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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay, Sint Maarten
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
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.89 out of 5 average rating, 66 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
19–24 Aug
4.97 out of 5 average rating, 79 reviews
Apartment in Philipsburg, Sint Maarten
Flamingo Beach by Hilton Grand Vacations- studio
1 king bed, 1 bathroom
6–11 Sept
Guest favourite
Villa in Simpson Bay, Sint Maarten
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
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 193 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
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
Guest favourite
Villa in Simpson Bay, Sint Maarten
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
Apartment in Cole Bay, Sint Maarten
PARADISE ONE TO LAS BRISAS
2 bedrooms, 2 beds, 2 bathrooms
1–6 Jul
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
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
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 bathrooms
11–16 Jul
New place to stay
Guest favourite
Villa in Simpson Bay, Sint Maarten
Villa Myles: Beachfront
3 bedrooms, 3 king beds, 3.5 bathrooms
6–11 Jul
4.79 out of 5 average rating, 19 reviews
Flat in Simpson Bay, Sint Maarten
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Jul
Guest favourite
Flat in Simpson Bay, Sint Maarten
OASIS Penthouse with private garden and Generator
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Jul
4.92 out of 5 average rating, 51 reviews
Top guest favourite
Home in Simpson Bay, Sint Maarten
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
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Pineapple Suite
2 bedrooms, 2 queen beds, 1 bathroom
28 Jul – 2 Aug
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Home in Lowlands, Sint Maarten
Brand NEW - Waterfront Villa - Pool
4 bedrooms, 4 double beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 244 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Caribbean Breeze in Paradise, SXM
2 bedrooms, 2 king beds, 2.5 bathrooms
2–7 Jul
5.0 out of 5 average rating, 40 reviews