Puerto Rico Island Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Luxury vacation packages in Puerto Rico Island
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Price was ￥385,981, price is now ￥353,870 per person
￥353,870
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
The room was spotless and the views were amazing. The staff was beyond friendly. We had the most fabulous time and will return!
Reviewed on Feb 4, 2026
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Price was ￥448,432, price is now ￥381,136 per person
￥381,136
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9/10 Wonderful! (645 reviews)
Room was nice but small with a curious layout. Whole facility was nice and staff were very courteous and efficient. Sister property next door has a nice restaurant
Reviewed on Jan 24, 2026
The Condado Plaza Hotel
Condado
Price was ￥399,421, price is now ￥356,276 per person
￥356,276
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The staff was wonderful. I love the beach and the pools both at the Condado plaza and the Hilton. However, the sink in the bath room was not clean and the coffee maker did not work. Did call to have it switched out but there was no resolve.
Reviewed on Feb 7, 2026
Don't see what you're looking for?
See all available trips from Osaka to Puerto Rico Island
View all trips5* Luxury vacations in Puerto Rico Island
Price found within the past 48 hours. Click for updated prices.
Dorado Beach, a Ritz-Carlton Reserve
Higuillar
Price was ￥1,008,866, price is now ￥1,008,866 per person
￥1,008,866
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9.6/10 Exceptional! (229 reviews)
Top tier very cleanly excellent room service. Wonderful Beach service a must stay keep on your bucket list absolutely amazing views and a wonderful experience.
Reviewed on Feb 5, 2026
Don't see what you're looking for?
See all available trips from Osaka to Puerto Rico Island
View all trips3 Night Luxury vacations in Puerto Rico Island
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Price was ￥296,990, price is now ￥275,522 per person
￥275,522
per person
Mar 11 - Mar 13
found 20 hours ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
The room was spotless and the views were amazing. The staff was beyond friendly. We had the most fabulous time and will return!
Reviewed on Feb 4, 2026
The Condado Plaza Hotel
Condado
Price was ￥310,905, price is now ￥283,012 per person
￥283,012
per person
Mar 11 - Mar 13
found 20 hours ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The staff was wonderful. I love the beach and the pools both at the Condado plaza and the Hilton. However, the sink in the bath room was not clean and the coffee maker did not work. Did call to have it switched out but there was no resolve.
Reviewed on Feb 7, 2026
Don't see what you're looking for?
See all available trips from Osaka to Puerto Rico Island
View all trips4 Night Luxury vacations in Puerto Rico Island
Price found within the past 48 hours. Click for updated prices.
The Condado Plaza Hotel
Condado
Price was ￥399,421, price is now ￥356,276 per person
￥356,276
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
8/10 Very Good! (1,814 reviews)
The staff was wonderful. I love the beach and the pools both at the Condado plaza and the Hilton. However, the sink in the bath room was not clean and the coffee maker did not work. Did call to have it switched out but there was no resolve.
Reviewed on Feb 7, 2026
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Price was ￥448,432, price is now ￥381,136 per person
￥381,136
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9/10 Wonderful! (645 reviews)
Room was nice but small with a curious layout. Whole facility was nice and staff were very courteous and efficient. Sister property next door has a nice restaurant
Reviewed on Jan 24, 2026
Don't see what you're looking for?
See all available trips from Osaka to Puerto Rico Island
View all tripsTop Luxury Puerto Rico Island Hotels
Condado Vanderbilt Hotel
1055 Ashford Avenue San Juan
Condado Vanderbilt Hotel is a San Juan luxury 5-star beach property where you can treat yourself to 24-hour room service, pillowtop beds, and more. Deluxe amenities ...
9.2/10 Wonderful! (1,688 reviews)
everything is great
Reviewed on Feb 2, 2026
Hotel El Convento
100 Cristo St San Juan
Hotel El Convento is a San Juan luxury 4.5-star boutique property where you can pamper yourself with massage services, designer toiletries, and more. The outdoor ...
9/10 Wonderful! (1,003 reviews)
Wonderful hotel!
Reviewed on Jan 28, 2026
The St. Regis Bahia Beach Resort, Puerto Rico
State Road 187 Kilometer 4.2 Río Grande
Four Seasons Resort and Residence Puerto Rico is a lush 5-star beach property where you can be treated to deep soaking bathtubs and a champagne service. The ...
10/10 Exceptional! (4 reviews)
The greatest
Reviewed on Nov 22, 2025
Lowest 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
