50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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159 Vacation rentals

(10) Excellent 

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

from $225 / night

$1500 - $3900 / week

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from $225 / night

(2) Excellent 

12

Vacation apartment in Simpson Bay Beach

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 $118 / night

$825 / week

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from $118 / night

34

Villa accommodation 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
Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom V …see more

from $786 / night

$5502 / week

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from $786 / night

(27) Excellent 

12

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 2015 & 2016 and Rated Best Vacation rental in St. Maarten for 2012 - 2014, 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 prope …see more

from $99 / night

$693 - $1393 / week

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from $99 / night

30

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
Memorial weekend special: Every 5th night for free!Book between May 22 - 29, 2017. Minimum 5 nights and travel between May 26 - December 14 2017 Father's Day... Book between June 12 - 19 2017. Receive an additional 10% discount on the best available rate! Minimum 7 nigh …see more

from $265 / night

$1850 - $4000 / week

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from $265 / 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 $258 / night

$1800 - $3600 / week

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from $258 / 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 $414 / night

$2900 - $5900 / week

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from $414 / night

(2) Very Good 

32

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
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

$1008 / week

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from $144 / 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

$1500 / week

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from $214 / night

23

Vacation villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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

$6000 - $9400 / week

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from $857 / night

(2) Very Good 

34

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
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 $543 / night

$3801 - $7504 / week

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from $543 / night

13

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
Located right on the beach in prestigious Pelican Key area on the Dutch side of St. Maarten lays IL Punto Blu. Convenience, spaciousness and panoramic views are the distinct advantages along with outstanding amenities at IL Punto Blu. Does the thought of crowded h …see more

from $336 / night

$2352 - $4004 / week

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from $336 / night

(1) Excellent 

15

Vacation apartment in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $250 / night

$1750 / week

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from $250 / night

(7) Excellent 

22

Vacation villa accommodation

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in a private gated community, perched along the ocean cliffs in Pelican Key (just above Simpson Bay) St Maarten, stands Villa Velaire - a private two bedroom/2.5 bath rental villa. The Villa, recently renovated and completely redecorated in September of 2013, us …see more

from $207 / night

$1450 - $3352 / week

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from $207 / night

(1) Excellent 

15

Vacation apartment rental

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • 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

$2900 - $5900 / week

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from $415 / 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 $450 / night

$3150 - $8890 / week

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from $450 / night

14

Condo rental in Simpson Bay

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
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

$1050 / week

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from $150 / night

22

Vacation villa with swimming 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

$4000 - $9000 / week

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from $572 / 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

$2495 / week

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from $350 / 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
Villa Provence enjoys a majestic view from its elevated location up on the Pelican Key and offers breathtaking sunsets every evening. Imagine watching the sun set with a delicious local cocktail in hand while in your private pool or under the shaded wraparound veranda.. …see more

from $572 / night

$4000 - $9700 / week

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from $572 / 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 $258 / night

$1800 - $3500 / week

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from $258 / night

(3) Very Good 

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 $285 / night

$1995 - $5850 / week

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from $285 / night

24

Vacation home in Simpson Bay

Sint Maarten / Simpson Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Welcome to a wonderfully relaxing and romantic hideaway, CARISMA on the BEACH at Pelican Key... Charming yet classy; sophisticated yet very comfortable, it is perfect for couples and families! This newly renovated 2 bedroom, 2 bath villa has everything to make your vaca …see more

from $258 / night

$1800 - $3800 / week

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from $258 / 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 $258 / night

$1800 - $3600 / week

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from $258 / 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
Looking for that one of a kind romantic hideaway on a fabulous beach without the huge price tag? You’ve found it! The Guest Cottage of Colony Manor Goldendaze sits directly on Sint Maarten’s beautiful soft white sandy beach, Simpson Bay. This luxurious, and oh so charmi …see more

from $200 / night

$1400 - $2500 / week

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from $200 / night

9

Vacation b&b in Simpson Bay

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Air conditioning
Bed and Breakfast 3 rooms in a Luxury Villa "Le Privé" Spa, relaxation, Health House Terrace Sea caribbean and private pool 5 minutes walk from the Sea  A Pelican Key the best place to do skorling. Lunch is free house, gluten free, juice squeezed health, tea tasting W …see more

from $125 / night

$875 / week

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from $125 / night

33

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $543 / night

$3800 - $7500 / week

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from $543 / night

21

Villa rental in Simpson Bay with swimming 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

$2500 - $5000 / week

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from $358 / night

10

Vacation apartment in Simpson Bay

Sint Maarten / Simpson Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Suitable for children age 5+
Luxury two bedroom penthouse unit at the prestigious Aqualina Beach Club directly on beautiful Simpson Bay beach. Unit 402 is the ideal property for one or two couples that love private outdoor living. This unique property has one of the largest private rooftops on the …see more

from $536 / night

$3750 - $6500 / week

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from $536 / night

(2) Very Good 

23

Home rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
CASA DE BELLA is a very comfortable, fully air-conditioned 3 bedroom, 2 ½ bath townhome with views towards Simpson Bay and the Simpson Bay Lagoon... and it has a private pool! It is conveniently located an easy, short walk to a plethora of shopping, beaches (Kim Shaw is …see more

from $279 / night

$1950 - $4000 / week

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from $279 / night

(1) Very Good 

24

Apartment rental in Simpson Bay with shared pool

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Memorial weekend special: Every 5th night for free!Book between May 22 - 29, 2017. Minimum 5 nights and travel between May 26 - December 14 2017 Father's Day... Book between June 12 - 19 2017. Receive an additional 10% discount on the best available rate! Minimum 7 nigh …see more

from $215 / night

$1500 - $2450 / week

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from $215 / night

34

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2 or 3 Bedro …see more

from $786 / night

$5502 / week

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from $786 / night

(5) Excellent 

17

Vacation apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Nestled on top of Pelican Key on Sint Maarten is Son Risa Penthouse; where spectacular views of of the Caribbean Sea await you. This tropical oasis is set just far enough from the entertainment neighborhood to allow for quiet relaxation while still with in walking dista …see more

from $125 / night

$650 - $2500 / week

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from $125 / night

(3) Excellent 

19

Simpson Bay Vacation apartment rental

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Rates vary depending on # of bedrooms rented. Please see rate table or call for details.Crystal clear turquoise sea flecked with dazzling tropical sun, powdery white sands stretching along one of St Maartens longest beaches; Lush exotic foliage surrounding an elegant bu …see more

from $315 / night

$2205 - $5900 / week

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from $315 / 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

$1750 / week

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from $225 / night

30

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
  • 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

$4600 - $7900 / week

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from $657 / night

19

Vacation apartment accommodation

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Wow! Sur Mer is one of those rare affordable 3 bedrooms, 3 bath condos on a gorgeous white sandy beach! This spacious, well-furnished beachfront condo is located smack dab on Simpson Bay Beach in the lovely gated community of Coco's Beach Club! Walk up a flight of stair …see more

from $343 / night

$2400 - $5400 / week

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from $343 / night

34

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom V …see more

from $700 / night

$4900 / week

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from $700 / 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 $543 / night

$3800 - $7500 / week

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from $543 / night

34

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2 or 3 Bedroom V …see more

from $643 / night

$4501 / week

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from $643 / night

1