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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.95 out of 5 average rating, 108 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
12–17 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds
13–18 Jul
5.0 out of 5 average rating, 64 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
The Beach House Apartment
1 bedroom, 1 king bed
1–6 Aug
5.0 out of 5 average rating, 245 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach 2
1 bedroom, 1 queen bed
10–15 Jul
4.85 out of 5 average rating, 200 reviews
Guest favourite
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed
28 Jul – 2 Aug
4.89 out of 5 average rating, 132 reviews
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
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds
7–12 Jul
5.0 out of 5 average rating, 39 reviews
Flat in Lowlands, Sint Maarten
Luxury Studio| Walk to Maho Beach, Casino, Dinning
1 bedroom, 1 queen bed
28 Jul – 2 Aug
New place to stay
Guest favourite
Flat in Simpson Bay, Sint Maarten
Le Petit Paradis – Beachfront 1 Bedroom Apartment
1 bedroom, 1 queen bed
9–14 Jul
4.93 out of 5 average rating, 149 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
4.97 out of 5 average rating, 106 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Top of the art penthouse
3 bedrooms, 4 beds
1–6 Aug
4.95 out of 5 average rating, 110 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, 68 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
2–7 Aug
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Lilly's Beach
1 bedroom, 1 king bed
21–26 Aug
4.95 out of 5 average rating, 236 reviews
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 55 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
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, 195 reviews