50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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3,243 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 $402 / night

$2,810 / week

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from $402 / night

33

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Faja Lobie has become a very popular rental home over the last two years. This beautiful, newly renovated three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side. This home offers a wonderful combinat …see more

from $558 / night

$3,906 - $4,403 / week

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from $558 / night

23

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
Aqualina 102 St Maarten. Families or groups of four often find it difficult to locate luxury accommodations with the same long lists of amenities that larger villa properties offer. However, Villa Aqualina Beach Club Unit 102 has been created with such groups in mind. W …see more

from $314 / night

$2,200 - $5,900 / week

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from $314 / night

21

Villa rental in Simpson Bay

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
La Casita Villa is the perfect destination if you are looking for a romantic getaway or an unforgettable vacation with family or friends. This vacation home is ideal for 2 to 6 people. La Casita is an exceptional 3 bedroom, 3 bathroom private home located on the o …see more

from $358 / night

$2,500 - $3,800 / week

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from $358 / 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, the best experience on Simpson Bay beach. - Gated, private & secure community - 3 floor penthouse - 4560 sq. feet unit - Cleaning service every second day - Roof terrace with long chairs, dining area, summer kitchen and 360 degrees vie …see more

from $429 / night

$2,995 - $8,820 / week

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Responds fast!
avg. 3 hours 37 minutes

from $429 / 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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from $395 / night

(2) Very Good 

30

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
Faja Lobie has become a very popular rental home. This beautiful, three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side of St. Maarten. This home offers a wonderful combination of indoor and outdoor …see more

from $458 / night

$3,206 - $6,748 / week

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Responds fast!
avg. 22 minutes

from $458 / night

23

Vacation villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
La-di-da is a gorgeous, contemporary 4 bedroom, 4 bath villa with a 2 bedroom apartment located below the main part of the villa that sits high atop a hill at the mouth of Pelican Key. This setting provides wonderful privacy at the villa. From the living areas, decks an …see more

from $857 / night

$6,000 - $7,800 / week

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from $857 / night

(1) Excellent 

15

Vacation apartment rental

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Crystal clear turquoise sea flecked with dazzling tropical sun, powdery white sands stretching along one of St. Maarten’s longest beaches; Lush exotic foliage surrounding an elegant building of architectural beauty. All of this belongs to Aqualina, St. Maarten’s n …see more

from $415 / night

$2,900 - $3,900 / week

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from $415 / night

13

Vacation condo with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fully renovated condo in Pelican Key. Walk to beach nite life resturants,casino grocery store Pool in back. Safe and quit area in Pelican key. Local contact to help with any special needs. If needed attached newly renovated studio with Queen bed separate ac ,tv/cab …see more

from $129 / night

$800 / week

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from $129 / night

(4) 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, 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 $299 / night

$2,095 - $5,850 / week

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Responds fast!
avg. 3 hours 37 minutes

from $299 / night

13

Vacation studio in Simpson Bay

Sint Maarten / Simpson Bay

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, JetSki (Personal Watercraft), Security System …see more

from $286 / night

$2,000 - $2,500 / week

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from $286 / night

(14) Excellent 

Certificate of Excellence

22

Vacation villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
An instant feeling of genuine coziness and warmth overcomes you upon entering Charisma. Tucked away she is, in a little maze of precious ocean front properties in the peaceful Pelican Key area. Overlooking the spectacular aquatic azure Caribbean Sea, this friendly two b …see more

Certificate of Excellence

from $230 / night

$1,500 - $2,800 / week

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Responds fast!
avg. 3 hours 2 minutes

from $230 / night

41

Vacation villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
“The Reef “ is a beautiful 5 bedroom contemporary villa, superbly positioned on the Simpson Bay Lagoon on the Dutch side of the island of St. Martin/St. Maarten. The villa has its own private boat dock, an amazing lounging terrace with very private exterior living areas …see more

from $1,143 / night

$8,000 - $12,000 / week

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from $1,143 / night

25

Simpson Bay Vacation villa accommodation

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Faja Lobie has become a very popular rental home over the last two years. This beautiful, newly renovated three bedroom, three bath villa sits directly on Bourgeaux Bay beach in the residential area of Beacon Hill on the Dutch side.  This home offers a wonderful combina …see more

from $412 / night

$2,880 - $3,960 / week

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from $412 / 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

