
Roosevelt Roads Vacations from $410
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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 $845, price is now $410 per person
$410
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
Staff was awesome, room was clean. Breakfast was the same every day, omelette, sausage/hot dogs, yogurt, strong coffee, and juice. Outside of the building didn’t match photos on website or Expedia. There were no amenities, rooftop was closed, no spa, no hot tub. Great access to everything in San Juan. No restaurant on site, no laundry, not in a nature reserve it’s in the middle of San Juan. No sauna, no banquet hall, elevator was questionable. For the price it was a great stay, but if you need a hot tub or spa you’ll have to drive. Check in wasn’t on time, but we got a similar room after waiting a few hours. No golf course nearby!
We really enjoyed our stay water pressure and temperature was awesome!
Reviewed on Jan 3, 2026

Dorado Beach 5 Bedroom Villa
Higuillar
Save 100% on your flight
Price was $1,790, price is now $950 per person
$950
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (1 review)
Space, location, private accommodations, modern kitchen, washer dryer
Reviewed on Nov 27, 2025

The Oliver Hotel
San Juan Antiguo
Save 100% on your flight
Price was $962, price is now $529 per person
$529
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (50 reviews)
Definitely a different experience to not have a ton of amenities or staff on site at all times as they manage multiple properties. That being said, they were always a quick text or phone call away and everyone was extremely friendly and helpful. Great location and very clean room. I would definitely recommend this spot for the next traveler looking for a great (and walkable) place to stay near Old San Juan and/or Condado.
Reviewed on Jan 5, 2026


Aire de O:live
Isla Verde
Price was $1,178, price is now $710 per person
$710
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
There was an issue with my room for the first couple nights, but they remedied it and also gave me something that was really thoughtful in the new room. In addition to switching my room they also offered me a free breakfast while they try to fix the problem the first day that I stayed. I didn’t get to go to the second restaurant, but I did have food from there on the beach, which was a nice touch. Overall, I think I would come back and I would suggest this property to friends, family, and loved ones.
Reviewed on Jan 7, 2026
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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
$535 nightly
The price is $583 total per night from Jan 27 to Jan 28
$583 total
Jan 27 - Jan 28
Total with taxes and fees
8.8/10 Excellent! (2,859 reviews)
Everything was excellent
Reviewed on Jan 5, 2026

El Conquistador Resort
1000 Conquistador Avenue Fajardo
$414 nightly
The price is $451 total per night from Jan 15 to Jan 16
$451 total
Jan 15 - Jan 16
Total with taxes and fees
9/10 Wonderful! (3,225 reviews)
We had a wonderful time. Great New Year's Eve party!
Reviewed on Jan 5, 2026

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 Feb 5 to Feb 6
$948 total
Feb 5 - Feb 6
Total with taxes and fees
8.4/10 Very Good! (2,272 reviews)
Clean room, good service
Reviewed on Jan 5, 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.



















