50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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2,472 Vacation rentals

13

Simpson Bay Vacation apartment accommodation

Sint Maarten / Simpson Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful new home was built on the cliff tops Beacon Hill overlooking Simpson Bay and just steps from the beach; The condo has everything from contemporary design to the high quality bedding and a spacious gourmet kitchen we would like to tropical luxury vacation. …see more

from $376 / night

$2,632 / week

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from $376 / night

28

Vacation villa rental

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
You have discovered a place where piercing turquoise waters meet the deeper blue of the sky. The pool and deck area has a private direct access to Cupecoy Beach. This is a small clothing optional beach allowing swimming in the clear blue waters. Bahia Villa is located …see more

from $1,002 / night

$7,014 / week

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from $1,002 / night

(5) Excellent 

24

Apartment rental in Simpson Bay

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, we are the best maintained property on Simpson Bay beach. We recovered well from hurricane Irma and continue to provide the same quality accommodation as we did prior to Irma. THE UNIT INCLUDES: - Gated, private and secure community - 2150 sq. …see more

from $299 / night

$2,095 - $5,850 / week

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Responds fast!
avg. 2 hours 54 minutes

from $299 / night

(1) Excellent 

15

Vacation apartment in Simpson Bay

Sint Maarten / Simpson Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Ask about pets
◾first floor direct access to the pool and beachfront ◾amazing 3 ½ mile crescent of powdery white sand beach with gentle waves ◾private pool front lanai accessible from the master bedroom and living area ◾large, fully functional kitchen, all granite ,new, top grade ap …see more

from $300 / night

$2,100 / week

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from $300 / night

(2) Excellent 

20

Vacation home rental

Sint Maarten / Simpson Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Stylish , furnished 2 bedrooms, townhouse in quiet, residential area in Pelican, Rancho cielo Estates, Bathroom newly renovated with bath and rain shower, large master bedroom with furnished veranda with unobstructed ocean view. Walk-in closet. Very large open plan k …see more

from $214 / night

$1,500 / week

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from $214 / night

21

Vacation home in Simpson Bay

Sint Maarten / Simpson Bay

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Ask about children
Coco Beach Club #16, a true beach front condo, located on the famous Simpson Bay Beach, near Maho and the famous night life that awaits! Imagine waking up in the morning and hearing the waves roll onto the beach from your private patio, then take in a walk right out ont …see more

from $342 / night

$2,400 - $5,400 / week

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from $342 / night

(29) Excellent 

14

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Travelers Choice Award for 2012 - 2017 and Rated Best Vacation rental in St. Maarten for 2017, Blue Pelican Villas is located on the Dutch side of St. Maarten in the exclusive area of Pelican Key. Blue Pelican is a spacious 1 bedroom villa set on an upscale property wit …see more

from $169 / night

$1,183 - $1,393 / week

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Responds fast!
avg. 2 hours 42 minutes

from $169 / night

9

Apartment rental in Simpson Bay with shared pool

Sint Maarten / Simpson Bay

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Coco's Beach #5 is a beautiful location for your vacation or stay in St. Maarten! Located right on the beach in Simpson Bay, you will wake every morning to the sights and sounds of the ocean. Living room and master bedroom have full ocean access with a large outdoor pri …see more

from $372 / night

$2,600 / week

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from $372 / night

(2) Very Good 

32

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Modern 1 bedroom apartment newly built. Marble floors through out. All stainless steel appliances in kitchen and granite counter top. Hi speed WiFi internet. Dish Network Satellite TV in living room and bedroom. Air conditioning in all areas. Very private due it being a …see more

from $144 / night

$1,008 / week

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Responds fast!
avg. 2 hours 33 minutes

from $144 / night

(4) Very Good 

12

Vacation apartment in Simpson Bay Beach

Simpson Bay / Simpson Bay Beach

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • 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 $122 / night

$853 / week

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Responds fast!
avg. 3 hours 59 minutes

from $122 / night

(6) Excellent 

24

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Child friendly
Welcome in Le Papillon Penthouse, we are the best maintained property on Simpson Bay beach. We recovered well from hurricane Irma and continue to provide the same quality accommodation as we did prior to Irma. THE PENTHOUSE INCLUDES: - Gated, private & secure communit …see more

from $429 / night

$2,995 - $8,820 / week

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Responds fast!
avg. 2 hours 54 minutes

from $429 / night

33

Vacation apartment rental

Sint Maarten / Simpson Bay

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
"At Seaside" is our dream...make it yours too! Serene Caribbean views can be enjoyed from the terrace. She is one of 20 units in a gated community surrounding a pool with views of the Caribbean. The grounds are lush and well tended. There is a king-sized bed and master …see more

