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Search results; Over 1,000 homes in Simpson Bay

Top 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, 109 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds
10–15 Apr
4.99 out of 5 average rating, 330 reviews
Superhost
Apartment in Upper Prince's Quarter, Sint Maarten
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds
12–17 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Indigo Bay, Sint Maarten
Luxury Villa Ocean at Indigo Bay with Private Pool
3 bedrooms, 3 beds
18–23 Oct
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds
3–8 Oct
4.98 out of 5 average rating, 43 reviews
Guest favourite
Flat in Cole Bay, Sint Maarten
Luxurious Sunset Lagoon View
2 bedrooms, 2 beds
11–16 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
1 bedroom, 1 king bed
24–29 Sept
5.0 out of 5 average rating, 250 reviews
Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds
14–19 Oct
4.99 out of 5 average rating, 198 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
7–12 Sept
4.91 out of 5 average rating, 55 reviews
Home in Koolbaai, Sint Maarten
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds
16–21 Aug
New place to stay
Top guest favourite
Villa in Cole Bay, Sint Maarten
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds
26–31 Aug
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
9–14 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 king beds
9–14 Sept
4.97 out of 5 average rating, 89 reviews
Guest favourite
Flat in Cole Bay, Sint Maarten
C354 - Top view with balcony
1 bedroom, 1 king bed
11–16 Sept
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Upper Prince's Quarter, Sint Maarten
Aman_Aria
2 bedrooms, 2 beds
5–10 Oct
4.98 out of 5 average rating, 41 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
7–12 Sept
5.0 out of 5 average rating, 79 reviews
Top guest favourite
Apartment in Maho, Sint Maarten
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed
11–16 Aug
4.91 out of 5 average rating, 252 reviews