Cay Bay Vacations from $988
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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.
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
Price was $1,423, price is now $988 per person
$988
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,008 reviews)
Suzanna and Hattie front desk ladies were fantastic! They helped me out so much! The driver was wonderful all the staff were so friendly! Love them. I will say if you’re not ready to walk up & down stairs, or don’t have a rental car, it was a little tough. Other than that no issues here friends and I enjoyed ourselves.
Reviewed on May 12, 2026
The Villas at Simpson Bay Resort
Pelican Key
Save 100% on your flight
Price was $2,301, price is now $1,194 per person
$1,194
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.2/10 Wonderful! (1,383 reviews)
Perfect place to stay close to everything!
Reviewed on May 15, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Save 100% on your flight
Price was $1,883, price is now $1,013 per person
$1,013
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
9/10 Wonderful! (1,695 reviews)
I could not have stayed at a better place! Simpson bay is centrally located to all the businesses. All the businesses will call the shuttle to the meeting point for you. It is quite large but by day two I could navigate by foot and the shuttle service is robust.
The staff were welcoming accommodating nothing felt like a money grab. I generally do not revisit resorts in search of different experiences. But I will be visiting again!
Reviewed on May 15, 2026
La Playa Orient Bay
Price was $1,638, price is now $1,146 per person
$1,146
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
9.4/10 Exceptional! (707 reviews)
The hotel was lovely and the staff were super accommodating and friendly. We enjoyed our vacation and the breakfast being included was really nice. The beach is gorgeous and the hotel is just a few steps away from the ocean. We ate lunch at the restaurant every day, the service was excellent and the staff were always super friendly. The food is great (I’d recommend the sushi or the chicken sandwich) Lots of beautiful dinner options right by the hotel. I cannot recommend La playa enough!
Reviewed on May 16, 2026
Cay Bay Hotel Deals
The Morgan Resort Spa Village
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
$370 nightly
The price is $385 total per night from Jun 7 to Jun 8
$385 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (2,143 reviews)
Experience at Morgan Resort was enjoyable from top to bottom!
Reviewed on May 15, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
1 Rhine Road Lowlands
$391 nightly
The price is $407 total per night from May 19 to May 20
$407 total
May 19 - May 20
Total with taxes and fees
8/10 Very Good! (2,934 reviews)
Excellent and polite staff. Impeccable restaurants and top notch buffet.
Reviewed on May 14, 2026
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
$252 nightly
The price is $264 total per night from Jun 15 to Jun 16
$264 total
Jun 15 - Jun 16
Total with taxes and fees
9/10 Wonderful! (1,728 reviews)
I could not have stayed at a better place! Simpson bay is centrally located to all the businesses. All the businesses will call the shuttle to the meeting point for you. It is quite large but by day two I could navigate by foot and the shuttle service is robust. The staff were welcoming accommodating ...
Reviewed on May 15, 2026
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.
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?
Seaside Nature Park
Explore the lovely green spaces of Seaside Nature Park and enjoy the boating in Cole Bay. Stroll along the seaside or discover the beautiful sunsets in this romantic area.
Things to do
Tango Sunset Cruise with Caribbean Dinner & Open Bar
$85
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.