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

Puerto Rico Island Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

Top Luxury vacation packages in Puerto Rico Island

Price found within the past 48 hours. Click for updated prices.
  • Dec 18 - Dec 21

    Fairmont El San Juan Hotel + Flight

    Isla Verde
    3 nights
    5.0 star property
    8.6/10 - Excellent (2,237 reviews)
    "The hotel was tired and need of upkeep. The grounds and beach were lovely though."
    Reviewed November 14, 2026
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • Nonstop
    $1,007
    $784
    per traveler
    found 1 day ago
    Fairmont El San Juan Hotel
  • Dec 31 - Jan 4

    Ola Boutique Hotel + Flight

    Condado
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,060 reviews)
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 1 stop
    $1,955
    $1,242
    per traveler
    found 1 day ago
    Ola Boutique Hotel
  • Dec 20 - Dec 25

    Las Casitas Village at El Conquistador + Flight

    Cabezas
    5 nights
    4.5 star property
    9.2/10 - Wonderful (320 reviews)
    "Everything was excellent!! Exceeded my expectations!!"
    Reviewed November 13, 2026
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • Nonstop
    $2,537
    $1,693
    per traveler
    found 1 day ago
    Las Casitas Village at El Conquistador
  • Dec 31 - Jan 4

    OLV Fifty Five - Adults Only + Flight

    Condado
    4 nights
    4.5 star property
    8.8/10 - Excellent (831 reviews)
    Roundtrip • Boston (BOS) - San Juan (SJU)
    BOS - SJU • Nonstop SJU - BOS • 1 stop
    $2,160
    $1,632
    per traveler
    found 1 day ago
    OLV Fifty Five - Adults Only
  • Feb 1 - Feb 6

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

    Higuillar
    5 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
    Save 100% on your flight
    $22,046
    $17,193
    per traveler
    found 15 hours ago
    Residences at Dorado Beach, a Ritz-Carlton Reserve

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What to do in Puerto Rico Island

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 $784. 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.