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Search results; Over 1,000 homes in Simpson Bay

Superhost
Apartment in Simpson Bay
Oceanfront w Pool | Maho Beach area
1 bedroom, 2 beds, 1.5 private bathrooms
23–28 Aug
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4.8 out of 5 average rating, 188 reviews
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds
5–10 Aug
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed
1–6 Aug
5.0 out of 5 average rating, 247 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
1 queen bed
30 Aug – 4 Sept
4.89 out of 5 average rating, 18 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed
11–16 Aug
4.87 out of 5 average rating, 262 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds
9–14 Aug
4.92 out of 5 average rating, 25 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
2–7 Aug
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds
16–21 Oct
4.96 out of 5 average rating, 107 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds
5–10 Oct
5.0 out of 5 average rating, 76 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds
17–22 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Cole Bay
Luxurious Sunset Lagoon View
2 bedrooms, 2 beds
4–9 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds
16–21 Jul
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed
28 Jul – 2 Aug
4.85 out of 5 average rating, 202 reviews
Flat in Simpson Bay
Condo Josephine Maho Beacon Hill
2 bedrooms, 2 king beds
30 Jul – 4 Aug
4.79 out of 5 average rating, 14 reviews
Guest favourite
Hotel in Upper Prince's Quarter
Panorama SXM - 1 BR - Luxury Apartment
1 bedroom, 1 king bed
30 Jul – 4 Aug
5.0 out of 5 average rating, 5 reviews
Flat in Simpson Bay
Paradise by the Sea
2 bedrooms, 2 beds
21–26 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 queen bed
4–9 Aug
4.95 out of 5 average rating, 108 reviews