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

The Condado Plaza Hotel
Condado
Price was ¥126,312, price is now ¥104,105 per person
¥104,105
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
8/10 Very Good! (2,526 reviews)
The place was nice the ppl were great. My room was beautiful
Reviewed on Jul 16, 2026

Hotel Puerto Valdes
San Juan Antiguo
Price was ¥154,310, price is now ¥106,968 per person
¥106,968
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) 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

OLV Fifty Five - Adults Only
Condado
Price was ¥224,819, price is now ¥172,186 per person
¥172,186
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
8.8/10 Excellent! (707 reviews)
I found intimate and very intimate stuff inside the shower,what made our night very uncomfortable ,knowing that we paid so much money for one night,
Reviewed on Jul 14, 2026

Hyatt Regency Grand Reserve Puerto Rico
Zarzal
Price was ¥160,816, price is now ¥129,429 per person
¥129,429
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
9/10 Wonderful! (3,023 reviews)
We stayed in the bungalows that were nice and spacious. We had a garden view which I enjoyed because it was very quiet at night for sleeping. We loved that the main pool was open 24/7. The staff was really nice and always tried their best to be helpful. The mini fridge in our room went bad on day 2 of being there and they brought us an older beat up mini fridge and just left in the middle of the room as replacement, I found this to be odd and distasteful. FYI the food at the resort was very overpriced and not that good unfortunately. Also before booking this hotel keep in mind they automatically add a ton of fees, taxes (taxes are HIGH) and tips when you order at any of the bars and restaurants (including room service).
Reviewed on Jul 16, 2026

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Price found within the past 48 hours. Click for updated prices.

Fairmont El San Juan Hotel
Isla Verde
Price was ¥154,622, price is now ¥127,690 per person
¥127,690
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
8.6/10 Excellent! (2,098 reviews)
Our stay at the Fairmont El San Juan was a great experience from start to finish. The property is beautiful, with a classic tropical feel that really makes you feel like you’re on vacation. The pools were clean and well maintained, the beach access was convenient, and the location in Isla Verde made it easy to explore the area while still feeling like a relaxing getaway.
The staff was friendly and welcoming throughout our stay, and housekeeping did an excellent job keeping our room clean. We also appreciated the variety of restaurants and bars on the property, which made it easy to find something for everyone.
One of the highlights was how lively the resort felt in the evenings, with great entertainment and a fun atmosphere without feeling overcrowded.
Overall, we had a wonderful family vacation and would definitely consider staying here again on a future trip to Puerto Rico. Thank you to the Fairmont El San Juan team for helping make our trip memorable!
Reviewed on Jul 16, 2026


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View all trips3 Night Luxury vacations in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

Hotel Puerto Valdes
San Juan Antiguo
Price was ¥154,310, price is now ¥106,968 per person
¥106,968
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) 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

OLV Fifty Five - Adults Only
Condado
Price was ¥224,819, price is now ¥172,186 per person
¥172,186
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
8.8/10 Excellent! (707 reviews)
I found intimate and very intimate stuff inside the shower,what made our night very uncomfortable ,knowing that we paid so much money for one night,
Reviewed on Jul 14, 2026

Hyatt Regency Grand Reserve Puerto Rico
Zarzal
Price was ¥160,816, price is now ¥129,429 per person
¥129,429
per person
Sep 4 - Sep 7
found 14 hours ago
Roundtrip flight included
New York (NYC) to San Juan (SJU)
9/10 Wonderful! (3,023 reviews)
We stayed in the bungalows that were nice and spacious. We had a garden view which I enjoyed because it was very quiet at night for sleeping. We loved that the main pool was open 24/7. The staff was really nice and always tried their best to be helpful. The mini fridge in our room went bad on day 2 of being there and they brought us an older beat up mini fridge and just left in the middle of the room as replacement, I found this to be odd and distasteful. FYI the food at the resort was very overpriced and not that good unfortunately. Also before booking this hotel keep in mind they automatically add a ton of fees, taxes (taxes are HIGH) and tips when you order at any of the bars and restaurants (including room service).
Reviewed on Jul 16, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
