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
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
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
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
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Caribbean Sea Studio next to The Morgan Resort

Caribbean Sea Studio next to The Morgan Resort

Maho, Sint Maarten
Stay at this vacation home in Simpson Bay. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Caribbean Sea Studio next to The Morgan Resort
Spacious, Beacon Hill House

Spacious, Beacon Hill House

Simpson Bay
Book a stay at this family-friendly vacation home in Simpson Bay. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Maho Beach and Mullet ...
Spacious, Beacon Hill House
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
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
Stay at this vacation home in Simpson Bay. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Maho Beach and Mullet Bay Beach are ...
La Madrague, cosy house with private pool few steps to the beach
Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club

Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club

2 out of 5
Simpson Bay
Stay at this vacation home in Simpson Bay. Enjoy free WiFi, tennis courts, and patios. Popular attractions Maho Beach and Orient Bay Beach are located ...
Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club
Peaceful Paradise

Peaceful Paradise

Koolbaai
Stay at this vacation home in Simpson Bay. Enjoy cable/satellite TV service and air conditioning. Popular attractions Maho Beach and Orient Bay Beach are located ...
Peaceful Paradise
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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
23 Holiday Homes
Lowest Price
NZ$266
Highest Price
NZ$585
Popular accommodation
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool , White Sands Retreat - Beachside at Beacon Hill, Nice & Cosy 3BR Villa with private pool / Ocean View and beach access, Caribbean Sea Studio next to The Morgan Resort, Spacious, Beacon Hill House, Villa Myles: Beachfront, La Madrague, cosy house with private pool few steps to the beach, Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club, Peaceful Paradise

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$585 per night from 24 Nov to 25 Nov
NZ$585
includes taxes & fees
24 Nov - 25 Nov
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$266 per night from 25 Nov to 26 Nov
NZ$266
includes taxes & fees
25 Nov - 26 Nov
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$335 per night from 24 Nov to 25 Nov
NZ$335
includes taxes & fees
24 Nov - 25 Nov
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$353 per night from 25 Nov to 26 Nov
NZ$353
includes taxes & fees
25 Nov - 26 Nov
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.