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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
16–21 Oct
,
4.97 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
5.0 out of 5 average rating, 246 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
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
3–8 Aug
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
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
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, 201 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
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
20–25 Jul
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5.0 out of 5 average rating, 26 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
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
20–25 Sept
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
5.0 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
27 Jul – 1 Aug
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
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
4.95 out of 5 average rating, 108 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Aug
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
5.0 out of 5 average rating, 43 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
4.9 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 3 bathrooms
2–7 Aug
Superhost
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Flat in Cole Bay
Luxurious Sunset Lagoon View
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
4–9 Aug
Top guest favourite
Apartment in Lowlands
Maho 1 Bed Condo with ocean view & Free Wi-Fi
4.9 out of 5 average rating, 52 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept