A beach with a large collection of seashells on the shore and a clear blue sky.

Five Cays Vacations from $1,372

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Five Cays Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 21 - Sep 25

    Windsong on the Reef + Flight

    Grace Bay
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,213 reviews)
    Roundtrip Boston (BOS) - Providenciales (PLS)
    BOS - PLS1 stop PLS - BOS1 stop
    $2,132
    $1,372
    per traveler
    found 1 day ago
    Windsong on the Reef
  • Oct 8 - Oct 12

    Long Bay Beach Club + Flight

    Long Bay Hills
    4 nights
    5.0 star property
    10/10 - Exceptional (4 reviews)
    "."
    Reviewed August 3, 2026
    Roundtrip Boston (BOS) - Providenciales (PLS)
    BOS - PLS1 stop PLS - BOS1 stop
    $6,634
    $3,553
    per traveler
    found 1 day ago
    Long Bay Beach Club
  • Sep 21 - Sep 25

    Dream Villas Provo + Flight

    Blue Hills
    4 nights
    3.5 star property
    9.2/10 - Wonderful (76 reviews)
    "This is a wonderful place for families to vacation and be like private. It was just a little while off from most stuff for us and we didn’t book a car. Taxis were expensive for where they were taking you it was 40 dollars to drive us 8 mins away and back to get food. Besides that it’s a very nice place on the less busy side of the island!"
    Reviewed August 2, 2026
    Roundtrip Boston (BOS) - Providenciales (PLS)
    BOS - PLS1 stop PLS - BOS1 stop
    $2,826
    $1,754
    per traveler
    found 1 day ago
    Dream Villas Provo
  • Oct 14 - Oct 19

    Point Grace + Flight

    Grace Bay
    5 nights
    4.5 star property
    9.6/10 - Exceptional (339 reviews)
    Roundtrip Boston (BOS) - Providenciales (PLS)
    BOS - PLS1 stop PLS - BOS1 stop
    $3,004
    $1,981
    per traveler
    found 1 day ago
    Point Grace
  • Oct 11 - Oct 17

    Ambergris Cay Private Island - All-Inclusive + Flight

    Big Ambergris Cay
    6 nights
    5.0 star property
    9.6/10 - Exceptional (24 reviews)
    "4 th stay . Waterfront bungalows are amazing if you want to swim and kayak to lunch ."
    Reviewed June 8, 2026
    Roundtrip Boston (BOS) - Providenciales (PLS)
    BOS - PLS1 stop PLS - BOS2 stops
    Save 100% on your flight
    $8,189
    $5,471
    per traveler
    found 1 day ago
    Ambergris Cay Private Island - All-Inclusive

What to do near Five Cays

Five Cays Hotel Deals

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.