Resorts in Simpson Bay

Sat, Nov 29
Mon, Dec 1
November 2025
25
December 2025

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14
In one month
Dec 26 - Dec 28
In two months
Jan 23 - Jan 25

Resorts in Simpson Bay

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key
CA $125
CA $169 total
includes taxes & fees
Dec 10 - Dec 11
Hilton Vacation Club Flamingo Beach St. Maarten

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $209
CA $251 total
includes taxes & fees
Dec 15 - Dec 16
Simpson Bay Resort, Marina & Spa

The Villas at Simpson Bay Resort

Simpson Bay
CA $225
CA $271 total
includes taxes & fees
Dec 1 - Dec 2
The Villas at Simpson Bay Resort

The Morgan Resort Spa Village

Simpson Bay
CA $275
CA $372 total
includes taxes & fees
Nov 26 - Nov 27
The Morgan Resort Spa Village

Port de Plaisance Resort, Trademark Collection by Wyndham

Cole Bay
CA $208
CA $218 total
includes taxes & fees
Nov 27 - Nov 28
Port de Plaisance Resort, Trademark Collection by Wyndham

Royal Islander Resort La Plage

Lowlands
Royal Islander Resort La Plage

Sapphire Beach Club Resort

Maho
CA $153
CA $183 total
includes taxes & fees
Nov 26 - Nov 27
Sapphire Beach Club Resort

Oyster Bay Beach Resort

Oyster Pond
CA $232
CA $278 total
includes taxes & fees
Dec 1 - Dec 2
Oyster Bay Beach Resort

Divi Little Bay Beach Resort

Philipsburg
Divi Little Bay Beach Resort
See more properties

The Black Friday Sale is now on

Get up to 50% off select hotels in our biggest sale of the year
Shop Black Friday deals

Top neighborhoods in Simpson Bay

Pelican Key

The Pelican Key neighborhood offers attractions such as Flamingo Beach and Lay Bay Beach.

Top landmarks in Simpson Bay

Kim Sha Beach
Kim Sha Beach

Kim Sha Beach

4/5(17 reviews)

If being by the water is a major draw, Kim Sha Beach is a spot you might want to check out, located 0.3 mi (0.5 km) from central Simpson Bay. If you want to continue walking by the waves, head to Flamingo Beach and Lay Bay Beach, both within a short walk.

See properties in Kim Sha Beach
Hollywood Casino
Hollywood Casino which includes a casino and interior views

Hollywood Casino

Why not roll the dice with a visit to Hollywood Casino during your visit to Simpson Bay? Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

See properties in Hollywood Casino
Simpson Bay Beach

Simpson Bay Beach

4/5(5 reviews)

When the beach is calling your name, you might want to head down to Simpson Bay Beach, located 1 mi (1.6 km) from central Simpson Bay. If you want to continue walking by the waves, head to Maho Beach located nearby.

See properties in Simpson Bay Beach
Flamingo Beach

Flamingo Beach

If want to top up your tan, you might want to head out to Flamingo Beach, located 0.5 mi (0.8 km) from central Simpson Bay. If you want to continue walking by the waves, head to Kim Sha Beach and Lay Bay Beach, both within a short walk.

See properties in Flamingo Beach
Lay Bay Beach

Lay Bay Beach

Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?

See properties in Lay Bay Beach
Dunes Casino

Dunes Casino

Why not roll the dice with a visit to Dunes Casino during your travels in Beacon Hill? Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

See properties in Dunes Casino

Learn more about Simpson Bay

Admired for its live music and entertainment, Simpson Bay features attractions such as Kim Sha Beach and Flamingo Beach. This beachside city has something for everyone including its casinos, restaurants, and sights like Simpson Bay Beach and Hollywood Casino.

See all hotels in Simpson Bay
Kim Sha Beach showing general coastal views and a coastal town

Find out more about Simpson Bay

Simpson Bay is a romantic destination known for its restaurants and bars. Hunt for sand dollars at Kim Sha Beach and Flamingo Beach. Popular sights in the surrounding area include Maho Beach and Orient Bay Beach.

Keep exploring