Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
22–27 Jun
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4.95 out of 5 average rating, 108 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Ultra Luxury Modern Condo / Beach Views
2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jun
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Koolbaai
Luxury Villa Turquoise Heaven in Pelican Key
3 bedrooms, 4 beds, 2.5 bathrooms
15–22 Dec
4.89 out of 5 average rating, 38 reviews
Top guest favourite
Flat in Cole Bay
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds, 1 bathroom
23–28 Jun
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jun
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 243 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
26 Jun – 1 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
16–21 Sept
4.99 out of 5 average rating, 324 reviews
Top guest favourite
Flat in Cupecoy
Stunning oceanfront condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
21–26 Jun
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
1 queen bed, 1 bathroom
8–13 Aug
4.93 out of 5 average rating, 14 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 53 reviews
Guest favourite
Flat in Cole Bay
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Villa in Indigo bay, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Nov
4.95 out of 5 average rating, 60 reviews
Guest favourite
Apartment in Simpson Bay
Five Star Luxury Beachfront Condo Private Hot Tub
2 bedrooms, 2 king beds, 2.5 bathrooms
19–24 Jun
4.94 out of 5 average rating, 87 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
21–26 Jun
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Place to stay in Simpson Bay
The Hideaway
1 queen bed, 1 bathroom
18–23 Jun
4.94 out of 5 average rating, 36 reviews
Guest favourite
Flat in Pelican
Luxurious Hidden Pearl - Private Pool
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 18 reviews
Guest favourite
Apartment in Simpson Bay
SeaViews 2Brm Ocean Front Condo SXM
2 bedrooms, 2 beds, 2 bathrooms
28 Jun – 3 Jul
4.88 out of 5 average rating, 26 reviews