Book Holiday Homes in Simpson Bay

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Featured Holiday Homes in Simpson Bay

Large Pool/ 1 BR/1Bath  Apt. in Beautiful St. Martin in Simpson Bay!

Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay!

Simpson Bay
Stay at this vacation home in Simpson Bay. Enjoy a fitness center, air conditioning, and a hot tub. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay!
White Sands Retreat - Beachside at Beacon Hill

White Sands Retreat - Beachside at Beacon Hill

Beacon Hill
Book a stay at this beach vacation home in Simpson Bay. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Maho Beach and Mullet Bay Beach are ...
White Sands Retreat - Beachside at Beacon Hill
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Simpson Bay
Book a stay at this beach vacation home in Simpson Bay. Enjoy private pools, a beach locale, and concierge services. Popular attractions Maho Beach and Mullet ...
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
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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
Book a stay at this beach vacation home in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach ...
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access
Caribbean Sea Studio next to The Morgan Resort

Caribbean Sea Studio next to The Morgan Resort

Maho, Sint Maarten
Book a stay at this beach vacation home in Simpson Bay. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Maho Beach and Mullet Bay ...
Caribbean Sea Studio next to The Morgan Resort
Ruby Room  · CocoVaa Boutique Hotel - Ruby Suite

Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

Simpson Bay
Stay at this vacation home in Simpson Bay. Enjoy balconies and air conditioning. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite
Coco's Beach House with pool - Simpson Bay Beach

Coco's Beach House with pool - Simpson Bay Beach

Simpson Bay
Book a stay at this family-friendly vacation home in Simpson Bay. Enjoy a beach locale, a fitness center, and a garden. Popular attractions Maho Beach and Orient ...
Coco's Beach House with pool - Simpson Bay Beach
Villa Myles: Beachfront

Villa Myles: Beachfront

Simpson Bay
Book a stay at this beach vacation home in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach ...
Villa Myles: Beachfront
Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite

Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite

Simpson Bay
Stay at this vacation home in Simpson Bay. Enjoy balconies and air conditioning. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite
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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
27 Holiday Homes
Lowest Price
NZ$310
Highest Price
NZ$779
Popular accommodation
Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay!, White Sands Retreat - Beachside at Beacon Hill, Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool , Nice & Cosy 3BR Villa with private pool / Ocean View and beach access, Caribbean Sea Studio next to The Morgan Resort, Ruby Room · CocoVaa Boutique Hotel - Ruby Suite, Coco's Beach House with pool - Simpson Bay Beach, Villa Myles: Beachfront, Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite

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
The price is NZ$779 per night from 3 Apr to 4 Apr
NZ$779
includes taxes & fees
3 Apr - 4 Apr
Stay at this 4-star spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
The Morgan Resort Spa Village
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 NZ$310 per night from 29 Apr to 30 Apr
NZ$310
includes taxes & fees
29 Apr - 30 Apr
Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Simpson Bay Resort, Marina & Spa
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 NZ$419 per night from 29 Apr to 30 Apr
NZ$419
includes taxes & fees
29 Apr - 30 Apr
Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
The Villas at Simpson Bay Resort
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Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

3.5 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is NZ$350 per night from 2 May to 3 May
NZ$350
includes taxes & fees
2 May - 3 May
Stay at this 3.5-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
Hilton Vacation Club Flamingo Beach St. Maarten
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.