Beachfront vacation rentals in Simpson Bay
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Simpson Bay
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Simpson Bay beachfront rentals
Beachfront home rentals with a pool
Villa in Cul-de-Sac, St. Martin
4.98 out of 5 average rating, 101 reviewsVILLA JADE 2: WATERFRONT/ POOL
Oct 21 – 28
Apartment in Lowlands, Sint Maarten
4.83 out of 5 average rating, 18 reviewsThe Emerald at Maho
Aug 13 – 20
Condo in Lowlands
4.94 out of 5 average rating, 89 reviewsSint Maarten La Terrasse Maho
Apr 25 – May 2
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 29 reviewsEncanto -2BR beachfront w/pool & gorgeous sunsets!
Dec 16 – 23
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 16 reviewsRock Star Gem in Maho
Oct 22 – 29
Condo in Simpson Bay
4.96 out of 5 average rating, 72 reviewsFive Star Luxury Beachfront Condo Private Hot Tub
Nov 3 – 10
Condo in Saint Martin,Guadeloupe, St. Martin
5.0 out of 5 average rating, 26 reviewsVilla Belharra, amazing view
Oct 5 – 12
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 13 reviewsPopular Beachfront Property Barefoot /Simpson bay
Oct 12 – 19
Beachfront home rentals with a hot tub
Guest suite in Cole Bay, Sint Maarten
4.94 out of 5 average rating, 160 reviewsIndigo Sweet
Jan 1 – 8
Apartment in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 4 reviewsA103 - Incredible Apartment with Garden
Oct 6 – 13
Condo in Simpson Bay, Sint Maarten
4.9 out of 5 average rating, 10 reviewsLovely Lagoon Townhouse SBYC
Oct 6 – 13
Apartment in Simpson Bay, Sint Maarten
4.96 out of 5 average rating, 93 reviewsTop of the art penthouse
Apr 21 – 28
Home in Lowlands, Sint Maarten
4.9 out of 5 average rating, 69 reviewsSapphire Fantasy : Oceanfront paradise
Jan 11 – 18
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 5 reviews1 bedroom paradise
Aug 18 – 25
Villa in Little Bay, Sint Maarten
5.0 out of 5 average rating, 17 reviewsBarefoot Villas
Nov 3 – 10
Condo in Lowlands, Sint Maarten
5.0 out of 5 average rating, 27 reviewsThe Cliff in Cupecoy Beach HEAVEN!!!
Mar 26 – Apr 2
Pet-friendly beachfront home rentals
Apartment in Lowlands, Sint Maarten
4.97 out of 5 average rating, 113 reviewsCupecoy Côté Jardin
Nov 15 – 22
Condo in Saint Martin , St. Martin
4.86 out of 5 average rating, 109 reviews2 Bedroom Duplex up to 5 guests right on the beach
Apr 21 – 28
Condo in Collectivity of Saint Martin, St. Martin
4.89 out of 5 average rating, 37 reviewsApartment Canelle
May 17 – 24
Home in Collectivité de Saint-Martin, St. Martin
4.88 out of 5 average rating, 32 reviews"Salty Beach" - Amazing 1 bedroom beachfront
Sep 11 – 18
Townhouse in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 72 reviewsHillside Beach Townhouse Simpson Bay
Oct 23 – 30
Apartment in Simpson Bay, Sint Maarten
4.89 out of 5 average rating, 46 reviewsSimpson Bay apartment-free parking, great location
Mar 27 – Apr 3
Condo in Lowlands, Sint Maarten
4.97 out of 5 average rating, 33 reviewsGorgeous Beachfront PENTHOUSE- Sunset Ocean Views!
Sep 18 – 25
Apartment in Sint Maarten, Sint Maarten
5.0 out of 5 average rating, 13 reviewsCOndostmaarten panoramic
Aug 7 – 14
Quick stats about beachfront rentals in Simpson Bay
Total rentals
110 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5K reviews
Nightly prices starting at
$80 before taxes and fees
Destinations to explore
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- Rentals with outdoor seating Simpson Bay
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- Rentals with a patio Simpson Bay
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- Rentals with a washer and dryer Simpson Bay
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- Kid-friendly rentals Simpson Bay
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