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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
19–24 Jul
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4.95 out of 5 average rating, 108 reviews
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
12–17 Jul
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
4.85 out of 5 average rating, 200 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 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
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
5.0 out of 5 average rating, 64 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
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
1–6 Sept
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 3 bathrooms
9–14 Aug
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
7–12 Jul
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
4.89 out of 5 average rating, 132 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Flat in Lowlands
Luxury Studio| Walk to Maho Beach, Casino, Dinning
New place to stay, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
4.9 out of 5 average rating, 50 reviews, 3 bedrooms, 3 beds, 3 bathrooms
2–7 Aug
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
Flat in Simpson Bay
Lilly's Beach
4.95 out of 5 average rating, 236 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Aug
Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
21–26 Aug
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
4.95 out of 5 average rating, 110 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
4.97 out of 5 average rating, 79 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
4.96 out of 5 average rating, 103 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Aug
Top guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
4.98 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
27 Jul – 1 Aug