Roosevelt Roads Vacations from $617
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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.
Lazy Parrot Inn
Save 100% on your flight
Price was $1,153, price is now $617 per person
$617
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (1,000 reviews)
We loved our stay here. The pool area was beautiful and had a hot tub as well. There was a game room and shelf with books for kids. Very family friendly. The place was very clean and had a coffee bar area set up in the morning. There was a gift shop and restaurant. Overall we loved it here. One thing to note was a very loud rooster very early in the morning. If they could get rid of the rooster it would be perfect haha.
Reviewed on Jul 14, 2026
THE BUOY
Santurce
Save 100% on your flight
Price was $1,320, price is now $778 per person
$778
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.6/10 Exceptional! (57 reviews)
We had a great stay and really like the location. We got a prompt response when our stovetop wasn’t working. The staff graciously moved us to another apartment so they could fix the problem. We would stay again.
Reviewed on Jun 30, 2026
Hotel Puerto Valdes
San Juan Antiguo
Save 100% on your flight
Price was $1,453, price is now $878 per person
$878
per person
Aug 20 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (686 reviews)
We had an EXCELLENT stay. The property is very conveniently located to everything in Old San Juan. It was a very quiet street. The staff was so friendly & helpful. The restaurant upstairs was great. We also loved the rooftop view. Would highly recommend & would absolutely stay here again!!
Reviewed on Jul 14, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all tripsStay near popular Roosevelt Roads attractions
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
$329 nightly
The price is $359 total per night from Aug 10 to Aug 11
$359 total
Aug 10 - Aug 11
Total with taxes and fees
9/10 Wonderful! (3,073 reviews)
"It was a good stay but make sure you bring your card with you."
Reviewed on Jul 14, 2026
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
$446 nightly
The price is $496 total per night from Aug 3 to Aug 4
$496 total
Aug 3 - Aug 4
Total with taxes and fees
8.6/10 Excellent! (2,200 reviews)
"H"
Reviewed on Jul 15, 2026
El Conquistador Resort
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
$424 nightly
The price is $462 total per night from Aug 9 to Aug 10
$462 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (3,534 reviews)
"Nuestra estadía fue excelente de principio a fin. Todo estuvo impecable: las habitaciones eran cómodas, limpias y bien cuidadas, el personal fue muy amable y atento en todo momento, y las instalaciones estaban en perfectas condiciones. El servicio superó nuestras expectativas y nos hicieron sentir ..."
Reviewed on Jul 15, 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
- Flights from Philadelphia (PHL) to San Juan (SJU)
- Flights from Los Angeles (LAX) to San Juan (SJU)
- Flights from Houston (IAH) to San Juan (SJU)
- Flights from Charlotte (CLT) to San Juan (SJU)
- Flights from Washington (DCA) to San Juan (SJU)
- Flights from Detroit (DTW) to San Juan (SJU)
- Flights from Dallas (DFW) to San Juan (SJU)
- Flights from Tampa (TPA) to San Juan (SJU)
- Flights from Raleigh (RDU) to San Juan (SJU)
- Flights from Hartford (BDL) to San Juan (SJU)
- Flights from New York (JFK) to San Juan (SJU)
- Flights from Baltimore (BWI) to San Juan (SJU)
- Flights to San Juan
- Flights from Orlando (MCO) to San Juan (SJU)
- Flights from Atlanta (ATL) to San Juan (SJU)
- Flights to Puerto Rico Island
- Flights from Miami (MIA) to San Juan (SJU)
- Flights to Puerto Rico
- Flights from New York (NYC) to San Juan (SJU)
- Flights from Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
- Flights from Boston (BOS) to San Juan (SJU)
- Flights from Chicago (ORD) to San Juan (SJU)
- Flights from Fort Lauderdale (FLL) to San Juan (SJU)
- Flights to Florida
- Casa del Libro
- San Juan Vacations
- Caracas Beach
- Condado Beach
- Museo de Casa Blanca
- Del Parque Theater
- Río Grande Vacations
- Felisa Rincon de Gautier Museum
- Aguas Claras Vacations
- Alcaldia
- Visit Luquillo
- Galeria Nacional
- Vieques Ferry Terminal
- Cataño Vacations
- La Chiva Beach
- Teatro Tapia
- San Jose Church
- La Coca Falls
- La Mina Falls
- El Capitolio
- Yokahu Tower
- Pablo Casals Museum
- Tercer Milenio Park
- San Juan Ferry Dock
- Las Paylas
- Ceiba Ferry Terminal
- Museo del Mar
- Nuestra Senora de Lourdes Chapel
- Casa de Ramon Power y Giralt
- San Juan Antiguo Vacations
- Convento de Los Dominicos
- Naguabo Vacations
- Puerto Rico Convention Center
- Fajardo Vacations
- Ceiba Vacations
- Carabali Rainforest Park
- Institute of Puerto Rican Culture
- Third Millennium Park
- Bioluminescent Bay
- Parque Nacional Balneario Seven Seas
- Pier 3
- Museo de Arte e Historia de San Juan
- Mora
- Palomino Island
- Puerto Rico Vacations
- Flamenco Beach
- Laguna Grande
- Culebra Vacations
- Castillo San Felipe del Morro Lighthouse
- Visit San Juan
- All inclusive Vacation Packages Puerto Rico
- El Yunque National Forest
- Visit Isla Verde
- Splash Tattoo
- Luquillo Beach
- Museum of our African Roots
- Balneario Seven Seas
- Capilla del Cristo
- Sheraton Casino
- Mercado Agricola Natural
- Arte & Mascaras
- Escambron Beach
- Canvas Art Gallery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
