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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
16–21 Oct
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4.97 out of 5 average rating, 106 reviews
Apartment in Philipsburg, Sint Maarten
Flamingo Beach by Hilton Grand Vacations- studio
1 bathroom
12–17 Sept
Top guest favourite
Home in Simpson Bay, Sint Maarten
Villa Blue View .. stunning views of endless sea!
5.0 out of 5 average rating, 91 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Home in Koolbaai, Sint Maarten
Bahia - Villa 1
3 bedrooms, 3 beds, 2.5 bathrooms
21–28 Jul
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Simpson bay beach, spacious, beautiful views!
5.0 out of 5 average rating, 152 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 3 bathrooms
9–14 Aug
Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
4.99 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Cole Bay, Sint Maarten
Beautiful, bright apartment with a lagoon view in Simpson Bay
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Aug
Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
Flat in Simpson Bay, Sint Maarten
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Jul
Guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4.97 out of 5 average rating, 86 reviews, 4 bedrooms, 4 beds, 4 bathrooms
7–12 Jul
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Pineapple Suite
4.95 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Paradise with Pool & Stunning Sunsets
4.9 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
4.98 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Guest favourite
Villa in Simpson Bay, Sint Maarten
Villa Myles: Beachfront
4.79 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
Guest favourite
Apartment in Cole Bay, Sint Maarten
PARADISE ONE TO LAS BRISAS
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Aug
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
5.0 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Jul
Superhost
Serviced apartment in Simpson Bay, Sint Maarten
Unit 3 - Luxury apartment by the sea
4.84 out of 5 average rating, 51 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug