Book Holiday Homes in Simpson Bay

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Featured Holiday Homes in Simpson Bay

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

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.
Opens in a new windowNew Listing, Exceptional 3 bed & bath with private pool in Pelican Cove
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

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.
Opens in a new windowAmazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
White Sands Retreat - Beachside at Beacon Hill

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.
Opens in a new windowWhite Sands Retreat - Beachside at Beacon Hill
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Dream Beachfront Home : Stunning sea views, private pool and walking distance

Dream Beachfront Home : Stunning sea views, private pool and walking distance

Koolbaai
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.
Opens in a new windowDream Beachfront Home : Stunning sea views, private pool and walking distance
Caribbean Sea Studio next to The Morgan Resort

Caribbean Sea Studio next to The Morgan Resort

Maho, Sint Maarten
The price is AU$704 per night from 29 Dec to 30 Dec
AU$704
29 Dec - 30 Dec
includes taxes & fees
With a stay at this vacation home in Simpson Bay, you'll be on the beach, steps from Maho Beach and a 2-minute drive from Mullet Bay Beach.
Opens in a new windowCaribbean Sea Studio next to The Morgan Resort
Charming 3BR Villa w Private Pool in Pelican Key

Charming 3BR Villa w Private Pool in Pelican Key

Billy folly Sint Maarten
The price is AU$1,359 per night from 13 Jan to 14 Jan
AU$1,359
13 Jan - 14 Jan 2026
includes taxes & fees
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.
Opens in a new windowCharming 3BR Villa w Private Pool in Pelican Key
Villa Ladida - Luxurious Villa with Magnificent view

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.
Opens in a new windowVilla Ladida - Luxurious Villa with Magnificent view
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access

Nice & Cosy 3BR Villa with private pool / Ocean View and beach access

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.
Opens in a new windowNice & Cosy 3BR Villa with private pool / Ocean View and beach access
La Madrague, cosy house with private pool few steps to the beach

La Madrague, cosy house with private pool few steps to the beach

Simpson Bay Sint Maarten
When you stay at this vacation home in Simpson Bay, you'll be by the sea, within a 5-minute drive of Maho Beach and Mullet Bay Beach.
Opens in a new windowLa Madrague, cosy house with private pool few steps to the beach
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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.

Simpson Bay Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Simpson Bay vacation homes are the perfect way for you to wing it.

Holiday houses in Simpson Bay let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Simpson Bay in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Simpson Bay adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Simpson Bay with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Simpson Bay vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Simpson Bay Holiday Homes essential information

Accommodation
33 Holiday Homes
Lowest Price
AU$563
Highest Price
AU$1,359
Popular accommodation
New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove, Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool , White Sands Retreat - Beachside at Beacon Hill, Dream Beachfront Home : Stunning sea views, private pool and walking distance , Caribbean Sea Studio next to The Morgan Resort, Charming 3BR Villa w Private Pool in Pelican Key, Villa Ladida - Luxurious Villa with Magnificent view, Nice & Cosy 3BR Villa with private pool / Ocean View and beach access, La Madrague, cosy house with private pool few steps to the beach

Top trending hotels in Simpson Bay

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
With a stay at The Morgan Resort Spa Village in Simpson Bay, you'll be steps from Maho Beach and a 2-minute drive from Mullet Bay Beach.
Opens in a new windowThe Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is AU$621 per night from 25 Jan to 26 Jan
AU$621
per night
25 Jan - 26 Jan
With a stay at Simpson Bay Resort, Marina & Spa in Simpson Bay, you'll be 3.5 mi (5.6 km) from Maho Beach and 3.9 mi (6.3 km) from Mullet Bay Beach.
Opens in a new windowSimpson 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
The price is AU$563 per night from 15 Jan to 16 Jan
AU$563
per night
15 Jan - 16 Jan
With a stay at Hilton Vacation Club Flamingo Beach St. Maarten in Simpson Bay (Pelican Key), you'll be within a 15-minute drive of Mullet Bay Beach and Grand ...
Opens in a new windowHilton Vacation Club Flamingo Beach St. Maarten
Save an average of 15% on thousands of hotels when you're signed in
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
The price is AU$865 per night from 6 Jan to 7 Jan
AU$865
per night
6 Jan - 7 Jan
Located in Simpson Bay, The Villas at Simpson Bay Resort is by the ocean, within a 10-minute drive of Great Bay Beach and Mullet Bay Beach.
Opens in a new windowThe Villas at Simpson Bay Resort
Don't see what you're looking for?
See all available properties in Simpson Bay
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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.

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^Subject to availability and chosen travel dates.