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Search results; Over 1,000 homes in Simpson Bay

Superhost
Apartment in Simpson Bay, Sint Maarten
Oceanfront w Pool | Maho Beach area
1 bedroom, 2 beds, 1.5 private bathrooms
24–30 Sept
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4.8 out of 5 average rating, 192 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 84 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
23–28 Sept
4.91 out of 5 average rating, 58 reviews
Guest favourite
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
24–29 Sept
4.87 out of 5 average rating, 275 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
14–19 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 69 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
Superhost
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed, 1 bathroom
8–13 Oct
4.87 out of 5 average rating, 142 reviews
Townhouse in Simpson Bay, Sint Maarten
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Villa in Little Bay, Sint Maarten
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.99 out of 5 average rating, 105 reviews
Guest favourite
Flat in Maho Beach, Sint Maarten
Escapes at the Emerald – Airport & Beach Nearby
Individual host
16–21 Nov
4.93 out of 5 average rating, 27 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
10–15 Mar
4.96 out of 5 average rating, 109 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and swimming pool access
Individual host
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Cole Bay, Sint Maarten
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
15–20 Oct
4.95 out of 5 average rating, 21 reviews
Guest favourite
Flat in Lowlands, Sint Maarten
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.91 out of 5 average rating, 11 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.85 out of 5 average rating, 55 reviews
Flat in Saint-Martin, St Martin
Large 1-bedroom apartment with sea view and beach access - Baie Nettlé
Business host
14–19 Sept
New place to stay
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds, 3.5 bathrooms
3–8 Oct
4.98 out of 5 average rating, 47 reviews