Roosevelt Roads Vacations from $504
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The Latest Roosevelt Roads vacation packages
Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
Condado
Price was $2,123, price is now $842 per person
$842
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
From check-in to check out was flawless! The staff was more than accommodating. The location is perfect.Grocery store right across the street and ocean a block away.
The owner and staff were attentive in every way. 12 out of 10!!!! We cannot wait to come back to Ola Boutique!!!
They showed us all the good spots to go and even took us on a day with their family across the island we will never forget...!!!!!
Reviewed on Dec 22, 2025
The Oliver Hotel
San Juan Antiguo
Save 100% on your flight
Price was $1,189, price is now $591 per person
$591
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (50 reviews)
Nothing really close by, no front staff ever on site to help with local restaurants etc no stores nearby have to Uber everywhere. Rooms have no windows no water , ice machines etc..
Reviewed on Dec 14, 2025
Hotel Puerto Valdes
San Juan Antiguo
Save 100% on your flight
Price was $1,299, price is now $694 per person
$694
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (500 reviews)
great room and restaurant for dinner. Would of been five stars if they provided breakfast
Reviewed on Dec 23, 2025
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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
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
$531 nightly
The price is $579 total per night from Jan 13 to Jan 14
$579 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
9/10 Wonderful! (2,828 reviews)
Great overall
Reviewed on Dec 21, 2025
El Conquistador Resort
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
$414 nightly
The price is $451 total per night from Jan 7 to Jan 8
$451 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9/10 Wonderful! (3,202 reviews)
Clean room, nice beach and food. Expensive food
Reviewed on Dec 23, 2025
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
$854 nightly
The price is $948 total per night from Jan 5 to Jan 6
$948 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.4/10 Very Good! (2,244 reviews)
Excellent hotel, great location and the staff was super friendly.
Reviewed on Dec 22, 2025
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.
