Roosevelt Roads Vacations from $325
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Roosevelt Roads vacation packages
Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
Condado
Price was $722, price is now $325 per person
$325
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
Great staff, chill vibe. Convenient location near restaurants and grocery store with adorable "shop cat" who hangs around for ear rubs and food.
Reviewed on Feb 6, 2026
Hotel Puerto Valdes
San Juan Antiguo
Price was $1,427, price is now $712 per person
$712
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (500 reviews)
Room was very clean, the staff was extremely nice and gave great suggestions for local restaurants, and no noise issues. Some of the equipment was out of service, but the staff were actively fixing the elevator and other devices in the morning
Reviewed on Feb 4, 2026
The Oliver Hotel
San Juan Antiguo
Save 100% on your flight
Price was $1,342, price is now $702 per person
$702
per person
Apr 19 - Apr 25
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 $1,260, price is now $701 per person
$701
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (389 reviews)
The room was very cute and clean and the staff amazing. Everything was walking distance and it felt so great to be back home.
Reviewed on Feb 6, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all tripsDiscover the most popular places to visit in Roosevelt Roads
Ceiba Ferry Terminal
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! (3,216 reviews)
Service, facility, room, amenities all wonderful! This is a great and beautiful hotel. The staff is kind and helful. We will be back soon.
Reviewed on Feb 2, 2026
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
$559 nightly
The price is $610 total per night from Feb 8 to Feb 9
$610 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (2,906 reviews)
We selected an ocean-view room with two double beds, which provided plenty of space for my wife, my son, and me. The location was beautiful, and the staff was absolutely incredible. There are several restaurants and shops on the property, though they are quite expensive. That said, nearly everything ...
Reviewed on Feb 5, 2026
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
$795 nightly
The price is $882 total per night from Mar 1 to Mar 2
$882 total
Mar 1 - Mar 2
Total with taxes and fees
8.4/10 Very Good! (2,242 reviews)
Wow... everything was perfect! The lobby, the staff, the rooms, the amenities, the layout, the kids' pool and adult pool, the clean beach, and perfect drinks! All of the staff from the casino, spa to bellman were extremely kind and caring. The restaurants were also wonderful! We will be back!
Reviewed on Feb 3, 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) |
More vacations you might like
Explore a world of travel with Expedia
- All-inclusive Resorts in Puerto Rico
- Condo Rentals in Aguas Claras
- Ceiba Hotels
- Guest Houses in Ceiba
- Condo Rentals in Ceiba
- Hostels in Ceiba
- Apartments in Ceiba
- Hilton Hotels in Ceiba
- Beach Hotels in Ceiba
- B&B in Ceiba
- Villas in Ceiba
- Cheap Hotels in Ceiba
- Resorts in Ceiba
- Cottages in Ceiba
- Luxury Hotels in Ceiba
- Hotels with a Pool in Ceiba
- Hotels with Free Breakfast in Ceiba
- 4 Star Hotels in Ceiba
- Vacation Homes in Ceiba
- Hotels with Restaurants in Ceiba
- Romantic Hotels in Ceiba
- Hotels near Ceiba Ferry Terminal
- Hotels near Splash Tattoo
- Apartments in Daguao
- Daguao Hotels
- Hotels near Diego Jimenez Torres
- Fajardo Hotels
- Naguabo Hotels
- Flights to Puerto Rico Island
- Flights to Aguas Claras
- Flights to Ceiba
- Flights from Ceiba
- Flights from San Juan (SJU) to Fajardo (FAJ)
- Flights from Diego Jimenez Torres
- Flights from New York (NYC) to Fajardo (FAJ)
- Flights from Culebra (CPX) to Fajardo (FAJ)
- Flights from New York (JFK) to Fajardo (FAJ)
- Flights from Boston (BOS) to Fajardo (FAJ)
- Flights from Philadelphia (PHL) to Fajardo (FAJ)
- Flights from St. Thomas (STT) to Fajardo (FAJ)
- Flights from Miami (MIA) to Fajardo (FAJ)
- Flights from Orlando (MCO) to Fajardo (FAJ)
- Flights from Tampa (TPA) to Fajardo (FAJ)
- Flights from Chicago (CHI) to Fajardo (FAJ)
- Flights from Los Angeles (LAX) to Fajardo (FAJ)
- Flights from Washington (DCA) to Fajardo (FAJ)
- Flights from Houston (HOU) to Fajardo (FAJ)
- Flights from Atlanta (ATL) to Fajardo (FAJ)
- Flights from Hartford (BDL) to Fajardo (FAJ)
- Flights from Denver (DEN) to Fajardo (FAJ)
- Flights from Fort Lauderdale (FLL) to Fajardo (FAJ)
- Flights from Raleigh (RDU) to Fajardo (FAJ)
- Flights from Vieques (VQS) to Fajardo (FAJ)
- Flights from San Francisco (SFO) to Fajardo (FAJ)
- Flights from Pittsburgh (PIT) to Fajardo (FAJ)
- Flights from Charlotte (CLT) to Fajardo (FAJ)
- Flights from Columbus (CMH) to Fajardo (FAJ)
- Flights from Norfolk (ORF) to Fajardo (FAJ)
- Flights from Las Vegas (LAS) to Fajardo (FAJ)
- Flights from London (LON) to Fajardo (FAJ)
- Flights from Richmond (RIC) to Fajardo (FAJ)
- Flights from San Antonio (SAT) to Fajardo (FAJ)
- Flights from Detroit (DTW) to Fajardo (FAJ)
- Flights from Mayagüez (MAZ) to Fajardo (FAJ)
- Flights from San Juan (SIG) to Fajardo (FAJ)
- Flights from Seattle (SEA) to Fajardo (FAJ)
- Flights from Dallas (DFW) to Fajardo (FAJ)
- Flights to Naguabo
- Car rentals near Aguas Claras
- Car rentals near Ceiba
- Car rentals near Ceiba Ferry Terminal
- Enterprise Rental Cars in Ceiba
- Avis Rental Cars in Ceiba
- Hertz Rental Cars in Ceiba
- Thrifty Car Rental Rental Cars in Ceiba
- Alamo Rent A Car Rental Cars in Ceiba
- Budget Rental Cars in Ceiba
- Payless Rental Cars in Ceiba
- Priceless Car Rental Rental Cars in Ceiba
- Car rentals near Saco
- Car rental San Juan Airport (FAJ)
- Car rentals near Naguabo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
