Puerto Rico Island Luxury Vacations 2026

Top Luxury vacation packages in Puerto Rico Island

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

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

$440

per person

Oct 6 - Oct 8

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

9.2/10 Wonderful! (3,336 reviews)

I Would Highly Recommend This Hotel For Vacation, Activities, Events And All Around Stay. The Rooms Are Spacious, The Pool Area Is Amazing, The Beach Is Serene, The Foor Taste Great, The Staff Are Super Helpful And Friendly. I Would Definitely Be Back Again And Will Recommend It To My Family Members And Friends.

Reviewed on Sep 6, 2026

San Juan Marriott Resort and Stellaris Casino

Condado

Save 100% on your flight

$863

per person

Nov 6 - Nov 9

found 6 hours ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

9/10 Wonderful! (1,699 reviews)

Great place! Will visit again.

Reviewed on Sep 6, 2026

Residences at Dorado Beach, a Ritz-Carlton Reserve

Higuillar

Save 100% on your flight

$5,740

per person

Nov 6 - Nov 8

found 18 hours ago

Roundtrip flight included

Chicago (CHI) 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

Condado Vanderbilt Hotel

Condado

$1,040

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.4/10 Exceptional! (1,837 reviews)

Room advertised as queen bed had a full only. Room was a bit musty and ac was not great. All the onsite pools and areas were perfect

Reviewed on Sep 6, 2026

The Royal Sonesta San Juan

Isla Verde

Save 100% on your flight

$810

per person

Nov 6 - Nov 8

found 15 hours ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

9/10 Wonderful! (2,709 reviews)

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5* Luxury vacations in Puerto Rico Island

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

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Mameyes II

$960

per person

Nov 10 - Nov 13

found 6 hours ago

Roundtrip flight included

Baltimore (BWI) to San Juan (SJU)

8.6/10 Excellent! (2,295 reviews)

Residences at Dorado Beach, a Ritz-Carlton Reserve

Higuillar

Save 100% on your flight

$5,740

per person

Nov 6 - Nov 8

found 18 hours ago

Roundtrip flight included

Chicago (CHI) 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

Condado Vanderbilt Hotel

Condado

$1,040

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.4/10 Exceptional! (1,837 reviews)

Room advertised as queen bed had a full only. Room was a bit musty and ac was not great. All the onsite pools and areas were perfect

Reviewed on Sep 6, 2026

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3 Night Luxury vacations in Puerto Rico Island

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

Ciqala Suites Hotel

Santurce

$453

per person

Nov 6 - Nov 9

just found

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

8.2/10 Very Good! (1,013 reviews)

Reviewed on Sep 4, 2026

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

Save 100% on your flight

$729

per person

Nov 6 - Nov 9

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

9.2/10 Wonderful! (3,336 reviews)

Reviewed on Sep 6, 2026

Residences at Dorado Beach, a Ritz-Carlton Reserve

Higuillar

Save 100% on your flight

$8,304

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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

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4 Night Luxury vacations in Puerto Rico Island

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

S.J. Suites Hotel

Old San Juan

Save 100% on your flight

$351

per person

Nov 6 - Nov 10

found 4 hours ago

Roundtrip flight included

Atlanta (ATL) to San Juan (SJU)

7.8/10 Good! (486 reviews)

The hotel is a catfish the rooms are horrible and the walls are paper thin you can hear all the snoares and TVs on the floor you stay and the entire hotel smells like wet dog probably because they don’t change their A/C filters

Reviewed on Sep 6, 2026

Hyatt Regency Grand Reserve Puerto Rico

Zarzal

Save 100% on your flight

$1,429

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.2/10 Wonderful! (3,336 reviews)

Reviewed on Sep 6, 2026

La Terraza de San Juan

Old San Juan

$793

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip flight included

New York (JFK) to San Juan (SJU)

8.4/10 Very Good! (1,017 reviews)

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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 $351. 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! (1,849 reviews)

"Room advertised as queen bed had a full only. Room was a bit musty and ac was not great. All the onsite pools and areas were perfect"

Reviewed on Sep 6, 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 ...

See all 7,989 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.