50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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135 Vacation rentals

13

Simpson Bay Vacation apartment accommodation

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $380 / night

$2657 / week

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from $380 / 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 $123 / night

$861 / week

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from $123 / night

46

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. 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 $787 / night

$5503 / week

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from $787 / night

21

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
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 which …see more

from $142 / night

$1000 - $25000 / week

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from $142 / 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 - $3353 / week

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from $207 / night

44

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
  • Child friendly
  • Air conditioning
7th Night Free! Apr 15 - Dec 15, 2017Restrictions Apply!Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.This property may accept holiday stays of less than 14 nights.La-Di-Da is a gorgeous 6 bedroom, 6 bath St. Maarten vacatio …see more

from $500 / night

$3500 - $11901 / week

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from $500 / night

44

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

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

$2200 - $5900 / week

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from $314 / 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

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 $100 / night

$700 / week

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Responds fast!
avg. 1 hour 44 minutes

from $100 / night

(13) 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 $225 / night

$1500 - $2800 / week

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Responds fast!
avg. 3 hours 59 minutes

from $225 / night

14

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

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

(28) 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 $109 / night

$763 - $1393 / week

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Responds fast!
avg. 2 hours 42 minutes

from $109 / 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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Responds fast!
avg. 1 hour 28 minutes

from $450 / night

(1) Excellent 

13

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

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 - $3088 / week

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Responds fast!
avg. 2 hours 41 minutes

from $149 / night

(4) 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

$2200 - $5900 / week

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from $315 / 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
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 offers wonderful views of the Caribbean Sea and Dutch St. Maarten's sp …see more

from $358 / night

$2500 - $6000 / week

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from $358 / 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 $285 / night

$1995 - $5850 / week

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Responds fast!
avg. 1 hour 28 minutes

from $285 / night

(2) Excellent 

14

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
7th Night Free! May 1 - Oct 31, 2017 Maid Service offered 2x p/week when booking the 7th Night Free Promo RatesRates may vary depending on # of bedrooms rented. Please see rate table or call for details.Rendezvous, from the moment you set foot inside the luxurious St. M …see more

from $340 / night

$2380 - $4500 / week

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from $340 / 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

10

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Located over the hill on the sea at Pelican Key, Daffodil is a luxurious,5 bedrooms, 5 bath villa, whose unique glistening cerulean blue tile roof promises a memorable vacation experience. It’s Dutch flavor is showcased by colorful furnishings from international designe …see more

from $1071 / night

$7500 - $10000 / week

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from $1071 / night

16

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
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! Beachside is the best located unit at Palm Beach Condos, a intimate well desig …see more

from $279 / night

$1950 - $4500 / week

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from $279 / night

(2) Excellent 

48

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
A modern tropical retreat in an enclave of privacy offering breathtaking views over the Caribbean sea. Located a few minutes drive away from: - Hollywood Casino - Buccaneer Beach Bar BBQ - Supermarket - French Bakery serving breakfast all day and lunch, Take a stroll …see more

from $515 / night

$3600 - $10000 / week

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from $515 / night

26

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
  • Ask about children
The superbly appointed ‘La Perla Palais” with its three master suites is the principal property in the estate and features exquisitely designed Lulu by YSL interiors. On either side are the one bedroom villas of La Perla Bianca and La Perla Classic each completely indep …see more

Pricing unknown

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Pricing unknown

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 

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

from $300 / night

$2100 / week

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from $300 / night

33

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.VILLA BELLA VITA – Where the amenities of a Five-Star Resort luxury meet with the serenity, the privacy and the personalized service that each guest deserves.Named for the “Beaut …see more

from $1200 / night

$8400 - $25200 / week

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from $1200 / night

22

Simpson Bay Vacation villa rental

Sint Maarten / Simpson Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
Nestled on the beautiful beach of Burgeaux Bay in the area of Beacon Hill in Dutch St. Maarten, Villa Sunshine is a wonderfully spacious 6 bedroom, 6 bathroom home offering beautiful views over the ocean. The villa is constructed on one level providing easy access and m …see more

from $1500 / night

$10500 - $28000 / week

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from $1500 / night

50

Vacation villa in Simpson Bay

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 3 levels, the villa’s immaculate interior spaces include a ground floor, well-equipped and welcoming kitchen, a spacious dining area with a long table easily able to seat 10/12 people and an impressive home cinema with seating for 8. The 2nd floor houses 3 larg …see more

from $1217 / night

$8518 - $19166 / week

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from $1217 / night

41

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
  • 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 $1143 / night

$8000 - $18000 / week

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from $1143 / night

16

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 Free! Apr 15 - Dec 15, 2017Restrictions Apply!St Tropez sits high up on the hill in Pelican Key in Dutch St Maarten and offers outstanding views of the Caribbean Sea and glorious sunsets. This St. Maarten vacation villa for Heineken Regatta participants or fan …see more

from $500 / night

$3500 - $6500 / week

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from $500 / night

23

Vacation villa accommodation

Sint Maarten / Simpson Bay

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Nested on the beautiful Burgeaux Bay beach. Villa Sunset is a wonderful, spacious 5 bedroom 5 bathroom home located in the beacon hill area. This beach front property comes with great amenities such as kayaks and paddle boards that will allow its guest to fully enjoy t …see more

from $700 / night

$4900 / week

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from $700 / 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 $787 / night

$5503 / week

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from $787 / 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

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 - $7901 / week

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from $657 / night

21

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 

13

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
"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 Beach. The disappearing sliding glass doors open to experience "outdoor/ind …see more

from $340 / night

$2380 - $4500 / week

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from $340 / night

28

Vacation villa in Simpson Bay

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Summer Hill is a free standing private villa perched on top of one of the hills of Pelican Key, Dutch St. Maarten. The villa boasts 200 degree views of the turquoise waters of the Caribbean Sea and on a very clear day you can see the neighboring islands of Saba, Statia, …see more

from $614 / night

$4300 - $11000 / week

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from $614 / night