10 Best Vacation Rentals in Simpson Bay Beach - Holiday Lettings - Cabins

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Simpson Bay Beach

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14 Vacation rentals

(2) Excellent 

12

Vacation apartment in Simpson Bay

Simpson Bay / Simpson Bay Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Air conditioning
Spacious studio apartment with breathtaking views for rent. Located on the island of St. Maarten in the heart of the Caribbean, this fully equipped studio, located a few minutes from all amenities is your perfect tropical getaway.Enjoy our beautiful island at its best a …see more

from $123 / night

$861 / week

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from $123 / night

(4) Excellent 

10

Vacation condo with shared pool in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Royal Palm Beach Resort in Simpson Bay is one of the most liked resorts on the island. All units face the ocean and are 2 bedrooms with a king size bed in each, and a living room with a queen size sleeper sofa. Units have full kitchens, dining room table, seating for 6, …see more

from $350 / night

$2495 / week

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from $350 / night

(4) Excellent 

24

Apartment rental in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Child friendly
Welcome in Le Papillon, the best experience on Simpson Bay beach. -Gated, private and secure community -2150 sq. feet unit -Cleaning service every third day -Private parking inside the property -40“ smart TV in each bedroom with Netflix and satellite -48“ high definit …see more

from $285 / night

$1995 - $5850 / week

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Responds fast!
avg. 1 hour 28 minutes

from $285 / night

(1) Excellent 

34

Vacation condo in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This is a great property if you if you like low key with a fantastic view. Being in the middle of Simpson Bay you can walk a mile in either direction. The property has a great pool and the beach in front is never crowded. The owner has outfitted the unit with most every …see more

from $300 / night

$2100 / week

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from $300 / night

9

Vacation condo with shared pool in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
2 Bedroom, 2.5 Bath On The Water. Luxury At Its Best!!! This contemporary 5 star resort condo is now available for your enjoyment. Located on the ground floor this unit has an amazing spacious deck just steps from the waters' edge. Feel the breeze as you sip your …see more

from $515 / night

$3605 / week

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Responds fast!
avg. 3 hours 13 minutes

from $515 / night

20

Simpson Bay Vacation apartment rental

Simpson Bay / Simpson Bay Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Ruby Residence, located in Simpson Bay, offers a view of countless miles of beautiful white sand beach and access to experience some of the Island’s great activities such as snorkeling, banana boating, jet skiing and kayaking just to name a few. It is part of our unique …see more

from $215 / night

$1505 - $2107 / week

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from $215 / night

(2) Excellent 

18

Apartment rental in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Beautiful beach side apartment with spectacular ocean view in Simpson Bay. Come stay and enjoy the beautiful sunsets and relax on the beach! Surrounded by top rated restaurants, bars, supermarkets, casino's and nightlife. Private car parking. Child friendly. …see more

from $139 / night

$973 / week

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Responds fast!
avg. 2 hours 19 minutes

from $139 / night

22

Vacation apartment with golf nearby in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Pearl Residence, located in Simpson Bay, offers a view of countless miles of beautiful white sand beach and access to experience some of the Island’s great activities such as snorkeling, banana boating, jet skiing and kayaking just to name a few. It is part of our uniqu …see more

from $215 / night

$1505 - $2107 / week

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from $215 / night

32

Vacation villa rental

Simpson Bay / Simpson Bay Beach

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Barefoot is an intimate, beachfront condo located on the water's edge of Simpson Bay Beach! This is a new, beautifully decorated 2 bedroom, 2.5 bath villa located directly on Simpson Bay Beach at Palm Beach Condos - a new intimate and well designed gated community of on …see more

from $305 / night

$2135 / week

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from $305 / night

(1) Excellent 

26

Vacation villa in Simpson Bay

Simpson Bay / Simpson Bay Beach

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Your home away from home on the Caribbean island of St. Maarten, is ideally positioned on the beach, midway between the island's most popular night spots and shopping. Fine Restaurants abound to tempt your pallet and an Activity Center makes it convenient for excursions …see more

from $143 / night

$995 / week

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Responds fast!
avg. 2 hours 53 minutes

from $143 / night

22

Vacation apartment with golf nearby in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Turquoise, located in Simpson Bay, offers a view of countless miles of beautiful white sand beach and access to experience some of the Island’s great activities such as snorkeling, banana boating, jet skiing and kayaking just to name a few. It is part of our unique bout …see more

from $215 / night

$1505 - $2107 / week

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from $215 / night

17

Vacation condo rental

Simpson Bay / Simpson Bay Beach

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
2 Bedroom, 2.5 Bath On The Water. Luxury At Its Best!!! This contemporary 5 star resort condo is now available for your enjoyment. Located on the ground floor this unit has an amazing spacious deck just steps from the waters' edge. Feel the breeze as you sip your …see more

from $515 / night

$3605 / week

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Responds fast!
avg. 3 hours 13 minutes

from $515 / night

5

Penthouse accommodation in Simpson Bay Beach with shared pool

Simpson Bay / Simpson Bay Beach

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Air conditioning
Enjoy a magnificent penthouse condominium right on golden sand Simpson Bay Beach. This is a two kilometer (1 1/4 mile) stretch of sand and Caribbean sea that is completely secluded - only private residences and small guest houses. As a result, you have an unspoiled, non …see more

from $300 / night

$2000 / week

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from $300 / night

23

Simpson Bay Beach Vacation home rental

Simpson Bay / Simpson Bay Beach

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Perfect location between Simpson Bay & Philipsburg,in the new gated community of"Indigo Bay Beach". This brand new exquisite residence, very well modern decorated & equipped. Beautiful living area, lots of glass doors that open to a private pool, wrapped by a huge deck …see more

from $459 / night

$3129 / week

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from $459 / night