Simpson Bay Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Simpson Bay

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Simpson Bay Sint Maarten

When you stay at this vacation home in Simpson Bay, you'll be on the beach, within a 5-minute drive of Maho Beach and Mullet Bay Beach.

Pool

Kitchen

New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove

Pelican Key

With a stay at this vacation home in Simpson Bay (Pelican Key), you'll be within a 15-minute drive of Mullet Bay Beach and Grand Case Beach.

Pool

Kitchen

White Sands Retreat - Beachside at Beacon Hill

Beacon Hill Sint Maarten

When you stay at this vacation home in Simpson Bay, you'll be on the beach, within a 5-minute drive of Maho Beach and Mullet Bay Beach.

Kitchen

Washer

C324 - Amazing view with balcony

Simpson Bay Sint Maarten

With a stay at this vacation home in Simpson Bay, you'll be within a 15-minute drive of Maho Beach and Mullet Bay Beach.

Kitchen

Washer

Tropical 4-bedroom house with AC in Beacon Hill area

Simpson Bay Sint Maarten

With a stay at this vacation home in Simpson Bay, you'll be within a 5-minute drive of Maho Beach and Mullet Bay Beach.

Washer

Dryer

D432 Very beautiful apartment with a balcony

Cole Bay Sint Maarten

Located in Simpson Bay, this vacation home is within a 15-minute drive of Maho Beach and Mullet Bay Beach.

Villa Ladida - Luxurious Villa with Magnificent view

Sint Maarten Sint Maarten

With a stay at this vacation home in Simpson Bay (Pelican Key), you'll be within a 15-minute drive of Mullet Bay Beach and Grand Case Beach.

D403 - Very nice apartment with terrace

Cole Bay Sint Maarten

Located in Simpson Bay, this vacation home is within a 15-minute drive of Maho Beach and Mullet Bay Beach.

Pelican Pearl Villa - GENERATOR

Sint Maarten Sint Maarten

With a stay at this vacation home in Simpson Bay (Pelican Key), you'll be within a 15-minute drive of Mullet Bay Beach and Grand Case Beach.

D401 Beautiful apartment with a garden lagoon view

Cole Bay Sint Maarten

With a stay at this vacation home in Simpson Bay, you'll be within a 15-minute drive of Maho Beach and Mullet Bay Beach.

Planes & Paradise - Nirvana @ The Drake - Steps to the Beach

Simpson Bay

When you stay at this vacation home in Simpson Bay, you'll be near the beach, within a 5-minute drive of Maho Beach and Mullet Bay Beach.

The Luxe @ The Drake Residences - Private Beach Access + Runway Views

Simpson Bay

With a stay at this vacation home in Simpson Bay, you'll be within a 5-minute drive of Maho Beach and Mullet Bay Beach.

Don't see what you're looking for?

See all available properties in Simpson Bay

View all properties

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.