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 laundry facilities. Popular attractions Maho Beach and Mullet ...
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
Stay at this vacation home in Simpson Bay. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Maho Beach and Mullet Bay Beach are located ...
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
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 ...
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 NZ$1,151 per night from 4 Oct to 5 Oct
NZ$1,151
4 Oct - 5 Oct
includes taxes & fees
Stay at this vacation home in Simpson Bay. Enjoy free WiFi, private pools, and a water park. Popular attractions Maho Beach and Mullet Bay Beach are located ...
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
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 ...
Opens in a new windowWhite Sands Retreat - Beachside at Beacon Hill
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 ...
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
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 ...
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
Book a stay at this family-friendly vacation home in Simpson Bay. Enjoy a beach locale, a fitness center, and a garden. Popular attractions Orient Bay 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
Stay at this villa in Simpson Bay. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Maho Beach and Mullet Bay 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
NZ$196
Highest Price
NZ$1,151
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 NZ$214 per night from 22 Oct to 23 Oct
NZ$214
22 Oct - 23 Oct
includes taxes & fees
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 ...
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 NZ$196 per night from 30 Sept to 1 Oct
NZ$196
30 Sept - 1 Oct
includes taxes & fees
Stay at this 4-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 reviews. ...
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
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. ...
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 NZ$241 per night from 29 Sept to 30 Sept
NZ$241
29 Sept - 30 Sept
includes taxes & fees
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 ...
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.

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