50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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2,608 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 $398 / night

$2,786 / week

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from $398 / 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

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
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 $372 / night

$2,600 - $3,600 / week

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from $372 / 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

(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 $129 / night

$903 / week

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Responds fast!
avg. 3 hours 59 minutes

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, 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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from $299 / 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 43 minutes

from $144 / night

(1) Excellent 

14

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
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 $372 / night

$2,600 - $3,600 / week

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from $372 / night

(1) Excellent 

29

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy.Villa Smart is nestled beachfront at Pelican Key and offers a totally tropical, affordable family St. Maarten vacation rental with direct beach access and glorious ocean views, does not have a swimmin …see more

from $429 / night

$3,000 - $3,600 / week

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from $429 / 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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from $429 / 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

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

21

Villa rental in Simpson Bay with shared pool

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • 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

(15) 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. 2 hours 45 minutes

from $230 / night

25

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Indulge yourself at Maho Dream, a beautiful 2 bedroom Penthouse (4th floor with elevator) locateed in the guard gated community of Blue Marine Residence in Maho, St Martin's fun night life area. This large, fully air-conditioned 2 bedroom , 3 bath condo has all the amm …see more

from $174 / night

$1,215 - $2,450 / week

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from $174 / 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

(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

(2) Excellent 

18

Apartment rental in Simpson Bay

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. 1 hour 49 minutes

from $139 / 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

(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

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

(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

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

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
Please inquire about lower rates offered for less than full occupancy.Practically roll out of bed on to the soft white sand of Simpson Bay beach!! Beachside is a very comfortably furnished 3 bedroom, 3 bath condo located directly on beautiful Simpson Bay beach! Beachs …see more

from $643 / night

$4,500 / week

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from $643 / 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
Marisol is a light and airy St. Maarten vacation rental at Point Blue in Pelican Key Estate. With 2 bedrooms and 3 full bathrooms, this immaculate two storey townhouse provides a quiet and peaceful tropical oasis for your stay in Dutch St. Maarten. Leave the hustle and …see more

from $329 / night

$2,300 - $3,500 / week

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from $329 / night

22

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
Feel like you are transported to the Mediterranean at Villa Riviera. Enjoy this splendid villa, located high on the hillside at Pelican Key, with an unobstructed view of the Caribbean Sea from every room.  Each room opens to the enormous patio which runs the entir …see more

from $415 / night

$2,900 - $3,800 / week

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from $415 / night

10

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Beautiful, Newly remodeled 3 Bedroom, 3 Bath Villa. Breath Taking Views of of the Ocean with an entrance right to the Beach. Very Spacious,with an open floor plan, great for Family and Entertaining groups. Romantic Patio with Jacuzzi and Views of the Sunset Also Make …see more

from $500 / night

$3,200 / week

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Responds fast!
avg. 3 hours 48 minutes

from $500 / 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

25

Simpson Bay Vacation villa accommodation

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 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

(1) Excellent 

23

Simpson Bay Vacation condo rental

Sint Maarten / Simpson Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • 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 $139 / night

$924 - $2,223 / week

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from $139 / 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

(2) Good 

29

Vacation apartment in Simpson Bay

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Atlantis at Coco Beach Club is a great location for your vacation! Located right on the beach at Simpson Bay, you will wake every morning to the sound of the ocean. Atlantis at Coco Beach Club is a one bedroom St. Maarten rental condo, one bathroom unit nicely decorated …see more

from $286 / night

$2,000 - $2,600 / week

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from $286 / 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
Please 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 hillside in the exclusive Pelican Key area. The villa …see more

from $572 / night

$4,000 - $6,000 / week

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from $572 / night

30

Simpson Bay Vacation condo rental

Sint Maarten / Simpson Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Sea Place Villa at La Siesta Residence is an oceanfront, 2nd floor, 2 bedroom condo (both with king beds and ensuites) located directly on Simpson Bay beach with an oceanfront pool. Sea Place is on the Dutch side of St. Maarten/SXM in a quiet residential neighborhood c …see more

from $250 / night

$1,750 / week

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from $250 / night

(3) Very Good 

13

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy. "Unforgettable" is two bedroom, two and a half bathroom ground floor luxury St. Maarten vacation rental condo... is located in Las Arenas, a new contemporary, high quality complex on Simpson Bay Beac …see more

from $519 / night

$3,630 - $4,500 / week

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from $519 / night

(1) Excellent 

22

Vacation condo in Simpson Bay

Sint Maarten / Simpson Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
El Zafiro will lay world class luxury at your feet, your choice of a suite guarantees you an unforgettable experience the moment you walk through the gates. The lavish interior and beautiful sandy beach will transport you to another world and melt away your cares and st …see more

from $149 / night

$991 - $2,289 / week

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from $149 / 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

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

(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