Five Cays Vacation Packages 2026 from $1,745

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The Latest Five Cays vacation packages

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

Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,745

per person

May 21 - May 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (1,026 reviews)

We were very happy with every part of our stay at Windsong on the Reef! Everyone is so friendly and helpful. We loved the beach activities!

Reviewed on Mar 13, 2026

Dream Villas Provo

Save 100% on your flight

$2,163

per person

May 21 - May 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (58 reviews)

Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation!

Reviewed on Feb 26, 2026

Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,296

per person

May 21 - May 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (118 reviews)

-The free bikes need upgrading -Wish there was a place to hose off sand on your feet after coming from the beach -Rooftop restaurant had excellent food. We had prime rib and it was the best ! -Loved our room at the Beachfront at Windsong -Liked using phone number to get into room

Reviewed on Mar 13, 2026

The Park at Grace Bay

Grace Bay

Save 100% on your flight

$2,385

per person

May 21 - May 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

No reviews

Rock House

Save 100% on your flight

$4,361

per person

May 21 - May 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.6/10 Exceptional! (376 reviews)

Excellent staff - thoughtful, considerate. Beautiful, well-appointed accommodations.

Reviewed on Mar 9, 2026

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Five Cays Hotel Deals

Le Bleu Bed and Breakfast

30 Five Cays Rd Providenciales Caicos Islands

$219 nightly

$268 total

Apr 1 - Apr 2

Total with taxes and fees

7.2/10 Good! (118 reviews)

Amazing place.

Reviewed on Feb 28, 2026

Windsong on the Reef

Stubbs Rd Providenciales Providenciales

$548 nightly

$662 total

Mar 23 - Mar 24

Total with taxes and fees

9.2/10 Wonderful! (1,005 reviews)

We were very happy with every part of our stay at Windsong on the Reef! Everyone is so friendly and helpful. We loved the beach activities!

Reviewed on Mar 13, 2026

Ports of Call Resort

Grace Bay Road Providenciales

$408 nightly

$494 total

Apr 2 - Apr 3

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

Staff was great! Cortez at the bar was amazing. I would go back in a heartbeat.

Reviewed on Mar 11, 2026

See all 1,645 properties in Five Cays

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.