
Roosevelt Roads Vacations from $389
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The Latest Roosevelt Roads vacation packages
Price found within the past 48 hours. Click for updated prices.

Lazy Parrot Inn
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (1,001 reviews)
The staff was so nice and friendly. The staff spoke English which helped with my language barrier. Everyone was attentive and willing to help when we needed something.
Reviewed on Aug 11, 2025

San Agustin Apartments
San Juan Antiguo
per person
Oct 18 - Oct 25
found 2 days ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (370 reviews)
I have nothing to complain about the customer service. The people working made it very welcoming and offered to help bring our luggage to our rental when we checked out, as well as help us with unclean sheets that we discovered. There was hair that did not belong to us on the bed when se first arrived and the fitted bed sheet that covered the mattress underneath had a big yellow stain that smelled of fish. we talked to the concierge and they were qui k to send someone to change the sheets with new linen. there was some stains on the wall in thr bathroom and on our bedroo
wall, but for only staying 3 days we ignored the stains and kept it going. the view outside the apartment wasnt anything special, but it wasnt horrible.
Reviewed on Aug 12, 2025

Urbana Hotel
San Juan Antiguo
Save 100% on your flight
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (317 reviews)
Great little property. They have hotels next door part of the same company, great little store down the street that has everything down the street.
Reviewed on Aug 10, 2025


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Ceiba Ferry Terminal
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
$306 nightly
The price is $333 total per night from Sep 2 to Sep 3
$333 total
Sep 2 - Sep 3
Total includes taxes and fees
8.8/10 Excellent! (2,461 reviews)
"Great Property."
Reviewed on Aug 11, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard, Río Grande
Fully refundableReserve now, pay when you stay
$316 nightly
The price is $351 total per night from Sep 2 to Sep 3
$351 total
Sep 2 - Sep 3
Total includes taxes and fees
8.6/10 Excellent! (2,115 reviews)
"The facility was absolutely beautiful! Our room was clean and comfortable, food was great, we ate from the tiki bar and the restaurants and we enjoyed everything."
Reviewed on Aug 11, 2025

El Conquistador Resort
1000 Conquistador Avenue, Fajardo
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $429 total per night from Aug 24 to Aug 25
$429 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (3,131 reviews)
"Our summer family vacation at El Conquistador was truly unforgettable! As first-time visitors to Puerto Rico, we couldn’t have chosen a better place. The property is perfect for families, offering everything you need to keep everyone entertained—delicious restaurants, fun activities, and amazing ..."
Reviewed on Aug 10, 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.