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Search results; Over 1,000 homes in Simpson Bay

Top guest favorite
Guesthouse in Simpson Bay, Sint Maarten
Roof deck with 360° ocean views
1 bedroom, 1 bed, 1 private bath
Aug 14 – 19
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4.95 out of 5 average rating, 108 reviews
Guest favorite
Home in Lowlands, Sint Maarten
Rooftop terrace with lagoon views and pool
4.88 out of 5 average rating, 26 reviews, 2 bedrooms, 3 beds, 2.5 baths
Aug 15 – 20
Superhost
Condo in Upper Prince's Quarter, Sint Maarten
270° ocean views from a private terrace
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 2.5 baths
Sep 4 – 9
Top guest favorite
Loft in Marigot, St. Martin
Sea views and a private pool
4.99 out of 5 average rating, 198 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 14 – 19
Top guest favorite
Villa in Philipsburg, Sint Maarten
Infinity pool overlooking the Caribbean Sea
4.99 out of 5 average rating, 331 reviews, 3 bedrooms, 4 beds, 3 baths
Apr 10 – 15
Townhouse in Simpson Bay, Sint Maarten
Beach access with Caribbean sunset balconies
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2.5 baths
Sep 8 – 13
Guest favorite
Apartment in Simpson Bay, Sint Maarten
Renovated loft with pools and a hot tub
5.0 out of 5 average rating, 80 reviews, 2 beds, 1.5 baths
Sep 7 – 12
Top guest favorite
Apartment in Simpson Bay, Sint Maarten
Oceanfront boho décor with a private rooftop
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 14 – 21
Top guest favorite
Villa in Sint Maarten, Sint Maarten
Oceanfront with panoramic Caribbean views
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 3 beds, 3.5 baths
Aug 21 – 26
Home in Koolbaai, Sint Maarten
Oceanfront villa with a private plunge pool
New place to stay, 2 bedrooms, 2 beds, 2.5 baths
Aug 16 – 21
Top guest favorite
Condo in Simpson Bay, Sint Maarten
Beachfront with a private pool and terrace
4.96 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 4 baths
Sep 6 – 11
Guest favorite
Apartment in Lowlands, Sint Maarten
Walk to Maho Beach with pool
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bath
Sep 5 – 10
Top guest favorite
Home in Koolbaai, Sint Maarten
Beachfront villa with a private pool
5.0 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 3.5 baths
Sep 27 – Oct 2
Superhost
Apartment in Saint Martin, St. Martin
Renovated with a sea-facing terrace
New place to stay, 1 bedroom, 1 bed, 1 bath
Sep 6 – 11
Top guest favorite
Apartment in Simpson Bay, Sint Maarten
Beachfront with a hardwood sun deck
5.0 out of 5 average rating, 250 reviews, 1 bedroom, 1 bed, 1.5 baths
Sep 24 – 29
Top guest favorite
Room in Upper Prince's Quarter, Sint Maarten
1BR Luxury Apartment | Ocean View
5.0 out of 5 average rating, 14 reviews, 1 king bed, 1.5 baths
Aug 28 – Sep 2
Guest favorite
Apartment in Little Bay, Sint Maarten
Ocean-view terrace with a private heated pool
4.99 out of 5 average rating, 186 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 8 – 13
Top guest favorite
Apartment in Grand Cayes, St. Martin
Panoramic ocean view near Pinel Island
5.0 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bath
Aug 26 – 31
Top guest favorite
Room in Simpson Bay, Sint Maarten
Walk to 4 beaches from Maho
5.0 out of 5 average rating, 8 reviews, 1 double bed, 1 bath
Aug 15 – 20