Cay Bay Vacations from $752

Book a Hotel + Flight or Car together to unlock savings

Your Cay Bay Vacation

Immerse yourself in the best that Cay Bay offers with a Cay Bay vacation package. From its coastal beaches to everything else that makes it unique, this neighborhood will captivate you from start to finish. Your trip to Cay Bay has to include some sightseeing. Make time for popular attractions nearby such as Burgeaux Bay Beach. Whatever your travel goals or budget, booking your dream Cay Bay vacation is quick and easy with Expedia.

The Latest Cay Bay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,418, price is now $752 per person
$752
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,345 reviews)
They need some shuttles on property to move around.

Reviewed on Oct 1, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,800, price is now $894 per person
$894
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,241 reviews)
Central location, lots of options in walking distance. Clean resort, friendly staff. Budget friendly compared to other islands

Reviewed on Oct 3, 2025

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
Price was $1,816, price is now $942 per person
$942
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,116 reviews)
Great location. Big and comfortable rooms.

Reviewed on Oct 4, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,402, price is now $875 per person
$875
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (964 reviews)
Keep up your awesome work Team Princess Heghts! Your friends Anvar & Svetlana

Reviewed on Sep 25, 2025

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,243, price is now $782 per person
$782
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.4/10 Exceptional! (592 reviews)
It was okay, could be better

Reviewed on Sep 15, 2025

Cay Bay Hotel Deals

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
$221 nightly
The price is $231 total per night from Oct 6 to Oct 7
$231 total
Oct 6 - Oct 7
Total with taxes and fees
7.8/10 Good! (2,616 reviews)
"Cleanliness of resort Staff Food options"

Reviewed on Oct 2, 2025

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $126 total per night from Oct 19 to Oct 20
$126 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (1,366 reviews)
"They need some shuttles on property to move around."

Reviewed on Oct 1, 2025

Simpson Bay Resort, Marina & Spa
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $119 total per night from Oct 12 to Oct 13
$119 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,259 reviews)
"The check in staff were very friendly. However the pool bar female wo"

Reviewed on Sep 30, 2025

Hilton Vacation Club Flamingo Beach St. Maarten
See all 3,572 properties in Cay Bay
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 Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cay Bay

Indigo Beach

Why not spend a lazy afternoon at Indigo Beach during your trip to Cole Bay?

Indigo Beach

Seaside Nature Park

Explore the lovely green spaces of Seaside Nature Park and enjoy the boating in Cole Bay. Stroll along the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

Seaside Nature Park

Things to do

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

$100
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

$65
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Boomerang's Best of St. Martin/Maarten: Swim with Turtles

Boomerang's Best of St. Martin/Maarten: Swim with Turtles

$160
per adult
100% of travellers recommend
Boomerang's Best of St. Martin/Maarten: Swim with Turtles
See all activities in Cole Bay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.