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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 beds, 3 private bathrooms
9–14 Aug
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4.92 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Simpson Bay
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
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, 245 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed, 1 bathroom
10–15 Jul
4.85 out of 5 average rating, 200 reviews
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
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Villa in 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
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
4.89 out of 5 average rating, 132 reviews
Flat in Lowlands
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 Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
2–7 Aug
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
16–21 Oct
4.97 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 king bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 236 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 49 reviews
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
4.95 out of 5 average rating, 110 reviews
Guest favourite
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 103 reviews
Top guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
2 bedrooms, 2 king beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 55 reviews
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 15 reviews