrava Apartment With Ocean View/ Pool. You'll find them in Machos. Another interesting neighborhood is Guayacán. Exclusive Villas, Hidden Paradise Near Beaches and Escape Half The World are well-liked options in this part of town.

How far in advance should I book my Roosevelt Roads vacation?

Savvy travelers often book early. You can generally compare international airfares on Expedia up to a year before your intended flight. If you're late to book, there's no need to worry. Discounted prices occasionally occur just weeks before departure.

What does an Expedia Roosevelt Roads travel package include?

It all comes down to what type of trip you're thinking about. Roosevelt Roads vacation deals can include hotels, car rentals and flights. You can mix and match to find the travel package that suits you. You can also add on experiences and activities after you've booked to pick up even bigger discounts.

What should I know before booking a Roosevelt Roads travel package?

Locking in all the parts of your vacation together is a simple way to save. Combine your airfares, rental cars and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including vacation rentals like oceanfront condos and short-term homes. You've got loads of choices!

Can I choose my airline with a Roosevelt Roads Expedia vacation package?

Yes, so take your pick! Expedia has access to more than 550 airlines throughout the world, so you can customize your Roosevelt Roads adventure according to your needs and budget.

If I'm not able to travel, can I cancel my Roosevelt Roads vacation package?

It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Roosevelt Roads vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.