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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Flat in Simpson Bay, Sint Maarten
Lilly's Beach
1 bedroom, 1 bed, 1 bathroom
21–26 Aug
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4.95 out of 5 average rating, 240 reviews
Superhost
Apartment in Upper Prince's Quarter, Sint Maarten
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds, 2.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 35 reviews
Guest favourite
Flat in Cole Bay, Sint Maarten
Luxurious Sunset Lagoon View
2 bedrooms, 2 beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 13 reviews
Townhouse in Simpson Bay, Sint Maarten
Tranquility @ The Drake | Just Steps to the Sand
2 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
New place to stay
Superhost
Flat in Saint Martin, St Martin
Experience a luxurious break by the sea
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
New place to stay
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 79 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 55 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Flat in Little Bay, Sint Maarten
Vibra Lux Cozy Island Escape
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
New place to stay
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
5–10 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Maho, Sint Maarten
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
6–11 Aug
4.91 out of 5 average rating, 251 reviews
Top guest favourite
Villa in Indigo Bay , Sint Maarten
AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.
4 bedrooms, 4 king beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Indigo Bay, Sint Maarten
Luxury Villa Ocean at Indigo Bay with Private Pool
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Oct
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds, 4 bathrooms
9–14 Sept
4.97 out of 5 average rating, 89 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
15–20 Aug
4.99 out of 5 average rating, 330 reviews
Top guest favourite
Flat in Cupecoy, Sint Maarten
Stunning oceanfront condo
2 bedrooms, 2 beds, 2.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Cole Bay, Sint Maarten
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 67 reviews