Beachfront holiday rentals in Simpson Bay
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Top-rated beachfront rentals in Simpson Bay
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for beachfront rentals in Simpson Bay
Pet-friendly beachfront home rentals
Flat in Lowlands, Sint Maarten
4.97 out of 5 average rating, 113 reviewsCupecoy Garden Side
15–22 Nov
Apartment in Saint Martin , St. Martin
4.86 out of 5 average rating, 109 reviews2 Bedroom Duplex up to 5 guests right on the beach
20–27 Apr
Flat in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 3 reviewsThe Loft at Simpson Bay Yacht Club
14–21 Aug
Home in Collectivité de Saint-Martin, St. Martin
4.88 out of 5 average rating, 32 reviews"Salty Beach" - Amazing 1 bedroom beachfront
10–17 Sept
Apartment in Collectivity of Saint Martin, St. Martin
4.89 out of 5 average rating, 37 reviewsApartment Canelle
16–23 May
Flat in Pelican Key, Sint Maarten
4.83 out of 5 average rating, 29 reviewsGated Oasis in Pelican Key
17–24 Jul
Townhouse in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 72 reviewsHillside Beach Townhouse Simpson Bay
19–26 Sept
Flat in Simpson Bay
4.89 out of 5 average rating, 46 reviewsSimpson Bay apartment-free parking, great location
26 Mar – 2 Apr
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
21–28 Oct
Apartment in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 56 reviewsBeach front luxury! Huge 2BR that has it all! 😍🤩😍
29 Mar – 5 Apr
Apartment in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 29 reviewsEncanto -2BR beachfront w/pool & gorgeous sunsets!
21–28 Nov
Flat in Lowlands, Sint Maarten
4.83 out of 5 average rating, 18 reviewsThe Emerald at Maho
28 Mar – 4 Apr
Flat in Lowlands
5.0 out of 5 average rating, 16 reviewsRock Star Gem in Maho
21–28 Oct
Apartment in Simpson Bay, Sint Maarten
4.96 out of 5 average rating, 72 reviewsFive Star Luxury Beachfront Condo Private Hot Tub
9–16 Nov
Flat in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 45 reviewsHARMONY HAVEN on Simpson Bay Beach Beacon Hill
20–27 May
Guest house in Cole Bay, Sint Maarten
4.96 out of 5 average rating, 24 reviewsNew! Apartment with ocean view#4
14–21 Jan
Private beachfront home rentals
Apartment in Simpson Bay, Sint Maarten
4.94 out of 5 average rating, 18 reviewsBeachside Escape
26 Oct – 2 Nov
Apartment in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 28 reviewsOCEAN FRONT Steps From BEACH!
18–25 Feb
Apartment in Simpson Bay, Sint Maarten
4.97 out of 5 average rating, 36 reviewsHamaka condo, a beachfront retreat on Simpson Bay
20–27 Mar
Apartment in Maho Beach, Sint Maarten
4.81 out of 5 average rating, 21 reviewsVilla Spice For Life SXM
14–21 Dec
Flat in Simpson Bay
5.0 out of 5 average rating, 26 reviewsLe Papillon -Modern, beachfront, 550sq. ft terrace
1–8 Aug
Flat in Lowlands, Sint Maarten
4.94 out of 5 average rating, 17 reviewsA Maho Studio
8–15 Jun
Flat in Cole Bay, Sint Maarten
4.95 out of 5 average rating, 22 reviewsRoyal Palm Hilton SXM
7–14 Jun
Apartment in Saint Martin,Guadeloupe, St. Martin
5.0 out of 5 average rating, 26 reviewsVilla Belharra, amazing view
15–22 Jul
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
£64 before taxes and fees
Destinations to explore
- Orient Bay Holiday rentals
- Grand Case Holiday rentals
- Gustavia Holiday rentals
- Philipsburg Holiday rentals
- Bakers Bay Holiday rentals
- Baie Nettlé Holiday rentals
- Maho Beach Holiday rentals
- Marigot Holiday rentals
- Cul-de-Sac Holiday rentals
- Mont Vernon Holiday rentals
- Anse Marcel Holiday rentals
- San Juan Holiday rentals
- Beachfront rentals Saint Martin
- Beachfront rentals Sint Maarten
- Beachfront rentals Sint Maarten
- Beachfront rentals Saint Barthélemy
- Apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- House rentals Simpson Bay
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- Family-friendly rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with a washing machine and dryer Simpson Bay
- Villa rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Flat rentals Simpson Bay
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- Serviced apartment rentals Simpson Bay
- Beach apartment rentals Simpson Bay
- Family-friendly rentals Simpson Bay
- Monthly Rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
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