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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 bed, 1 bathroom
9–14 Jul
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4.95 out of 5 average rating, 236 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
5.0 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
Top guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
5.0 out of 5 average rating, 76 reviews, 2 beds, 1.5 bathrooms
31 Jul – 5 Aug
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
4.99 out of 5 average rating, 328 reviews, 3 bedrooms, 4 beds, 3 bathrooms
21–26 Sept
Guest favourite
Villa in Indigo bay, Sint Maarten
Ocean Dream Villa
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
Guest favourite
Townhouse in Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
4.96 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Oct
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4 bathrooms
18–23 Aug
Luxe
Home in Lowlands
Brand NEW - Waterfront Villa - Pool
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 4 bathrooms
6–11 Jul
Guest favourite
Villa in Indigo Bay
Villa Ocean - Indulge Yourself in Paradise
4.95 out of 5 average rating, 77 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Flat in Simpson Bay
Apartment in Simpson bay
New place to stay, 1 bedroom, 2 beds, 1 bathroom
10–15 Jul
Top guest favourite
Home in Koolbaai
Blue Palm Estate Townhouse w/ Ocean View
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
5.0 out of 5 average rating, 245 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
Guest favourite
Flat in Upper Prince's Quarter
Aman_Aria
4.97 out of 5 average rating, 36 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🀩😍
4.97 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
16–21 Oct
Top guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
4.96 out of 5 average rating, 52 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Cole Bay
Luxurious Sunset Lagoon View
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
24–29 Aug