20

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Sur Mer is a beachfront condo, located on Simpson Bay Beach in the Coco Beach complex! This great 3 bedroom – 3 bath beautiful St Maarten condo is the perfect rental for your vacation! Sur Mer has every amenity for a comfortable stay: including central air, satellite TV …see more

from $414 / night

$2,900 - $3,700 / week

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from $414 / night

30

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Built on a cliff, directly above the tropical blue sea. The luxury rental Villa Tara offers vacationers a 'one of a kind' experience. The backyard of this home is the majestic Caribbean Sea, and it can be admired from almost every room in this villa. Cleverly designed p …see more

from $657 / night

$4,600 - $5,900 / week

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from $657 / night

(3) Excellent 

13

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Air conditioning
Spacious Penthouse at La Siesta on the Simpson Bay Beach with truly amazing views. Two Bedrooms with en suite plus a Powder room. Master Bed has Four Poster King Size Bed on Beach side, Second Bed is Queen size both have en suites and each has a safe, with walk in sho …see more

from $300 / night

$2,100 - $2,800 / week

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from $300 / night

2

Apartment rental in Simpson Bay with shared pool

Sint Maarten / Simpson Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Luxury two bedroom unit at the prestigious Aqualina Beach Club directly on beautiful Simpson Bay beach. Unit 101 is the ideal property for one or two couples that love outdoor living and easy access to the beach and the turquoise Caribbean Sea. The unit is one of thre …see more

from $425 / night

$2,900 - $4,250 / week

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from $425 / night

14

Simpson Bay Vacation condo rental

Sint Maarten / Simpson Bay

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Ask about pets
This lovely ocean edge condominium is located in a nice and peaceful neighborhood of Beacon Hill. Within 10 min walking distance from all attractions of the famous MAHO bay: beaches, restaurants, bars, casinos, nightclubs, grocery stores and druggist. Enjoy the sunris …see more

from $200 / night

$1,400 / week

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from $200 / night

16

Vacation villa rental

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
This is a beautiful oceanfront 5 bedroom, 4 bathroom property that is located in a nice quiet area of Beacon Hill overlooking Burgeaux Bay on Dutch, St. Maarten.This villa offers amazing colours in the morning and unique sunsets. The villa is located within walking dist …see more

from $543 / night

$3,800 - $5,800 / week

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from $543 / night

11

Vacation home in Simpson Bay

Sint Maarten / Simpson Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Directly on Sint Maarten’s Simpson Bay beaches, this luxurious studio guest house has everything you need for your vacation. This large studio is fully equipped with a full kitchen including a full size electric stove, microwave, refrigerator, dishwasher and Keurig coff …see more

from $314 / night

$2,200 / week

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from $314 / night

18

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $643 / night

$4,500 / week

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from $643 / 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 - $3,000 / week

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from $342 / night

(29) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $169 / night

$1,183 - $1,393 / week

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Responds fast!
avg. 2 hours 42 minutes

from $169 / 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

25

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $329 / night

$2,300 - $3,500 / week

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from $329 / night

20

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Chairs, Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $386 / night

$2,700 - $3,500 / week

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from $386 / 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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Responds fast!
avg. 2 hours 28 minutes

from $150 / 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

22

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft), Security System …see more

from $372 / night

$2,600 - $3,600 / week

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from $372 / night

(4) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $350 / night

$2,495 / week

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from $350 / 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 $130 / night

$911 / week

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Responds fast!
avg. 3 hours 7 minutes

from $130 / night

15

Vacation condo in Simpson Bay

Sint Maarten / Simpson Bay

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
This lovely ocean edge condominium is located in a nice and peaceful neighborhood of Beacon Hill. Within 10 min walking distance from all attractions of the famous MAHO bay: beaches, restaurants, bars, casinos, nightclubs, grocery stores and druggist. Enjoy the sunris …see more

from $210 / night

$1,470 / week

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from $210 / night

27

Simpson Bay Vacation condo rental

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Air conditioning
Sea Belle Villa at La Siesta Residence is an oceanfront, ground floor, 1 bedroom condo directly on Simpson Bay beach. It is on the Dutch side of St. Maarten/SXM in a quiet residential neighborhood conveniently located to restaurants, grocery stores, bakeries, shopping, …see more

from $179 / night

$1,253 / week

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from $179 / night

16

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
This 2 Bedroom Villa can be rented as a 1 Bedroom Villa at a special rate! This is a very special residence known as Villa 182 located directly on beautiful Simpson Bay Beach! Enjoy one of the best locations where you are virtually surrounded by water views and balmy Ca …see more

from $415 / night

$2,905 / week

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from $415 / 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

14

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

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
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $429 / night

$3,000 - $4,500 / week

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from $429 / night