
Roosevelt Roads Vacations from $505
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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
Save 100% on your flight
Price was $1,287, price is now $646 per person
$646
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (33 reviews)
I booked this place thinking it was in the heart of Old San Juan based on reviews about the “great location,” but it actually wasn’t close to much — about a 20-minute walk to the main attractions.
The front desk is technically available 24/7, but only through a messaging system, and someone comes over if there’s an issue. They do respond quickly. One girl that came over at one point was not friendly whatsoever as if I was inconveniencing her:
That setup made me feel a bit uneasy since there’s no on-site security, and the building felt empty even though other guests were staying there. Entry is by keypad into an empty lobby.
The elevator didn’t work, and the next day we didn’t have hot water (though it was eventually fixed, the water pressure stayed low). The shower had a modern design with only half a wall and no door, which caused the bathroom floor to flood.
On the positive side, the king bed room was spacious. However, overall, I wouldn’t recommend this place if you’re looking to really experience Old San Juan.
Reviewed on Aug 25, 2025

Urbana Hotel
San Juan Antiguo
Save 100% on your flight
Price was $1,212, price is now $619 per person
$619
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (328 reviews)
It's really nice since the bus stop is next to it (I rented a car but when I drop it I went back to
The hotel in the bus) was convenient, the staff are super friendly, easy going but the facilities seems not take care of and I request them to clean but they don't change the sheets/blankets and they didn't swip or mop, neither clean the zinc or the shower and also the shower doesn't have hot water
Reviewed on Aug 26, 2025
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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
$306 nightly
The price is $333 total per night from Aug 27 to Aug 28
$333 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (2,523 reviews)
"I absolutely loved my stay at this resort! I’ll definitely be booking with them again. The staff is so friendly and attentive, and there are so many fun things to do! Plus, the resort is really huge, which makes exploring it a great adventure!"
Reviewed on Aug 23, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard, Río Grande
$365 nightly
The price is $405 total per night from Aug 29 to Aug 30
$405 total
Aug 29 - Aug 30
Total with taxes and fees
8.4/10 Very Good! (2,146 reviews)
"Beautiful and the staff went above and beyond to help with everything."
Reviewed on Aug 25, 2025

El Conquistador Resort
1000 Conquistador Avenue, Fajardo
$344 nightly
The price is $375 total per night from Aug 27 to Aug 28
$375 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (3,170 reviews)
"Highly recommended"
Reviewed on Aug 25, 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.
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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.