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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
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4.97 out of 5 average rating, 106 reviews
Apartment in Philipsburg
Flamingo Beach by Hilton Grand Vacations- studio
1 king bed, 1 bathroom
12–17 Sept
Home in Koolbaai
Bahia - Villa 1
3 bedrooms, 3 beds, 2.5 bathrooms
21–28 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds, 3.5 bathrooms
4–9 Jul
4.97 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.9 out of 5 average rating, 67 reviews
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
9–14 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Simpson Bay
The Beach Condo
2 bedrooms, 2 king beds, 2.5 bathrooms
15–20 Aug
4.99 out of 5 average rating, 78 reviews
Flat in Lowlands
Luxury Studio| Walk to Maho Beach, Casino, Dinning
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
New place to stay
Guest favourite
Apartment in Cole Bay
PARADISE ONE TO LAS BRISAS
2 bedrooms, 2 beds, 2 bathrooms
25–30 Aug
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Cole Bay
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 14 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
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
Superhost
Apartment in Simpson Bay
Simpson Bay Beach - Modern 2 Bedroom -#1 Location
2 bedrooms, 2 king beds, 2.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Simpson Bay
Apartment on the beach
1 bedroom, 1 queen bed, 1 bathroom
23–28 Jul
4.88 out of 5 average rating, 243 reviews
Guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Jul
4.97 out of 5 average rating, 86 reviews
Guest favourite
Villa in Cole Bay
Amazing VIEWS! Private Pool *Blue Opal
5 bedrooms, 5 beds, 4 bathrooms
6–11 Jul
4.9 out of 5 average rating, 41 reviews
Top guest favourite
Home in Simpson Bay
Villa Blue View .. stunning views of endless sea!
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 91 reviews