
Roosevelt Roads Beach Holidays
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Top flight + Beach hotel deals in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

Romeo Gay Hotel
San Juan Antiguo
Save 100% on your flight
Price was ₹95,994, price is now ₹60,864 per person
₹60,864
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
9/10 Wonderful! (121 reviews)
Super convenient location, bar across the street, convenience store and liquor across the street
The bar “5” across the street has pool table and Jenna games, super cool.
All entrances with gate security codes, common area to work and leave suitcase before and after check in/out
Very close to port and old San Juan.
Isla verde and condado 10 minute drive ( if that far)
We had an amazing time.
We travel with family
Reviewed on 6 Dec 2025

Ola Boutique Hotel
Condado
Save 100% on your flight
Price was ₹150,062, price is now ₹76,748 per person
₹76,748
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
PROS: Staff is amazing. Will do everything they can to accommodate you. Lobby, 1st floor is comfortable and inviting. Pool Table, Bar, Tables, Couches, Chairs. Nicely Decorated. Breakfast good for starting your day. could use a little more variety. Omelets, eggs, toast, lil sausages, ham, yogurt, coffee & juices, fresh fruit, cereal & waffle sticks. water available all day/night. Shower is next to bed, but wonderful and water pressure great! grocery store and food truck right out side!
CONS: Standard Room, furniture not efficiently placed. Bed WAY TOO SOFT! Flip that mattress!! no chair/couch to sit on, but chair was brought to room for us. No fridge, but gave us cooler for Ice. Very little storage. Toilet room ( no door ) has too much room that is wasted. Perfect for solo traveler. hard to crawl in bed no room as bed is up against wall. I have a cpap, and I had to put on bed leaning against wall as there was no place to put it. rearrange the room. move the hooks on wall to area near room connecting door. take fire ext. base out and put more hooks. NEED LIGHT above mirror.
Pictures are deceiving. Beach is not as close as stated by pictures. Great restaurants blocks away. be prepared to Uber. driving in PR is crazy.
Reviewed on 14 Dec 2025

Aire de O:live
Isla Verde
Save 100% on your flight
Price was ₹177,231, price is now ₹101,032 per person
₹101,032
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Staff was very friendly and helpful. Beach access was great. However the phone in the room did not work.
Reviewed on 11 Dec 2025

OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was ₹156,951, price is now ₹94,751 per person
₹94,751
per person
24 Feb - 28 Feb
found 1 hour ago
Return flight included
New York (NYC) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again.
Reviewed on 6 Dec 2025

The Condado Plaza Hotel
Condado
Save 100% on your flight
Price was ₹131,113, price is now ₹95,169 per person
₹95,169
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The hotel is and has always been an excellent hotel and location to stay at. Pool areas lower area check in , bar is very clean. I think some more work needs to be put in the hotel as far as aesthetics. Only one elevator was working for the entire stay and it was not enjoyable at all, That was the most frustrating experience . Some guests complained said it been so for over a week.
Reviewed on 14 Dec 2025
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Price found within the past 48 hours. Click for updated prices.

Condado Vanderbilt Hotel
Condado
Save 100% on your flight
Price was ₹169,363, price is now ₹123,673 per person
₹123,673
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
9.2/10 Wonderful! (1,616 reviews)
Room, staff, service, ambiance, location were perfect! I'll be back!
Reviewed on 14 Dec 2025

Fairmont El San Juan Hotel
Isla Verde
Save 100% on your flight
Price was ₹191,409, price is now ₹153,769 per person
₹153,769
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
8.4/10 Very Good! (2,051 reviews)
This is a wonderful property with incredible amenities. The service is not up to the level of the property. Some small changes would make a big difference such as teaching the staff to smile and be genuinely welcoming and to upgrade the level of English.
The steakhouse food is extraordinary however it has a discotheque mentality and it is hard to conduct business dinners with the high volume of the music.
Cleanliness is extraordinary.
A great place to stay but the staff needs some training and upgrading.
Reviewed on 14 Dec 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Mameyes II
Price was ₹160,245, price is now ₹135,033 per person
₹135,033
per person
2 Mar - 7 Mar
found 11 hours ago
Return direct flight included
Cleveland (CLE) to San Juan (SJU)
8.6/10 Excellent! (2,206 reviews)
While first getting acquainted with hotel was complicated at first because it’s so large, we soon got used to it. The rooms were beautiful, the food excellent, and the pool was fantastic. The kids loved the splash pad and slide. We also loved the beach which was clean and fun for the kids to play in the sand.
Reviewed on 14 Dec 2025
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See all available trips from Columbus to Roosevelt Roads
View all trips4 Night Beach holidays in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

The Condado Plaza Hotel
Condado
Save 100% on your flight
Price was ₹100,938, price is now ₹67,038 per person
₹67,038
per person
24 Feb - 28 Feb
found 1 hour ago
Return flight included
New York (NYC) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The hotel is and has always been an excellent hotel and location to stay at. Pool areas lower area check in , bar is very clean. I think some more work needs to be put in the hotel as far as aesthetics. Only one elevator was working for the entire stay and it was not enjoyable at all, That was the most frustrating experience . Some guests complained said it been so for over a week.
Reviewed on 14 Dec 2025

OLV Fifty Five - Adults Only
Condado
Save 100% on your flight
Price was ₹156,951, price is now ₹94,751 per person
₹94,751
per person
24 Feb - 28 Feb
found 1 hour ago
Return flight included
New York (NYC) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again.
Reviewed on 6 Dec 2025

Aire de O:live
Isla Verde
Save 100% on your flight
Price was ₹150,699, price is now ₹93,004 per person
₹93,004
per person
24 Feb - 28 Feb
found 1 hour ago
Return flight included
New York (NYC) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Staff was very friendly and helpful. Beach access was great. However the phone in the room did not work.
Reviewed on 11 Dec 2025
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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.
