Vacation Rentals & Villas in Simpson Bay

/ Home
/ Vacation Rentals
/ Caribbean
/ St. Martin Sint Maarten
/ Sint Maarten
/ Simpson Bay
Book with confidence.

Updating...

age 0-16
337 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

337 villas

Why am I receiving these results?

Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$213

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Housekeeping Included

All filters match

Price per night from

$660

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$198

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$213

COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$230

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

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Housekeeping Included

All filters match

Price per night from

$918

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$230

Match: Housekeeping Included

All filters match

Price per night from

$560

BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included

All filters match

Price per night from

$502

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Match: Housekeeping Included

All filters match

Price per night from

$2,435

COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$230

Modern Luxury Directly on the Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 28 minutes

Match: Housekeeping Included

All filters match

Price per night from

$316

Match: Housekeeping Included

All filters match

Price per night from

$673

CASA DE BELLA... Great location at a great price!!

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included

All filters match

Price per night from

$216

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

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Housekeeping Included

All filters match

Price per night from

$430

The Sapphire: Turquoise Suite - Tranquility!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$213

RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$443

Beach Heaven

Simpson Bay penthouse

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$345

EL Zafiro: Emerald Suite - A Gem within a Gem!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$391

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

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Housekeeping Included

All filters match

Price per night from

$230

ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Housekeeping Included

All filters match

Price per night from

$273

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$510

Sapphire Suite - Indulgent retreat!

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$220

Sapphire: Peridot Suite - Iconic Views

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Housekeeping Included

All filters match

Price per night from

$198

Match: Housekeeping Included

All filters match

Price per night from

$358

Coco Beach House

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$447

BEACH SECRET... Modern 4 BR beauty on Burgeaux Bay, walk to Maho!

Simpson Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Housekeeping Included

All filters match

Price per night from

$1,149

Match: Housekeeping Included

All filters match

Price per night from

$1,800

Coco Beach Duplex

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$263

Hamaka condo, a beachfront retreat on Simpson Bay Beach

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Housekeeping Included

All filters match

Price per night from

$230

C-SCAPE CONDO... Beautiful, Modern, Affordable 2BR Directly on Beach!

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$301

Atrium Beach Resort and Spa 2BR

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Housekeeping Included

All filters match

Price per night from

$206

FAJA LOBIE... Completely Updated Beachfront Villa on Burgeoux Bay

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included

All filters match

Price per night from

$559

Match: Housekeeping Included

All filters match

Price per night from

$287

BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Heated Pool!

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Housekeeping Included

All filters match

Price per night from

$2,807

COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Housekeeping Included

All filters match

Price per night from

$391

Match: Housekeeping Included

All filters match

Price per night from

$484

Great rentals within 20 miles that match your search

3BDRM Beautiful Condo at Westin Dawn Beach Club

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Housekeeping Included

All filters match

Price per night from

$616

Viewing 38 of 337
rentals in Simpson Bay

×

Also consider