Roosevelt Roads Vacations from $278
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The Latest Roosevelt Roads vacation packages
Price found within the past 48 hours. Click for updated prices.
The Oliver Hotel
San Juan Antiguo
Price was $1,077, price is now $517 per person
$517
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (50 reviews)
Great location to San Juan Old town. Hotel staff very helpful and room a nice size and clean.
Had 2 night here before a cruise and would certainly recommend it.
Reviewed on Feb 2, 2026
Urbana Hotel
San Juan Antiguo
Save 100% on your flight
Price was $1,018, price is now $542 per person
$542
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (389 reviews)
First receptionist was sort of rude maybe is their culture. But the worse was the room my closest is bigger one small night stand, no room for even the suitcase. What really bothered me all the rules they place on the room. Can’t use washcloths to clean face gave us two small packets to wipe face but were dry or get charge $35, can’t flush paper on toilet get fine to unclog, there were so many rules but the worse was the room look like they were doing construction on it. Not happy at all. The room was $210 per night.
Reviewed on Feb 8, 2026
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Ceiba Ferry Terminal
3.5/5(109 reviews)
Explore the waterfront in Machos with a trip to Ceiba Ferry Terminal.
Roosevelt Roads Hotel Deals
El Conquistador Resort
1000 Conquistador Avenue Fajardo
$434 nightly
The price is $473 total per night from Mar 1 to Mar 2
$473 total
Mar 1 - Mar 2
Total with taxes and fees
9/10 Wonderful! (3,218 reviews)
The room was spotless and the views were amazing. The staff was beyond friendly. We had the most fabulous time and will return!
Reviewed on Feb 4, 2026
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
$464 nightly
The price is $505 total per night from Feb 12 to Feb 13
$505 total
Feb 12 - Feb 13
Total with taxes and fees
9/10 Wonderful! (2,919 reviews)
Room was beautiful
Reviewed on Feb 7, 2026
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
$778 nightly
The price is $864 total per night from Feb 17 to Feb 18
$864 total
Feb 17 - Feb 18
Total with taxes and fees
8.4/10 Very Good! (2,247 reviews)
Rooms were nicely updated the staff was friendly and service was good Golf courses were subpar, without the rain they were average but with the rain unplayable.
Reviewed on Feb 10, 2026
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.
Find the Best Roosevelt Roads Vacation Packages
Roosevelt Roads Essential Information
Language | Spanish |
|---|---|
Currency | U.S dollars |
Local Welcome | ¡Hola! |
Local Goodbye | Adiós |
Closest Airport | Luis Munoz Marin Intl. Airport (SJU) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
