Vacation Rentals & Villas in Simpson Bay

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171 villas

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TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$660

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: Walking trips

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Price per night from

$230

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

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$917

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$230

Match: Walking trips

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Price per night from

$559

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

Match: Walking trips

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Price per night from

$2,434

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

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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: Walking trips

All filters match

Price per night from

$431

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

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$443

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$304

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

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Walking trips

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Price per night from

$273

Match: Walking trips

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Price per night from

$358

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

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

All filters match

Price per night from

$559

Infinity Views Villa SXM

Simpson Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Walking trips

All filters match

Price per night from

$195

Match: Walking trips

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Price per night from

$1,796

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

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Walking trips

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Price per night from

$2,806

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

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$391

Hamaka condo, a beachfront retreat on Simpson Bay Beach

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Walking trips

All filters match

Price per night from

$229

Great rentals within 20 miles that match your search

Suite luxueuse Saint-Martin

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Walking trips

All filters match

Price per night from

$530

TRUFFLE... Contemporty 5BR Luxury Villa with breathtaking views!!

Terres Basses house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$2,004

Ocean front "colibris" amazing view

Marigot, Saint Martin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$377

Best rated: SXM Panoramic Ocean View private villa w/exclusive private pool.

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$402

Villa Dulcinea - Ocean views, near beach, outdoor space, great for groups!

East End Village house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Walking trips

All filters match

Price per night from

$574

GRAND PALMS...Modern 3 BR villa w/ full AC, steps from Plum Baie Beach!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

All filters match

Price per night from

$817

Dawn Beach Resort, Westin Penthouse for 8 Guests!

Oyster Pond penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Walking trips

All filters match

Price per night from

$491

Gd studio dans résidence Mont Vernon vue montagne

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Walking trips

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Price per night from

$74

CARIBBEAN PARADISE... Affordable 2BR condo at Rainbow Beach Club on the shores o

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$181

AMANDARA... 20% OFF Apr, May, Jun 2024, Breathtaking Views, Heated Pool! Wow!!

Terres Basses house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Walking trips

All filters match

Price per night from

$2,234

MADRAS... Affordable 5 BR, Short walk to Plum Bay beach, Pool, Views, Full AC!

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Walking trips

All filters match

Price per night from

$574

AGUA AZUL... Gorgeous 2BR at Porto Cupecoy, great location on the Gold Coast!

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$287

COME SPEND HOLIDAY SUPER FACING THE SEA

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Walking trips

All filters match

Price per night from

$530

AZUR DREAM... 7 BR private, tropical, tranquill... great vacation villa for thos

Terres Basses villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Walking trips

All filters match

Price per night from

$1,577

LOASIS... Amazing Beachfront Estate, Spa, Gym, Heated Pool!

Terres Basses villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Walking trips

All filters match

Price per night from

$4,754

LIFE IN BLUE ... Stunning New 2 BR Luxury Beach Front Villa on Baie Rouge

Terres Basses house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Totally awesome” We stayed a Le Vie En Bleu for 10 days this last July on the advice from Ted at St. Martin Reservation Center. From the moment we stepped into this wonderful villa, we knew Ted's advice was spot on. Everything about this classy home was done with the vacationers enjoyment in mind. Granted, it's a bit small but the floor plan is designed in a way that brought your every glance to the beautiful ocean right in front of you. It had all the modern amenities you'd expect to find in a five star villa rental. My wife used the oceanfront gym each morning and loved it.I could write a novel about this totally private get away in paradise but I'll just say one thing. We plan on returning next summer to Le Vie En Bleu. Thank you Ted !!!

Match: Walking trips

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Price per night from

$1,503

JOIE DE VIVRE... 3 BR With Privacy on a fabulous Beach. WOW!

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$931

LUNE DE MIEL....The Honeymoon! Romantic hideaway for lovers

Terres Basses house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$545

CASA SAND... Gorgeous tropical hideaway! Very private and quiet!

Anse Marcel house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

All filters match

Price per night from

$541

LE CAPRICE... Spacious 7BR on Elevated Beachfront Lot, Breathtaking Views!

Terres Basses villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Walking trips

All filters match

Price per night from

$2,505

Viewing 38 of 171
rentals in Simpson Bay

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