from $225 / night

$1,750 / week

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from $225 / night

37

Apartment rental in Simpson Bay with shared pool

Sint Maarten / Simpson Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy.Introducing Acqua Azzurra – Brand new, lovely 2 Bedroom, 2.5 Bathroom condo located at the Acqua Residences in Beacon Hill – just steps to the BEACH! Acqua Residences is a new condominium development …see more

from $429 / night

$3,000 - $4,500 / week

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from $429 / night

(16) Excellent 

21

Simpson Bay Vacation home accommodation

Sint Maarten / Simpson Bay

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Rigth next to St Maarten' s Lagoon - A lovely setting, surrounded by trees and plants. Just a short 2 miles hop to the beach, this traditional Caribbean (65m2) villa is ideal for a family. Fully air-conditionned,it has a terrace and a balcony with garden furniture, i …see more

from $89 / night

$623 - $938 / week

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from $89 / night

(1) Excellent 

34

Vacation condo in Simpson Bay

Simpson Bay / Simpson Bay Beach

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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

$2,100 / week

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from $300 / night

22

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Simpson Bay Beach Condo #2 is a beautiful ground floor, well equipped, fully air-conditioned condo located directly on Simpson Bay Beach. Walk off your patio and onto a wonderful soft sandy beach! Enjoy quiet mornings with the birds singing or take an early morning stro …see more

from $515 / night

$3,600 / week

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from $515 / night

(2) Excellent 

22

Simpson Bay Vacation condo rental

Sint Maarten / Simpson Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Watch the sun rise and set from your own private patio or terrace, while enjoying the sunny warm weather and peaceful surrounding of St. Maarten. The contemporary design and facilities will serve your needs and desires during your stay with us. Queen sized bed provides …see more

from $172 / night

$1,204 / week

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from $172 / night

25

Vacation villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The property is located in the very in demand location called Beacon Hill. This property has 5 bedrooms and 5 bathrooms. The villas features huge dining and living room area. The property is fully equipped with wifi , BBQ grill for great outdoor moments. It also has c …see more

from $600 / night

$4,200 / week

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from $600 / night

20

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates oered for less than full occupancy.Wow!! Stunning sunsets will captivate your heart at lovely villa “Belle Amour”... This beautifully rejuvenated, fully air-conditioned 5 bedroom, 4 bathroom oceanfront villa is located in a picturesque, …see more

from $829 / night

$5,800 - $11,500 / week

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from $829 / night

23

Simpson Bay Vacation home rental

Simpson Bay / Simpson Bay Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
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 $395 / night

$2,695 / week

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Responds fast!
avg. 3 hours 58 minutes

from $395 / night

(4) Excellent 

10

Vacation condo with shared pool in Simpson Bay

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

$2,495 / week

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from $350 / 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

$3,605 / week

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from $515 / night

22

Vacation villa with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Villa Provence…from its majestic setting up on the Pelican Key to its breathtaking sunsets every evening with a delicious local cocktail in hand with your private pool on the wraparound veranda., in the sun or in the shade. What a lovely way to spend the days …see more

from $572 / night

$4,000 - $6,000 / week

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from $572 / night

46

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7th Night Free7 night minimumMay 1 - October 31, 2018Please inquire about lower rates offered for less than full occupancy. Villa Provence enjoys a majestic view from its elevated location up on the Pelican Key and offers breathtaking sunsets every evening. Imagine wat …see more

from $1,386 / night

$9,700 / week

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from $1,386 / night

26

Apartment rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Just Blue is a beautiful penthouse on the Simpson Bay Lagoon. This contemporary & modern penthouse has a beautiful view of the Simpson Bay Lagoon and the Caribbean sea. The many yachts moored in the surrounding marinas offer a glittering view, both by day and night. Loc …see more

from $454 / night

$3,180 / week

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from $454 / night

(1) Excellent 

14

Condo rental in Simpson Bay

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Our beautiful 1 bedroom Condo is set high up on Pelican key. It is Quiet secluded and only 5 minutes walk from the beach. Its very modern, clean and luxurious. A perfect quiet secluded hideaway! All amenities are close by, shops, casino and the beach.... not too far fro …see more

from $150 / night

$1,050 / week

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from $150 / night

22

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
Surround yourself with lush tropical gardens and the breathtaking views of the ocean. The large covered terrace overlooks the sparkling oval shaped pool and the beautiful Caribbean Sea. Perfect place for a romantic dinner, cocktails, coffee or just relaxing with a bac …see more

from $234 / night

$1,640 / week

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from $234 / night

(1) Excellent 

14

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
SBBC #3 is a 2 bedroom, 2 bath St. Maarten vacation rental located right on the beach at beautiful Simpson Bay. One of only 12 units in it's development, it offers quiet and comfortable surroundings, and the ocean just footsteps away in Dutch St. Maarten. The condo is l …see more

