
Roosevelt Roads Ski Vacations
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Top Ski vacation packages in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

Hotel Puerto Valdes
San Juan Antiguo
Price was ¥141,469, price is now ¥105,599 per person
¥105,599
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (500 reviews)
Very modern and clean. We stayed in the penthouse that is extremely spacious. Attentive staff and welcoming.
Reviewed on Nov 24, 2025

OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was ¥207,300, price is now ¥143,632 per person
¥143,632
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
The staff was amazing, best hotel stay I’ve had in awhile
Reviewed on Nov 30, 2025

Aire de O:live
Isla Verde
Save 100% on your flight
Price was ¥206,629, price is now ¥146,830 per person
¥146,830
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Overall this was a good romantic getaway. The beach is right there, and the service was great. Good food at the hotel restaurants. Not much around the area to walk to, but we had planned to Uber other places anyway. The hotel had some maintenance going on, so the pool area was noisy with construction. We also stayed on the 10th floor, and unfortunately heard a LOT of noise from the rooftop restaurant closing each night.
Reviewed on Dec 5, 2025

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Save 100% on your flight
Price was ¥186,940, price is now ¥138,300 per person
¥138,300
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (645 reviews)
Tatiana was a great host who helped us out tremendously.
Reviewed on Nov 30, 2025

Hyatt Regency Grand Reserve Puerto Rico
Zarzal
Price was ¥187,200, price is now ¥139,324 per person
¥139,324
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (2,764 reviews)
Pros: Room was nice, clean, and beautiful scenery and ambiance. Cons Pricey rest.in resort and wont accept food deliveries at the lobby, needed to travel on a golf cart to get my food at the security point. Beach is not good for swimming. Rent a car to get around.
Reviewed on Dec 5, 2025
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View all trips5* Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.


Fairmont El San Juan Villa Experience
Isla Verde
Save 100% on your flight
Price was ¥251,686, price is now ¥211,564 per person
¥211,564
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
7.6/10 Good! (128 reviews)
Bianca and Melanie at the front desk were both very helpful and accommodating.
Reviewed on Sep 28, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Mameyes II
Price was ¥210,646, price is now ¥180,397 per person
¥180,397
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
8.6/10 Excellent! (2,206 reviews)
Property under construction
Reviewed on Dec 5, 2025
Don't see what you're looking for?
See all available trips from New York to Roosevelt Roads
View all trips3 Night Ski vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Save 100% on your flight
Price was ¥186,940, price is now ¥138,300 per person
¥138,300
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (645 reviews)
Tatiana was a great host who helped us out tremendously.
Reviewed on Nov 30, 2025

OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was ¥207,300, price is now ¥143,632 per person
¥143,632
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
The staff was amazing, best hotel stay I’ve had in awhile
Reviewed on Nov 30, 2025

Aire de O:live
Isla Verde
Save 100% on your flight
Price was ¥206,629, price is now ¥146,830 per person
¥146,830
per person
Feb 24 - Feb 27
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Overall this was a good romantic getaway. The beach is right there, and the service was great. Good food at the hotel restaurants. Not much around the area to walk to, but we had planned to Uber other places anyway. The hotel had some maintenance going on, so the pool area was noisy with construction. We also stayed on the 10th floor, and unfortunately heard a LOT of noise from the rooftop restaurant closing each night.
Reviewed on Dec 5, 2025
Don't see what you're looking for?
See all available trips from New York to Roosevelt Roads
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
