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Simpson Bay Rentals

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Simpson Bay Rentals

167 rentals

Faja Lobie at Beacon Hill, Saint Maarten - Beachfront & Pool

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$558

1 / 33

Villa Tara at Beacon Hill, Saint Maarten - Oceanfront & Pool

Simpson Bay villa

5 bedrooms / 6 bathrooms / Sleeps 10

$657

1 / 30

Diamond Chateau at Cole Bay, Saint Maarten - Ocean View, Pool, Private

Simpson Bay villa

5 bedrooms / 6 bathrooms / Sleeps 10

$1,010

1 / 40

Villa Hardman

Simpson Bay villa

5 bedrooms / 5 bathrooms / Sleeps 10

$143

1 / 21

Coco Beach #5 ON THE BEACH

Simpson Bay apartment

2 bedrooms / 5 bathrooms / Sleeps 6

$372

1 / 9

Villa Sapphire - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$358

1 / 14

Sur Mer at Simpson Bay, Saint Maarten - Beachfront Gated Community, Pool

Simpson Bay apartment

3 bedrooms / 3 bathrooms / Sleeps 6

$414

1 / 20

La Casita - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$358

1 / 21

Faja Lobie - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$412

1 / 25

Survived Irma!! Beachfront gated Condo directly on Simpson Bay

Simpson Bay apartment

2 bedrooms / 3 bathrooms / Sleeps 5

“Incredible” My husband and I have been back 5 times already and will be returning again this March with more friends. The condo is located on one of St Maarten's finest beaches. Stroll down the beach to Karakters for an incredible mojito and appetize

$250

1 / 16

Brand New House Indigo Bay beach, St Maarten

Simpson Bay house

3 bedrooms / 2 bathrooms / Sleeps 6

$395

1 / 23

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

1 bedroom / 2 bathrooms / Sleeps 2

$225

1 / 33

Belle Amour - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

5 bedrooms / 4 bathrooms / Sleeps 10

$543

1 / 16

Aqualina Beach Club Unit 102 (This Is A Very Special Residence Known As

Simpson Bay villa

2 bedrooms / 2 bathrooms / Sleeps 4

$415

1 / 16

La Vista Grande at Beacon Hill, Saint Maarten- Ocean View & Pool, Walk to the Be

Simpson Bay villa

3 bedrooms / 2 bathrooms / Sleeps 6

$714

1 / 30

Le Papillon Penthouse - REOPENED AFTER IRMA - roof top jacuzzi with great view

Simpson Bay apartment

3 bedrooms / 4 bathrooms / Sleeps 8

$432

1 / 24

Colony Manor

Simpson Bay house

1 bedroom / 2 bathrooms / Sleeps 2

$314

1 / 11

Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view

Simpson Bay apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$299

1 / 24

Pearl on the Beach

Simpson Bay condo

2 bedrooms / 3 bathrooms / Sleeps 4

$519

1 / 17

Tropical Paradise Villa at Coral Shores in Pelican

Simpson Bay villa

2 bedrooms / 2 bathrooms / Sleeps 4

$234

1 / 22

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

Simpson Bay house

2 bedrooms / 1 bathroom / Sleeps 4

“Fabulous resort living with a tropical breeze!” A most wonderful place to enjoy all St Maarten has to offer! Beautiful, airy, spotless accommodations with a contemporary Carribean decor and all the amenities you need for a wondrous vacation! Centrally

$214

1 / 20

Provence at Pelican Key, Saint Maarten - Ocean View, Pool, Lovely Outdoor Living

Simpson Bay villa

6 bedrooms / 4 bathrooms / Sleeps 12

$643

1 / 39

Coco unit 16 - Luxury ocean front condo

Simpson Bay house

3 bedrooms / 3 bathrooms / Sleeps 6

$342

1 / 21

2 Bedrooms 2 Bathrooms Cliffside Villa - Bay Views

Simpson Bay villa

2 bedrooms / 2 bathrooms / Sleeps 4

$280

1 / 21

Villa La-Di-Da at Pelican Key, Saint Maarten - Spectacular Ocean View, Infinity

Simpson Bay villa

6 bedrooms / 6 bathrooms / Sleeps 12

$857

1 / 23

Coral Breeze - STM

Simpson Bay villa

5 bedrooms / 4 bathrooms / Sleeps 12

$856

1 / 16

1Bedroom in Pelican Key

Simpson Bay apartment

1 bedroom / 1 bathroom / Sleeps 5

$275

1 / 11

Modern Luxury Directly on the Beach

Simpson Bay condo

2 bedrooms / 2 bathrooms / Sleeps 4

$277

1 / 17

Beachfront Condo

Simpson Bay condo

2 bedrooms / 3 bathrooms / Sleeps 4

$519

1 / 9

Simpson Bay Beach Modern Luxury Ocean View 1 BR

Simpson Bay apartment

1 bedroom / 1 bathroom / Sleeps 4

$144

1 / 32

Caribbean Sun

Simpson Bay condo

2 bedrooms / 3 bathrooms / Sleeps 4

$300

1 / 34

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

Simpson Bay apartment

1 bedroom / 1 bathroom / Sleeps 2

$130

1 / 12

Condo Bella

Simpson Bay condo

1 bedroom / 1 bathroom / Sleeps 3

$210

1 / 15

CORAL BREEZE...Large affordable beachfront villa! Bring the whole family!

Simpson Bay house

5 bedrooms / 5 bathrooms / Sleeps 10

$1,051

1 / 15

SAPPHIRE... IRMA Survivor!! A casual, comfortable villa with ocean views in Pel

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$571

1 / 13

Faja Lobie

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

“Out of the way but very convenient” Beautiful home and easy access to all the island. Car rental is a must. But very easy to navigate the island

$558

1 / 30

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

1 bedroom / 1 bathroom / Sleeps 4

$149

1 / 22

Blue Pelican Luxury Villas - Featured on HGTV!!!!!

Simpson Bay apartment

1 bedroom / 1 bathroom / Sleeps 2

“Excellent place to stay.” The pre-trip information was perfect and the welcome "meet and greet" was perfect and thorough too. We stayed in Villa #2. Essentially, you couldn't wish for more on the inside - serious attention has been paid to detail and

$169

1 / 14
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