from $515 / night

$3,600 / week

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from $515 / night

9

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Unique, romantic, comfortable STUDIO in beautiful residential area completely equipped with linens, AC, TV, cable, Wi-Fi, kitchenette, pool, parking right in front. Quiet location with easy access to restaurants, entertainment, beach, casino. water sports, Airpor …see more

from $90 / night

$630 / week

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from $90 / night

14

Vacation villa with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Sapphire, the perfect vacation home, is a charming Caribbean styled house nestled in lush tropical gardens. Sitting high on a hillside in the exclusive Pelican Key area, the house offers wonderful views of the Caribbean Sea and St. Maarten’s spectacular sunsets. …see more

from $358 / night

$2,500 - $3,000 / week

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from $358 / night

39

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This comfortable, relaxing, fully air-conditioned beachfront villa is conveniently located in Beacon Hill within 5 minutes to St Maarten’s bustling Maho, the “nightlife” area of the island, yet is nestled at the quiet end of Burgeoux Bay. Welcome to the peaceful hideawa …see more

from $858 / night

$6,000 - $11,000 / week

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from $858 / night

20

Vacation villa rental

Sint Maarten / Simpson Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Air conditioning
Casa Carib, a new spacious 2 bedroom, 2 bath beachfront Villa of 1700 sq. ft. is located directly on one of the most beautiful (2 1/2 mile ) beaches found anywhere in the Caribbean. Often referred to as the “best kept secret” on the island, Simpson Bay Beach is truly a …see more

from $243 / night

$1,700 / week

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from $243 / night

(1) Excellent 

23

Simpson Bay Vacation condo rental

Sint Maarten / Simpson Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
As with every guest in an El Zafiro suite, you are our VIP, and the Ruby suite will remind you of this every day. A passion for detail in design not only provides the foundation of El Zafiro but is the basis for every experience created and memory made here. The contemp …see more

from $185 / night

$1,295 / week

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from $185 / night

47

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7th Night Free7 night minimumMay 1 - October 31, 2018Please inquire about lower rates offered for less than full occupancy. Built on a cliff, directly above the tropical blue sea, Villa Tara offers vacationers a one of a kind experience. The backyard of this home is the …see more

from $843 / night

$5,900 - $7,900 / week

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from $843 / night

40

Vacation apartment in Simpson Bay

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Construction around property! Please inquire about lower rates offered for less than full occupancy Located right on the beach in prestigious Pelican Key area on the Dutch side of St. Maarten lays Il Punto Blue. Convenience, spaciousness and panoramic views are the dis …see more

from $572 / night

$4,000 / week

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from $572 / night

21

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
This beautiful beachfront 5 bedroom, is located in the quiet area of Beacon Hill overlooking Burgaux Bay. Villa Hardman offers great views in the morning of the grand cruise ships and amazing colors during the sunsets. The villa is within walking distance to Maho whic …see more

from $143 / night

$1,000 - $5,950 / week

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from $143 / night

(1) Excellent 

11

Vacation apartment rental

Sint Maarten / Simpson Bay

2 3 nights min

  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Newly renovated studio features a kitchenette with full fridge, 4 burner glass stove top, microwave, toaster oven, and coffee maker. King size, very comfy bed, flat screen cable tv, and sofa, bathroom with multi jets including rain shower head, and a balcony with seatin …see more

from $150 / night

$1,395 / week

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from $150 / night

28

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Child friendly
Wow!! Stunning sunsets will captivate your heart at lovely villa “Belle Amour”... This beautifully rejuvenated, fully air-conditioned 5 bedroom, 4 bathroom oceanfront villa is located in a picturesque, quiet area of Beacon Hill overlooking the shores of Burgeoux Bay on …see more

from $720 / night

$5,040 / week

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from $720 / night

13

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7th Night Free7 night minimumMay 1 - October 31, 2018Please inquire about lower rates offered for less than full occupancy.Sapphire villa, the perfect St. Maarten vacation rental, is a charming Caribbean styled house nestled in lush tropical gardens. Sitting high on a h …see more

from $572 / night

$4,000 - $6,000 / week

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from $572 / night

(1) Excellent 

9

Vacation hotel apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
This 1 bedroom/1bath unit is located in Pelican Key/Simpson Bay' next to LaVista Resort. Within walking distance to many restaurants, bars, grocery store and casino. The unit has a full kitchen with all the comforts of home, a futon sleeper sofa and cot downstairs for …see more

from $225 / night

$1,250 - $1,945 / week

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from $225 / night