A coastal cliff with a lighthouse, clear blue sea, and rocky terrain.

Puerto Rico Island Luxury Vacations

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Top Luxury vacation packages in Puerto Rico Island

Price found within the past 48 hours. Click for updated prices.
  • Jan 11 - Jan 16

    OLV Fifty Five - Adults Only + Flight

    Condado
    5 nights
    4.5 star property
    8.8/10 - Excellent (827 reviews)
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 2 stops
    $1,751
    $1,287
    per traveler
    found 1 day ago
    OLV Fifty Five - Adults Only
  • Feb 5 - Feb 8

    Fairmont El San Juan Hotel + Flight

    Isla Verde
    3 nights
    5.0 star property
    8.6/10 - Excellent (2,237 reviews)
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 3 stops
    $1,750
    $1,315
    per traveler
    found 2 days ago
    Fairmont El San Juan Hotel
  • Jan 11 - Jan 16

    Condado Vanderbilt Hotel + Flight

    Condado
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,869 reviews)
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 2 stops
    $1,982
    $1,514
    per traveler
    found 1 day ago
    Condado Vanderbilt Hotel
  • Jan 10 - Jan 14

    Residences at Dorado Beach, a Ritz-Carlton Reserve + Flight

    Higuillar
    4 nights
    5.0 star property
    10/10 - Exceptional (2 reviews)
    "Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans. "
    Reviewed September 1, 2025
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 1 stop
    $18,139
    $14,134
    per traveler
    found 1 day ago
    Residences at Dorado Beach, a Ritz-Carlton Reserve
  • Jan 5 - Jan 10

    Royal Isabela + Flight

    Isabela
    5 nights
    4.5 star property
    9.6/10 - Exceptional (201 reviews)
    "Excelente servicio y la villa espectacular"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 1 stop
    $2,770
    $2,232
    per traveler
    found 22 hours ago
    Royal Isabela

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Top Luxury Puerto Rico Island Hotels

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.

All you need to know about luxury vacations in Puerto Rico Island

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 $1,287. 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.