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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
Studio, 2 beds, 1.5 private bathrooms
26 Nov – 1 Dec
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5.0 out of 5 average rating, 83 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Villa in Cole Bay, Sint Maarten
Pelican Key*Amazing VIEWS! Private Pool *
5 bedrooms, 5 beds, 4 bathrooms
7–12 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
24–29 Apr
4.96 out of 5 average rating, 109 reviews
Guest favourite
Villa in Koolbaai, Sint Maarten
Villa Livity 6 Bed Luxury Sea view boutique villa
6 bedrooms, 6 beds, 6.5 bathrooms
7–12 Sept
4.91 out of 5 average rating, 46 reviews
Superhost
Flat in Cupecoy, Sint Maarten
Ocean Paradise Condo - The Cliff
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
New place to stay
Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Villa in Simpson Bay, Sint Maarten
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds, 6 bathrooms
25–30 Oct
4.98 out of 5 average rating, 95 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool C2.1
4 bedrooms, 5 beds, 4 bathrooms
14–19 Sept
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
4.99 out of 5 average rating, 335 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Royal Palm Hilton SXM
2 bedrooms, 3 beds, 2 bathrooms
9–16 Sept
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Home in Cole Bay, Sint Maarten
Puerta Al Mar - Ocean-Side Villa Tranquility
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Villa in Cole Bay, Sint Maarten
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
3–8 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Villa in Little Bay, Sint Maarten
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 104 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
1–6 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 47 reviews