Book Holiday Homes in Simpson Bay

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Featured Holiday Homes in Simpson Bay

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Simpson Bay
When you stay at this vacation home in Simpson Bay, you'll be on the beach, within a 5-minute drive of Mullet Bay Beach and Maho Beach.
Opens in a new windowAmazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
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
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
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Charming 3BR Villa w Private Pool in Pelican Key

Charming 3BR Villa w Private Pool in Pelican Key

Billy folly
The price is AU$1,026 per night from 28 Sept to 29 Sept
AU$1,026
28 Sept - 29 Sept
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
White Sands Retreat - Beachside at Beacon Hill

White Sands Retreat - Beachside at Beacon Hill

Beacon Hill
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
Villa Myles: Beachfront

Villa Myles: Beachfront

Simpson Bay
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 windowVilla Myles: Beachfront
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
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
Coco's Beach House with pool - Simpson Bay Beach

Coco's Beach House with pool - Simpson Bay Beach

Simpson Bay
When you stay at this vacation home in Simpson Bay, you'll be on the beach, within a 15-minute drive of Mullet Bay Beach and Grand Case Beach.
Opens in a new windowCoco's Beach House with pool - Simpson Bay Beach
Villa Ladida - Luxurious Villa with Magnificent view

Villa Ladida - Luxurious Villa with Magnificent view

Sint Maarten
With a stay at this villa 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
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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
53 Holiday Homes
Lowest Price
AU$173
Highest Price
AU$1,026
Popular accommodation
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool , 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, White Sands Retreat - Beachside at Beacon Hill, Villa Myles: Beachfront, Nice & Cosy 3BR Villa with private pool / Ocean View and beach access, Coco's Beach House with pool - Simpson Bay Beach, Villa Ladida - Luxurious Villa with Magnificent view

Top trending hotels in Simpson Bay

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
The price is AU$189 per night from 22 Oct to 23 Oct
AU$189
22 Oct - 23 Oct
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 30 Sept to 1 Oct
AU$173
30 Sept - 1 Oct
includes taxes & fees
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
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
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
Fully refundableReserve now, pay when you stay
The price is AU$212 per night from 28 Sept to 29 Sept
AU$212
28 Sept - 29 Sept
includes taxes & fees
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
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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.