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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
1–6 Oct
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4.96 out of 5 average rating, 107 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 40 reviews
Top 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, 78 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
2–7 Aug
4.91 out of 5 average rating, 53 reviews
Top guest favourite
Guest house in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
4.95 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 248 reviews
Superhost
Home in Les Terres Basses, St Martin
Tiki Lodge 5mn away from the beach
3 bedrooms, 3 beds, 3 bathrooms
31 Jul – 5 Aug
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 67 reviews
Guest favourite
Home in Lowlands, Sint Maarten
Casa Rish-2BR 2.5BH TownHouse with pool in Cupecoy
2 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 23 reviews
Superhost
Room in Upper Prince's Quarter, Sint Maarten
Panorama SXM - 1 BR Ocean View - Luxury Apartment
1 king bed, 1.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Cupecoy, Sint Maarten
Stunning oceanfront condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 36 reviews
Flat in Cupecoy, Sint Maarten
Appartement de 2 chambres à Porto Cupecoy
2 bedrooms, 2 beds, 2.5 bathrooms
22–27 Jul
New place to stay
Guest favourite
Apartment in Simpson Bay, Sint Maarten
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds, 1 bathroom
26–31 Aug
4.94 out of 5 average rating, 54 reviews
Guest favourite
Flat in Cole Bay, Sint Maarten
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
31 Aug – 5 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Villa in Little Bay, Sint Maarten
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
4.99 out of 5 average rating, 98 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 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
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
4.88 out of 5 average rating, 135 reviews