Simpson Bay Vacation Rentals, House Rentals & more


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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 / 10

2BR-Oceanfront-Royal Palm

  • 2
  • 6
  • Min stay varies

$348

Details

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La Casita - Ideal for Couples and Families, Beautiful Pool and Beach

  • 3
  • 6
  • Min stay varies

$356

Details

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

  • 2
  • 6
  • Min stay varies

$283

Details

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IL PUNTO BLUE...located right on the beach in prestigious Pelican Key

  • 3
  • 6
  • Min stay varies

$214

Details

1 / 33

BELLA VITA... a gorgeous, 7BR super deluxe... views galore

  • 7
  • 14
  • Min stay varies

$1191

Details

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Steps to Caribbean, pool and 2 mile-long beach

  • 1
  • 2
  • 7 nights min

$224

Details

1 / 48

Villa Balaclava - Luxury villa " MAGNIFIQUE & Full Privacy "

  • 5
  • 10
  • Min stay varies

$512

Details

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Caribbean Sun

  • 2
  • 4
  • 6 nights min

$298

Details

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BEACHSIDE CONDO... you can't get much closer to the beach than this!!

  • 3
  • 6
  • Min stay varies

$277

Details

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Villa Amaryllis 4 + 1 Bedroom (The Villa Is Located In A Gated Residence Just

  • 5
  • 10
  • Min stay varies

$780

Details

1 / 12

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

  • 1
  • 2
  • Min stay varies

$124

Details

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Villa Vista - Ideal for Couples and Families, Beautiful Pool and Beach

  • 5
  • 10
  • Min stay varies

$539

Details

1 / 10

Daffodil at Pelican Key, Saint Maarten - Beachfront, Gated Community, Pool

  • 5
  • 8
  • Min stay varies

$1063

Details

1 / 50

Beautiful 5 bedroom contemporary villa

  • 5
  • 10
  • 5 nights min

$1219

Details

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Villa La-Di-Da at Pelican Key, Saint Maarten - Spectacular Ocean View, Infinity

  • 6
  • 12
  • Min stay varies

$851

Details

1 / 21

2 Bedrooms 2 Bathrooms Cliffside Villa - Bay Views

  • 2
  • 4
  • Min stay varies

$278

Details

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Carisma on the beach

  • 2
  • 4
  • Min stay varies

$273

Details

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Villa Velaire, Oceanfront Villa with Private Pool

  • 2
  • 4
  • Min stay varies

$206

Details

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Caribbean Blue - Ideal for Couples and Families, Beautiful Pool and Beach

  • 5
  • 2
  • Min stay varies

$639

Details

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The Sapphire: Aquamarine Suite- Breathtaking views!

  • 1
  • 4
  • 3 nights min

$148

Details

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Witenblauw Estate at Pelican Key, Saint Maarten - Directly On The Beach

  • 6
  • 22
  • 5 nights min

$1787

Details

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Sur Mer at Simpson Bay, Saint Maarten - Beachfront Gated Community, Pool

  • 3
  • 6
  • Min stay varies

$411

Details

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Beach Front Property - Spectacular Sunset

  • 5
  • 16
  • Min stay varies

$844

Details

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The Sapphire: Pearl Suite - Peace of mind!

  • 1
  • 4
  • 3 nights min

$138

Details

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Villa Hardman

  • 5
  • 10
  • Min stay varies

$844

Details

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Colony Manor

  • 1
  • 2
  • Min stay varies

$199

Details

1 / 17

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

  • 2
  • 4
  • Min stay varies

$125

Details

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1 Bed Luxury Condo

  • 1
  • 2
  • Min stay varies

$100

Details

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

  • 3
  • 8
  • Min stay varies

$477

Details

1 / 19

SUR MER * Coco's Beach Club... gorgeous beach front condo on beautiful Simpson

  • 3
  • 6
  • Min stay varies

$343

Details

1 / 23

Aqualina 102

  • 2
  • 4
  • Min stay varies

$411

Details

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Bella Vita - Ideal for Couples and Families, Beautiful Pool and Beach

  • 7
  • 14
  • Min stay varies

$1501

Details

1 / 32

Simpson Bay Beach Modern Luxury Ocean View 1 BR

  • 1
  • 4
  • 4 nights min

$145

Details

1 / 33

Faja Lobie at Beacon Hill, Saint Maarten - Beachfront & Pool

  • 3
  • 6
  • Min stay varies

$413

Details

1 / 18

Simpson Bay Yacht Club Condo - Unit 6

  • 2
  • 4
  • 3 nights min

$157

Details

1 / 12

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

  • 1
  • 2
  • Min stay varies

$109

Details

Recent reviews for Simpson Bay

"Amazing Spot!!!!"

Left on 06/20/2017 for a stay in June 2017
My husband and I stayed a week at the El Zafiro. When I tell you in was the most relaxing vacation we had taken before. Nicole & Jessica was Great. I felt right at home. The service was awesome the rooms was neat and clean. Nicole goes out of her way to make you feel special whatever you need if she can help you she will in letting you know the best tourists spots,as well as shopping and places to eat. My husband and our guest enjoyed the food as well as talking to Jess. If you are looking for a nice friendly spot look No Further this is it. We really enjoyed ourselves. This is the place to be El ZaFiro. Lloyd & Sara

"Amazing!!!!!"

Left on 06/20/2017 for a stay in June 2017
Had a amazing time at El ZaFiro. If you are looking for a nice quiet and friendly place this is it and away from the hustle and bustle of the busy city again this is it. It's a must to visit and stay at the El Zafiro. Thumbs up to Nicole & Ed

"Lights out"

Left on 12/04/2016 for a stay in November 2016
Villa La Luna is located beachside. There isn't much beach space but what's there is nice. Large pool and deck space. Beautiful sunsets right from the deck every night. The house could be fabulous with a few minor repairs. Lots of light bulbs out, the upstairs bathroom leaked in to the downstairs kitchen, one of the bedroom doors was extremely difficult to open, one exterior door did not lock. The home is roomy and with ten adults you could always find a quiet space. Televisions didn't work for the first few days of our stay. Concierge: My husband and I had airport pickup from the concierge prior to arrival, that didn't happen. Our group had also compiled a list of items (food/beverage) that we wanted to be at the home prior to arrival this also did not happen. The night before our departure we lost power for three hours. We were told that this was a scheduled power outage and that the owners knew about... this was not conveyed to our party. Losing power mid-meal prep the night before you leave is not fun.
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