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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.

Filtering by: Jacuzzi or hot tub

Great rentals within 20 miles that match your search

1 / 21

Bonne View Villa #2

  • 4
  • 10
  • 1 night min

$701

Details

1 / 25

KISHTI VILLA - Blackgarden Bay, Anguilla

  • 1
  • Min stay varies

Inquire for Rates

Details

1 / 25

INCREDIBLE VALUE! Oceanfront Beaches Edge East Villa

  • 5
  • 12
  • Min stay varies

$1400

Details

1 / 14

FOUR SEASONS PRIVATE RESIDENCES - SUITES B*******, West End, Anguilla

  • 2
  • 1
  • Min stay varies

Inquire for Rates

Details

1 / 48

JASMIN... short walk to beautiful Plum Baie beach... has a gym too!

  • 5
  • 10
  • Min stay varies

$1144

Details

1 / 15

SHERIVA INFINITY, West End Anguilla

  • 8
  • 1
  • Min stay varies

$6001

Details

1 / 19

CASA LINDA... a unique hillside 3BR villa with great views of Oyster Pond

  • 3
  • 6
  • Min stay varies

$366

Details

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BLUE RESIDENCE 707 A & B... luxury living on St Maarten's

  • 3
  • 6
  • Min stay varies

$322

Details

1 / 22

THE BLUE HOUSE - Little Harbour, Anguilla

  • 10
  • 1
  • Min stay varies

$8601

Details

1 / 24

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

  • 3
  • 8
  • Min stay varies

$480

Details

1 / 22

Carisma on the beach

  • 2
  • 4
  • Min stay varies

$275

Details

1 / 18

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

  • 3
  • 6
  • Min stay varies

$279

Details

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

  • 6
  • 22
  • 5 nights min

$1801

Details

1 / 23

Aqualina 102

  • 2
  • 4
  • Min stay varies

$414

Details

1 / 33

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

  • 7
  • 14
  • Min stay varies

$1201

Details

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SIMPSON BAY BEACH CONDO #2...located right on the beach at beautiful Simpson Bay

  • 2
  • 4
  • Min stay varies

$258

Details

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Beautiful 5 bedroom contemporary villa

  • 5
  • 10
  • 5 nights min

$1230

Details

1 / 10

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

  • 5
  • 8
  • Min stay varies

$1072

Details

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

  • 3
  • 6
  • Min stay varies

$343

Details

1 / 41

The Reef at Simpson Bay, Saint Maarten - Private Pool, Ocean Views, Modern

  • 5
  • 10
  • Min stay varies

$1144

Details

1 / 5

Luxury 2 bedroom with private beach access & hot tub

  • 2
  • 4
  • 5 nights min

$425

Details

1 / 38

SEA BEACH TREASURE...Gorgeous 2BR Penthouse on Simpson Bay Beach, St Maarten

  • 2
  • 4
  • Min stay varies

$265

Details

1 / 16

ST TROPEZ... amazing views of Heineken Regatta from this beautiful villa in

  • 3
  • 6
  • Min stay varies

$501

Details

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COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay

  • 2
  • 4
  • Min stay varies

$273

Details

1 / 25

MARISOL...light and airy townhouse at Point Blue in Pelican Key Estate

  • 2
  • 4
  • Min stay varies

$258

Details

1 / 29

SMART VILLA...nestled beachfront at Pelican Key

  • 3
  • 6
  • Min stay varies

$258

Details

1 / 30

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

  • 3
  • 6
  • Min stay varies

$336

Details

1 / 13

COLONY MANOR GUEST COTTAGE... romantic hideaway right on Simpson Bay Beach!

  • Studio
  • 2
  • Min stay varies

$201

Details

1 / 29

ATLANTIS...* COCO BEACH CLUB...Located right on the beach at Simpson Bay!

  • 1
  • 2
  • Min stay varies

$229

Details

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La Perla Estate at Terres Basses, Saint Maarten - Oceanfront, Luxury, Private

  • 5
  • 10
  • Min stay varies

Inquire for Rates

Details

1 / 61

WITENBLAUW... Magical Beach Front Estate on Pelican Key

  • 6
  • 12
  • Min stay varies

$1801

Details

1 / 31

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

  • 5
  • 10
  • Min stay varies

$644

Details

1 / 10

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

  • 3
  • 8
  • 6 nights min

$501

Details

1 / 38

SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to

  • 5
  • 10
  • Min stay varies

$429

Details

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