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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest suite in Simpson Bay, Sint Maarten
Fig Paradis Penthouse
1 bedroom, 1 bed, 1 private bathroom
20–25 Jul
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4.97 out of 5 average rating, 79 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
21–26 Sept
4.99 out of 5 average rating, 328 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul
5.0 out of 5 average rating, 20 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 76 reviews
Flat in Lowlands, Sint Maarten
Luxury Studio| Walk to Maho Beach, Casino, Dinning
1 bedroom, 1 queen bed, 1 bathroom
28 Jul – 2 Aug
New place to stay
Guest favourite
Flat in Cole Bay, Sint Maarten
Luxurious Sunset Lagoon View
2 bedrooms, 2 beds, 2.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Blue Palm Estate Townhouse w/ Ocean View
2 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
4.95 out of 5 average rating, 21 reviews
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 bathrooms
11–16 Jul
New place to stay
Guest favourite
Villa in Indigo bay, Sint Maarten, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 64 reviews
Guest favourite
Flat in Grand-Case, St Martin
NEW: Unmatched Oceanfront Living in Grand Case
2 bedrooms, 2 beds, 2 bathrooms
26–31 Aug
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach 2
1 bedroom, 1 queen bed, 1 bathroom
10–15 Jul
4.85 out of 5 average rating, 200 reviews
Luxe
Home in Lowlands, Sint Maarten
Brand NEW - Waterfront Villa - Pool
4 bedrooms, 4 double beds, 4 bathrooms
6–11 Jul
5.0 out of 5 average rating, 24 reviews
Flat in Simpson Bay, Sint Maarten
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds, 3.5 bathrooms
8–13 Jul
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 64 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
OASIS Penthouse with private garden and Generator
2 bedrooms, 2 king beds, 2.5 bathrooms
13–18 Jul
4.92 out of 5 average rating, 52 reviews
Superhost
Flat in Cole Bay, Sint Maarten
Sunny Marina Residence
3 bedrooms, 4 beds, 3 bathrooms
19–24 Jul
4.83 out of 5 average rating, 24 reviews