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Areas near Simpson Bay

Travelers going to Simpson Bay are booking December dates now. Secure your vacation rental today and have the perfect trip.

1 / 22

Villa Velaire, Oceanfront Villa with Private Pool

  • 2
  • 4
  • Min stay varies

$207

Details

1 / 22

Carisma on the beach

  • 2
  • 4
  • Min stay varies

$275

Details

1 / 24

Le Papillon - Modern Beachfront Unit, stunning view, great amenities

  • 2
  • 6
  • Min stay varies

$285

Details

1 / 34

Caribbean Sun

  • 2
  • 4
  • 6 nights min

$300

Details

1 / 12

Blue Pelican Luxury Villas - Featured on HGTV!!!!!

  • 1
  • 2
  • Min stay varies

$109

Details

1 / 12

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

  • 1
  • 2
  • Min stay varies

$125

Details

1 / 32

Simpson Bay Beach Modern Luxury Ocean View 1 BR

  • 1
  • 4
  • 4 nights min

$145

Details

1 / 24

Le Papillon Penthouse - Stunning, modern beachfront unit with private roof top

  • 3
  • 8
  • Min stay varies

$480

Details

1 / 17

Perfect Pelican Escape -- Spectacular Views & Best Sunset Happy Hour

  • 2
  • 4
  • Min stay varies

$125

Details

1 / 17

Beachfront gated Condo directly on Simpson Bay

  • 2
  • 5
  • Min stay varies

$250

Details

1 / 25

Beach Front Property - Amazing Sunset

  • 5
  • 12
  • Min stay varies

$701

Details

1 / 23

5 Bed 5 Bathrooms Beach Front - Spectacular Sunset

  • 5
  • 12
  • Min stay varies

$701

Details

1 / 21

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

  • 2
  • 4
  • Min stay varies

$450

Details

1 / 22

Beach Front Property - Spectacular Sunset

  • 5
  • 16
  • Min stay varies

$851

Details

1 / 15

BEACHFRONTBLISS

  • 2
  • 4
  • Min stay varies

$250

Details

1 / 9

Coco Beach #5 ON THE BEACH

  • 2
  • 6
  • 1 night min

$372

Details

1 / 32

Barefoot Oceanfront Condo St Maarten

  • 2
  • 6
  • 4 nights min

$305

Details

1 / 33

Steps to Caribbean, pool and 2 mile-long beach

  • 1
  • 2
  • 7 nights min

$226

Details

1 / 9

Beachfront Condo

  • 2
  • 4
  • 5 nights min

$516

Details

1 / 21

2 Bedrooms 2 Bathrooms Cliffside Villa - Bay Views

  • 2
  • 4
  • Min stay varies

$280

Details

1 / 8

Pelican Key 1Bedroom For Rent

  • 1
  • 4
  • Min stay varies

$200

Details

1 / 18

Anchorage Apartment

  • 1
  • 4
  • Min stay varies

$150

Details

1 / 22

5 Bedrooms 4 Bathrooms - Spectacular Sunset Views

  • 5
  • 12
  • Min stay varies

$501

Details

1 / 17

Pearl on the Beach

  • 2
  • 4
  • 5 nights min

$516

Details

1 / 20

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

  • 2
  • 4
  • 7 nights min

$214

Details

1 / 22

PEARL Beach Residence at El Zafiro

  • 1
  • 4
  • 3 nights min

$216

Details

1 / 5

Luxury 2 bedroom with private beach access & hot tub

  • 2
  • 4
  • 5 nights min

$425

Details

1 / 21

Cool Bay Villa St Maarten

  • 2
  • 4
  • 6 nights min

$89

Details

1 / 16

Tres Belle Villa

  • 2
  • 5
  • 5 nights min

$196

Details

1 / 9

Beautiful Studio in Pelican Key /Simpson Bay

  • 1
  • 2
  • 1 night min

$90

Details

1 / 65

WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`

  • 3
  • 7
  • Min stay varies

$401

Details

1 / 21

The Sapphire: Turquoise Suite - Tranquility!

  • 1
  • 4
  • 3 nights min

$140

Details

1 / 11

Studio in Pelican Key Paradise

  • 2
  • 3 nights min

$150

Details

1 / 10

3 bdrm 3 bath Villa on the beach in st. maarten

  • 3
  • 8
  • 6 nights min

$501

Details

1 / 23

Brand New House Indigo Bay beach, St Maarten

  • 3
  • 6
  • 1 night min

$468

Details

1 / 20

Ruby Beach Residence at El Zafiro

  • 1
  • 4
  • 3 nights min

$216

Details

1 / 33

Villa Vita on the beach St Maarten,Caribbean

  • 3
  • 6
  • Min stay varies

$423

Details

1 / 23

Ocean front 30 feet from the stunning blue Ocean

  • 2
  • 4
  • 5 nights min

$176

Details

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