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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Flat in Simpson Bay, Sint Maarten
Second Home Beach Apartment
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.99 out of 5 average rating, 102 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
5.0 out of 5 average rating, 64 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
5.0 out of 5 average rating, 246 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 3 bathrooms
9–14 Aug
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
5.0 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul
Guest favourite
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
4.87 out of 5 average rating, 262 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach 2
4.85 out of 5 average rating, 201 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Flat in Cole Bay, Sint Maarten
Luxurious Sunset Lagoon View
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
4–9 Aug
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
4.9 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 3 bathrooms
2–7 Aug
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
5.0 out of 5 average rating, 76 reviews, 2 beds, 1.5 bathrooms
5–10 Oct
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
4.97 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
16–21 Oct
Top guest favourite
Apartment in Lowlands, Sint Maarten
Saint Maarten La Terrasse Maho
4.95 out of 5 average rating, 134 reviews, 2 beds, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
Guest favourite
Flat in Grand-Case, St Martin
NEW: Unmatched Oceanfront Living in Grand Case
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
SkyPort Condo
4.97 out of 5 average rating, 79 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
16–21 Jul
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Paradise with Pool & Stunning Sunsets
4.9 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
Guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4.97 out of 5 average rating, 86 reviews, 4 bedrooms, 4 beds, 4 bathrooms
9–14 Sept
Top guest favourite
Guest house in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
4.95 out of 5 average rating, 108 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Aug