Book Holiday Homes in Simpson Bay

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Featured Holiday Homes in Simpson Bay

White Sands Retreat - Beachside at Beacon Hill

White Sands Retreat - Beachside at Beacon Hill

Beacon Hill Sint Maarten
Stay at this beach holiday home in Simpson Bay. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowWhite Sands Retreat - Beachside at Beacon Hill
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 holiday home in Simpson Bay. Enjoy free Wi-Fi, 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
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
Stay at this holiday home in Simpson Bay. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowNew Listing, Exceptional 3 bed & bath with private pool in Pelican Cove
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Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Simpson Bay Sint Maarten
Stay at this beach holiday home in Simpson Bay. Enjoy private pools, a beach locale and laundry facilities. Popular attractions Maho Beach and Mullet Bay Beach ...
Opens in a new windowAmazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
C324 - Amazing view with balcony

C324 - Amazing view with balcony

Simpson Bay Sint Maarten
Stay at this holiday home in Simpson Bay. Enjoy balconies and air conditioning. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Opens in a new windowC324 - Amazing view with balcony
Villa Ladida - Luxurious Villa with Magnificent view

Villa Ladida - Luxurious Villa with Magnificent view

Sint Maarten Sint Maarten
Stay at this holiday home in Simpson Bay. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Maho Beach and Mullet Bay ...
Opens in a new windowVilla Ladida - Luxurious Villa with Magnificent view
D403 - Very nice apartment with terrace

D403 - Very nice apartment with terrace

Cole Bay Sint Maarten
Stay at this holiday home in Simpson Bay. Enjoy air conditioning. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Opens in a new windowD403 - Very nice apartment with terrace
D401 Beautiful apartment with a garden lagoon view

D401 Beautiful apartment with a garden lagoon view

Cole Bay Sint Maarten
Stay at this holiday home in Simpson Bay. Enjoy air conditioning. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Opens in a new windowD401 Beautiful apartment with a garden lagoon view
Tropical 4-bedroom house with AC in Beacon Hill area

Tropical 4-bedroom house with AC in Beacon Hill area

Simpson Bay Sint Maarten
Stay at this holiday home in Simpson Bay. Enjoy laundry facilities and air conditioning. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowTropical 4-bedroom house with AC in Beacon Hill area
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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
41 Holiday Homes
Lowest Price
NZ$273
Highest Price
NZ$624
Popular accommodation
White Sands Retreat - Beachside at Beacon Hill, Dream Beachfront Home : Stunning sea views, private pool and walking distance , New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove, Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool , C324 - Amazing view with balcony, Villa Ladida - Luxurious Villa with Magnificent view, D403 - Very nice apartment with terrace, D401 Beautiful apartment with a garden lagoon view, Tropical 4-bedroom house with AC in Beacon Hill area

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$624 per night from 17 June to 18 June
NZ$624
17 June - 18 June
includes taxes & fees
Stay at this spa resort in Simpson Bay. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the pool and the restaurant in their reviews. ...
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
Fully refundableReserve now, pay when you stay
The price is NZ$503 per night from 15 June to 16 June
NZ$503
15 June - 16 June
includes taxes & fees
Stay at this beach resort in Simpson Bay. Enjoy free Wi-Fi, free parking and 6 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowSimpson 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$600 per night from 15 June to 16 June
NZ$600
15 June - 16 June
includes taxes & fees
Stay at this beach resort in Simpson Bay. Enjoy free Wi-Fi, free parking and 6 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowThe Villas at Simpson Bay Resort
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$273 per night from 25 May to 26 May
NZ$273
25 May - 26 May
includes taxes & fees
Stay at this beach resort in Simpson Bay. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowHilton 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.