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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
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
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 76 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
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
Flat in Simpson Bay
The luxe 1 bedr apt with pool and Generator
1 bedroom, 1 king bed, 1 bathroom
22–27 Jun
4.95 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed, 1 bathroom
23–28 Jun
4.85 out of 5 average rating, 199 reviews
Guest favourite
Apartment in Lowlands
Maho studio overlooking airport, Free Wi-Fi!
1 bed, 1 bathroom
27 Jun – 2 Jul
4.84 out of 5 average rating, 95 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
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
25–30 Jun
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
4.88 out of 5 average rating, 127 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
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 king bed, 1 bathroom
17–22 Jul
4.95 out of 5 average rating, 233 reviews
Guest favourite
Serviced apartment in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
29 Jun – 4 Jul
4.92 out of 5 average rating, 72 reviews
Guest favourite
Flat in Cupecoy Beach
B-702 Stunning Ocean view corner unit
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 18 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
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 Cole Bay
Luxurious Sunset Lagoon View
2 bedrooms, 2 beds, 2.5 bathrooms
23–28 Jun
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 78 reviews