Puerto Rico Island Luxury Vacations 2026

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Top Luxury vacation packages in Puerto Rico Island

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

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Condado

$605

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip flight included

New York (NYC) to San Juan (SJU)

9/10 Wonderful! (680 reviews)

El Conquistador Resort

Cabezas

$645

per person

Oct 15 - Oct 17

found 1 hour ago

Roundtrip non-stop flight included

Minneapolis (MSP) to San Juan (SJU)

9/10 Wonderful! (3,538 reviews)

Residences at Dorado Beach, a Ritz-Carlton Reserve

Higuillar

Save 100% on your flight

$8,900

per person

Oct 15 - Oct 18

found 3 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

10/10 Exceptional! (2 reviews)

Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans.

Reviewed on Sep 1, 2025

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

$719

per person

Oct 15 - Oct 17

found 23 hours ago

Roundtrip flight included

Minneapolis (MSP) to San Juan (SJU)

9/10 Wonderful! (3,176 reviews)

This place was truly a DREAM! From the moment we arrived, everything felt so beautiful, peaceful, and perfect. I honestly couldn’t believe how incredible everything was. The entire experience felt almost unreal. This was, without a doubt, one of the most amazing vacations my family has ever had, and a huge part of that was staying here. The beauty, the atmosphere, the hospitality, and the overall experience exceeded every expectation I had. I genuinely did NOT want to leave! If you’re considering staying here, let me save you the time—you absolutely should. I would recommend this place to ANYBODY and EVERYBODY looking for the perfect vacation experience. Thank you for giving my family memories we’ll never forget. Until next time!

Reviewed on Aug 14, 2026

San Juan Marriott Resort and Stellaris Casino

Condado

$700

per person

Oct 15 - Oct 17

found 23 hours ago

Roundtrip flight included

Minneapolis (MSP) to San Juan (SJU)

9/10 Wonderful! (1,662 reviews)

AAAAA+ room

Reviewed on Aug 15, 2026

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5* Luxury vacations in Puerto Rico Island

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

Condado Vanderbilt Hotel

Condado

$585

per person

Sep 14 - Sep 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.4/10 Exceptional! (1,795 reviews)

Hotel room was not clean in the beginning very dusty and we got stuck with 666 so that was creepy but overall loved it (:

Reviewed on Aug 14, 2026

Residences at Dorado Beach, a Ritz-Carlton Reserve

Higuillar

Save 100% on your flight

$8,900

per person

Oct 15 - Oct 18

found 3 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

10/10 Exceptional! (2 reviews)

Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans.

Reviewed on Sep 1, 2025

Four Seasons Resort and Residences Puerto Rico

Herreras

$1,596

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to San Juan (SJU)

9.6/10 Exceptional! (28 reviews)

Outstanding customer service. All of the staff was amazing. Davette and Jose were amazing at the main restaurant. Shakiel was also amazing. All the staff was amazing.

Reviewed on Aug 11, 2026

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3 Night Luxury vacations in Puerto Rico Island

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

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

$587

per person

Sep 14 - Sep 17

found 1 hour ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9/10 Wonderful! (3,176 reviews)

Reviewed on Aug 14, 2026

San Juan Marriott Resort and Stellaris Casino

Condado

$751

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

9/10 Wonderful! (1,662 reviews)

AAAAA+ room

Reviewed on Aug 15, 2026

Four Seasons Resort and Residences Puerto Rico

Herreras

$1,103

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to San Juan (SJU)

9.6/10 Exceptional! (28 reviews)

Outstanding customer service. All of the staff was amazing. Davette and Jose were amazing at the main restaurant. Shakiel was also amazing. All the staff was amazing.

Reviewed on Aug 11, 2026

Don't see what you're looking for?

See all available trips from Columbus to Puerto Rico Island

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4 Night Luxury vacations in Puerto Rico Island

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

Hotel Rumbao, a Tribute Portfolio Hotel

Old San Juan

$484

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to San Juan (SJU)

9/10 Wonderful! (1,833 reviews)

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

Save 100% on your flight

$586

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to San Juan (SJU)

9/10 Wonderful! (3,176 reviews)

Reviewed on Aug 14, 2026

El Conquistador Resort

Cabezas

$636

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to San Juan (SJU)

9/10 Wonderful! (3,538 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Puerto Rico Island

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What can I expect from a luxury Puerto Rico Island vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Puerto Rico Island vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Puerto Rico Island?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Puerto Rico Island luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $484. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Puerto Rico Island?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Puerto Rico Island with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Puerto Rico Island?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Puerto Rico Island with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Puerto Rico Island with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Puerto Rico Island Hotels

Condado Vanderbilt Hotel

1055 Ashford Avenue San Juan

50 min drive from El Yunque National Forest

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 ...

9.4/10 Exceptional! (1,832 reviews)

"Hotel room was not clean in the beginning very dusty and we got stuck with 666 so that was creepy but overall loved it (:"

Reviewed on Aug 14, 2026

Hotel El Convento

100 Cristo St San Juan

56 min drive from El Yunque National Forest

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 ...

Four Seasons Resort and Residences Puerto Rico

State Road 187 Kilometer 4.2 Río Grande

20 min drive from El Yunque National Forest

Four Seasons Resort and Residences Puerto Rico is a lush 5-star beach property where you can be treated to deep soaking bathtubs and a champagne service. The ...

9.6/10 Exceptional! (31 reviews)

"Outstanding customer service. All of the staff was amazing. Davette and Jose were amazing at the main restaurant. Shakiel was also amazing. All the staff was amazing."

Reviewed on Aug 11, 2026

See all 7,962 properties in Puerto Rico Island

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.