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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds, 1 private bathroom
3–8 Sept
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4.95 out of 5 average rating, 106 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds
4–9 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
3–8 Sept
5.0 out of 5 average rating, 82 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Royal Palm Hilton SXM
2 bedrooms, 3 beds
5–12 Sept
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Villa in Little Bay, Sint Maarten
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds
6–11 Sept
4.99 out of 5 average rating, 104 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed
17–22 Sept
4.96 out of 5 average rating, 76 reviews
Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Stunning Boho-Chic Beach Condo with Rooftop
2 bedrooms, 2 beds
11–16 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Cupecoy, Sint Maarten
Stunning oceanfront condo
2 bedrooms, 2 king beds
15–20 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds
1–6 Oct
4.92 out of 5 average rating, 26 reviews
Guest favourite
Apartment in Little Bay, Sint Maarten
Maazoon -Luxury modern 3BR Apt for 6 – Central SXM
3 bedrooms, 5 beds
8–13 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Top guest favourite
Apartment in Maho, Sint Maarten
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed
3–8 Sept
4.91 out of 5 average rating, 257 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
SeaViews 2Brm Ocean Front Condo SXM
2 bedrooms, 2 beds
13–18 Sept
4.91 out of 5 average rating, 34 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds
11–16 Sept
4.99 out of 5 average rating, 335 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds
16–21 Oct
4.96 out of 5 average rating, 109 reviews