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

Ciqala Suites Hotel
Santurce
Price was NZ$1,672, price is now NZ$1,184 per person
NZ$1,184
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
7.8/10 Good! (1,003 reviews)
We stayed here for three nights and we had an amazing experience. We stayed in the Presidential Suite and our room was beautiful. The staff here were so kind and helpful, rooftop restaurant was amazing. The hotel offered a shuttle to the beach and made to order breakfast every day. We would definitely stay here again.
Reviewed on 4 Jan 2026


Ola Boutique Hotel
Condado
Save 100% on your flight
Price was NZ$2,059, price is now NZ$1,424 per person
NZ$1,424
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
Staff was awesome, room was clean. Breakfast was the same every day, omelette, sausage/hot dogs, yogurt, strong coffee, and juice. Outside of the building didn’t match photos on website or Expedia. There were no amenities, rooftop was closed, no spa, no hot tub. Great access to everything in San Juan. No restaurant on site, no laundry, not in a nature reserve it’s in the middle of San Juan. No sauna, no banquet hall, elevator was questionable. For the price it was a great stay, but if you need a hot tub or spa you’ll have to drive. Check in wasn’t on time, but we got a similar room after waiting a few hours. No golf course nearby!
We really enjoyed our stay water pressure and temperature was awesome!
Reviewed on 3 Jan 2026

The Condado Plaza Hotel
Condado
Save 100% on your flight
Price was NZ$2,389, price is now NZ$1,664 per person
NZ$1,664
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The building looks run down the main entrance had a odor 1 elevator was in working order walking to our room mold was visible on walls entering our room it also had a odor the view made up for it but the railing on the patio was not that sturdy. Going forward updated photos of these building need to be taking the staff was great the beach was quite small I will definitely come back but will be staying in isla verde they have a beautiful beach and food was overall excellent nothing is all inclusive and prices are reasonable at restaurants away from them hotels
Reviewed on 4 Jan 2026

Romeo Gay Hotel
San Juan Antiguo
Price was NZ$1,657, price is now NZ$1,191 per person
NZ$1,191
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
9/10 Wonderful! (121 reviews)
Parking was good, hotel and room was clean, front desk was really nice and the location was good.
Reviewed on 30 Dec 2025
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Price found within the past 48 hours. Click for updated prices.

Condado Vanderbilt Hotel
Condado
Price was NZ$2,875, price is now NZ$2,463 per person
NZ$2,463
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
9.2/10 Wonderful! (1,616 reviews)
Beautiful hotel, great staff, lives up to its reputation.
Reviewed on 29 Dec 2025

Fairmont El San Juan Hotel
Isla Verde
Price was NZ$3,212, price is now NZ$2,768 per person
NZ$2,768
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
8.4/10 Very Good! (2,051 reviews)
The staff, especially Luis at The Lobby Bar, were pleasant and attentive. The servers on the beach seemed attentive to some and not to others. The food was delicious and the pools and beach phenomenal.
Reviewed on 2 Jan 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Mameyes II
Price was NZ$3,290, price is now NZ$2,864 per person
NZ$2,864
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
8.6/10 Excellent! (2,206 reviews)
We booked ocean view room three months in advance
Reviewed on 4 Jan 2026
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See all available trips from Columbus to Roosevelt Roads
View all trips4 Night Romantic holidays in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

Ola Boutique Hotel
Condado
Save 100% on your flight
Price was NZ$2,059, price is now NZ$1,424 per person
NZ$1,424
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
Staff was awesome, room was clean. Breakfast was the same every day, omelette, sausage/hot dogs, yogurt, strong coffee, and juice. Outside of the building didn’t match photos on website or Expedia. There were no amenities, rooftop was closed, no spa, no hot tub. Great access to everything in San Juan. No restaurant on site, no laundry, not in a nature reserve it’s in the middle of San Juan. No sauna, no banquet hall, elevator was questionable. For the price it was a great stay, but if you need a hot tub or spa you’ll have to drive. Check in wasn’t on time, but we got a similar room after waiting a few hours. No golf course nearby!
We really enjoyed our stay water pressure and temperature was awesome!
Reviewed on 3 Jan 2026


The Condado Plaza Hotel
Condado
Save 100% on your flight
Price was NZ$2,389, price is now NZ$1,664 per person
NZ$1,664
per person
10 Mar - 14 Mar
found 14 hours ago
Return flight included
New York (JFK) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The building looks run down the main entrance had a odor 1 elevator was in working order walking to our room mold was visible on walls entering our room it also had a odor the view made up for it but the railing on the patio was not that sturdy. Going forward updated photos of these building need to be taking the staff was great the beach was quite small I will definitely come back but will be staying in isla verde they have a beautiful beach and food was overall excellent nothing is all inclusive and prices are reasonable at restaurants away from them hotels
Reviewed on 4 Jan 2026
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See all available trips from Columbus 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.
