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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
Apartment in Philipsburg, Sint Maarten
Flamingo Beach by Hilton Grand Vacations- studio
1 king bed
12–17 Sept
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds
5–10 Jul
4.97 out of 5 average rating, 32 reviews
Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds
17–22 Jul
5.0 out of 5 average rating, 25 reviews
Home in Koolbaai, Sint Maarten
Bahia - Villa 1
3 bedrooms, 3 beds
21–28 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds
22–27 Aug
4.9 out of 5 average rating, 67 reviews
Flat in Simpson Bay, Sint Maarten
Luxury Beachfront Condo
2 bedrooms, 2 beds
12–17 Jul
Guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach
1 bedroom, 1 queen bed
23–28 Jul
4.88 out of 5 average rating, 243 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds
9–14 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds
21–26 Aug
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Beach Condo
2 bedrooms, 2 king beds
15–20 Aug
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
2 bedrooms, 2 king beds
23–28 Aug
4.98 out of 5 average rating, 50 reviews
Guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds
7–12 Jul
4.97 out of 5 average rating, 86 reviews
Top guest favourite
Home in Simpson Bay, Sint Maarten
Villa Blue View .. stunning views of endless sea!
4 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
11–16 Jul
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
1–6 Sept
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
SkyPort Condo
2 bedrooms, 2 beds
23–28 Jul
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds
30 Aug – 4 Sept
4.99 out of 5 average rating, 194 reviews
Top guest favourite
Flat in Cole Bay, Sint Maarten
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds
19–24 Aug
5.0 out of 5 average rating, 14 reviews