Over 1,000 places in Simpson Bay

Guest favorite
Apartment in Simpson Bay
Lilly's Beach
On Maho BeachSea views,
May 10 – 15
4.97 out of 5 average rating, 154 reviews
Guest favorite
Condo in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
On Maho BeachOcean views,
Apr 30 – May 5
5.0 out of 5 average rating, 55 reviews
Superhost
Apartment in Simpson Bay
Apartment on the beach 3
On the beach
Apr 19 – 24
4.79 out of 5 average rating, 92 reviews
Guest favorite
Apartment in Simpson Bay
Ocean's Edge
May 18 – 23
5.0 out of 5 average rating, 27 reviews
Superhost
Apartment in Simpson Bay
Steps to the Beach! 2024 Modern Boho!
2 king beds
Apr 19 – 24
New place to stay
Guest favorite
Apartment in Simpson Bay
The Beach House Apartment
On Maho BeachKayak, Sea views,
Jul 31 – Aug 5
5.0 out of 5 average rating, 171 reviews
Guest favorite
Apartment in Simpson Bay
Simpson bay beach, spacious, beautiful views!
On the beachKayak, Sea views,
May 4 – 9
5.0 out of 5 average rating, 105 reviews
Guest favorite
Apartment in Simpson Bay
The Bay at Palm Beach
2 beds
May 12 – 17
5.0 out of 5 average rating, 27 reviews
Superhost
Apartment in Simpson Bay
Le Petit Paradis - Beachfront 1 Bedroom Apartment
On Maho Beach
Apr 26 – May 1
4.93 out of 5 average rating, 99 reviews
Guest favorite
Apartment in Simpson Bay
The luxe 1 bedroom apt with pool
1 king bed
Apr 19 – 24
5.0 out of 5 average rating, 24 reviews
Guest favorite
Apartment in Simpson Bay
At the Beach: Beachfront Oasis
1 bed
May 15 – 20
5.0 out of 5 average rating, 9 reviews
Guest favorite
Apartment in Simpson Bay
Modern / Cozy Studio in the center of Simpson Bay
2 beds
May 5 – 10
5.0 out of 5 average rating, 13 reviews
Guest favorite
Condo in Simpson Bay
Encanto -2BR beachfront w/pool & gorgeous sunsets!
3 beds
Jul 11 – 16
5.0 out of 5 average rating, 29 reviews
Guest favorite
Condo in Simpson Bay
Beachfront Caribbean Breeze in Paradise, SXM
2 king beds
May 1 – 6
5.0 out of 5 average rating, 14 reviews
Guest favorite
Condo in Simpson Bay
OCEAN FRONT Steps From BEACH!
2 king beds
Apr 26 – May 1
5.0 out of 5 average rating, 27 reviews
Guest favorite
Apartment in Simpson Bay
HARMONY HAVEN on Simpson Bay Beach Beacon Hill
On the beach
Apr 22 – 27
5.0 out of 5 average rating, 44 reviews
Guest favorite
Condo in Simpson Bay
Beachside Escape
3 beds
May 4 – 9
4.94 out of 5 average rating, 18 reviews
Guest favorite
Condo in Simpson Bay
The Beach Condo
2 king beds
May 18 – 23
5.0 out of 5 average rating, 51 reviews