Roosevelt Roads Vacation Packages for 2026
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Roosevelt Roads Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Coral by the Sea Hotel
Isla Verde
$746
per person
Dec 23 - Dec 27
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
Stay at this hotel in Carolina. Enjoy free WiFi, 2 restaurants, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.
Convient location professional staff
Reviewed on Oct 20, 2026
Picuas Village
Zarzal
$1,247
per person
Dec 24 - Dec 30
found 1 hour ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
Book a stay at this beach villa in Río Grande. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Luquillo Beach and Wyndham Rio Mar Golf Course are located nearby.
Hyatt Regency Grand Reserve Puerto Rico
Zarzal
$1,830
per person
Dec 23 - Dec 27
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
Book a stay at this spa resort in Río Grande. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Luquillo Beach and Wyndham Rio Mar Golf Course are located nearby.
I was disappointed with my overall experience. Cleanliness could have been much better, and despite having 3 guests in the room, we constantly had to call for additional wash towels because there were never enough provided. The room also did not have a microwave, which was very inconvenient since we had food that needed reheating and ended up having to throw it away.
I also paid $95 for birthday decorations that, unfortunately, did not feel worth the price for what was provided. For the amount spent on the stay and extras, I expected a much better experience and more value for my money. I could have put that money toward a different resort with more amenities, potentially even an all-inclusive option.
I hope management takes this feedback seriously and considers offering a credit or discount toward a future stay to help make up for the disappointing experience. I would appreciate the opportunity to give the property another chance if these concerns could be addressed.
Reviewed on Oct 21, 2026
Ola Boutique Hotel
Condado
$912
per person
Dec 23 - Dec 27
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.
Trópica Beach Hotel
Santurce
$951
per person
Dec 23 - Dec 27
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, valet parking (surcharge), and a 24-hour business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.
Las Casitas Village at El Conquistador
Cabezas
$2,025
per person
Dec 23 - Dec 27
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
Book a stay at this luxury hotel in Fajardo. Enjoy free WiFi, 2 outdoor pools, and 10 restaurants. Popular attractions El Conquistador Golf Course and Las Croabas Bay are located nearby.
I paid for ocean view,but I didn't get it
Reviewed on Oct 21, 2026
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See all available trips from Columbus to Roosevelt Roads
View all tripsRoosevelt Roads Vacation Packages
Looking to save some money and some time on your next vacation to Roosevelt Roads? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Roosevelt Roads incredible. Our Travel Center is a one-stop shop where you can put together the best Roosevelt Roads vacation package for you and your family. We have an amazing list of accommodations and flight, and Roosevelt Roads activities to choose from.
Roosevelt Roads Hotel Deals
Our listings include accommodations that are close to all the Roosevelt Roads points of interest, and some that are just outside the city center for a quieter retreat.
From Roosevelt Roads hotels with pools and on-site restaurants, to boutique accommodations that add all the extra touches, you'll find a hotel here that will make your trip amazing. With AARP Travel Center's Roosevelt Roads hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Roosevelt Roads
You'll discover that Roosevelt Roads usually has something to see and do. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Book Together and Save
With so much happening in Roosevelt Roads, you'll be wanting to focus on your outings, not spending time to finding the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to quickly reserve everything you wish for, and save some cash at the same time. You can coordinate your whole trip, including things to do in Roosevelt Roads from just one place. The hardest packing you'll have to do is for your suitcase. Book today and save!
Top Hotel Deals
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Book a stay at this spa resort in Río Grande. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
El Conquistador Resort
1000 Conquistador Avenue Fajardo
Book a stay at this beach hotel in Fajardo. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Book a stay at this luxury resort in Río Grande. Enjoy 5 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful staff ...
Las Casitas Village at El Conquistador
1000 Avenida El Conquistador Fajardo
Book a stay at this luxury hotel in Fajardo. Enjoy free WiFi, 2 outdoor pools, and 10 restaurants. Popular attractions El Conquistador Golf Course and Las Croabas ...
Four Seasons Resort and Residences Puerto Rico
State Road 187 Kilometer 4.2 Río Grande
Book a stay at this luxury resort in Río Grande. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Fairfield by Marriott Luquillo Beach
3KM 36.0 MATA DE PLATANO Luquillo
Book a stay at this beach hotel in Luquillo. Enjoy free breakfast, free WiFi, and a casino. Our guests praise the breakfast and the helpful staff in our reviews. ...
Sea Gate Hotel
Route 989 Km .04 Vieques
Book a stay at this family-friendly hotel in Vieques. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean ...
Park Royal Club Cala managed by Accor
50 Club Cala Drive Humacao
Book a stay at this golf hotel in Humacao. Enjoy 2 outdoor pools, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
Wyndham Palmas Beach and Golf Boutique Resort
170 Candelero Drive, Palmas del Mar Humacao
Book a stay at this beach resort in Humacao. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
Selva Boutique Hotel - Luquillo Oceanfront Retreat - Adults only
6 Cll 1 Luquillo Luquillo
Book a stay at this beach hotel in Luquillo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Anchors Hotel
PR 987 BO Fajardo Fajardo
Stay at this hotel in Fajardo. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions El Conquistador Golf Course and Parque Nacional Balneario ...
Mata e' Platano Guesthouse
carr 992 Luquillo Luquillo
Stay at this guesthouse in Luquillo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Luquillo Beach and El Yunque National Forest are ...
Blue Horizon Boutique Resort - Adults Only
Carretara 996 Km 4.3 Vieques
Book a stay at this beach hotel in Vieques. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions ...
Trade Winds Restaurant & Guesthouse
107 Calle Flamboyan Esperanza Vieques Puerto Rico
Stay at this guesthouse in Vieques. Enjoy free WiFi, free parking, and a gift shop. Popular attractions Bioluminescent Bay and Vieques Ferry Terminal are located ...
CALIZO VIP GUEST HOUSE
Carr 987 Km 4.75 Las Croabas Fajardo Fajardo
Stay at this guesthouse in Fajardo. Enjoy free WiFi, free parking, and private pools. Popular attractions El Conquistador Golf Course and Parque Nacional Balneario ...
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See all available properties in Roosevelt Roads
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Nov 4 - Thu, Nov 5
MIA
Miami Intl.
SJU
Luis Munoz Marin Intl.
$83
Roundtrip
found 2 days ago
Mon, Oct 26 - Fri, Nov 6
BDL
Bradley Intl.
SJU
Luis Munoz Marin Intl.
$97
Roundtrip
found 3 days ago
Mon, Nov 9 - Thu, Nov 12
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$207
Roundtrip
found 11 hours ago
Sat, Dec 5 - Wed, Dec 16
LGA
LaGuardia
SJU
Luis Munoz Marin Intl.
$279
Roundtrip
found 4 days ago
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