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Simpson Bay Rentals

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Simpson Bay Rentals

169 rentals

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

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

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$558

1 / 33

Coco Beach #5 ON THE BEACH

Simpson Bay apartment

2 bedrooms / 5 bathrooms / Sleeps 6

$372

1 / 9

Aqualina 102

Simpson Bay villa

2 bedrooms / 2 bathrooms / Sleeps 4

$414

1 / 23

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

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$571

1 / 13

Riviera - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

3 bedrooms / 4 bathrooms / Sleeps 6

$415

1 / 22

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

Simpson Bay house

5 bedrooms / 5 bathrooms / Sleeps 10

$1,051

1 / 15

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

Simpson Bay apartment

3 bedrooms / 3 bathrooms / Sleeps 6

$414

1 / 20

Summer Hill in Pelican Key, Saint Maarten - Gated, private pool

Simpson Bay villa

5 bedrooms / 4 bathrooms / Sleeps 10

$614

1 / 28

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

1 bedroom / 2 bathrooms / Sleeps 2

$225

1 / 33

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

Simpson Bay villa

5 bedrooms / 6 bathrooms / Sleeps 10

$657

1 / 30

PROVENCE... IRMA Survivor!! Affordable villa, gorgeous views, close to dining,

Simpson Bay villa

6 bedrooms / 6 bathrooms / Sleeps 12

$1,386

1 / 46

BEACHFRONTBLISS

Simpson Bay apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$300

1 / 15

Villa La-Di-Da - Ideal for Couples and Families, Beautiful Pool and Beach

Simpson Bay villa

6 bedrooms / 6 bathrooms / Sleeps 12

$858

1 / 26

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

The Reef at Simpson Bay, Saint Maarten - Private Pool, Ocean Views, Modern

Simpson Bay villa

5 bedrooms / 6 bathrooms / Sleeps 10

$1,143

1 / 41

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

Simpson Bay villa

6 bedrooms / 5 bathrooms / Sleeps 12

$643

1 / 39

WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 7

“Sometimes Things are as awesome as They Seem” Just spent a week at this amazing view and I can't begin to say how great a value you are getting. The view is over 180 degrees...the sunsets are literally in your backyard. There is nothing like spendin

$400

1 / 65

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

Simpson Bay villa

5 bedrooms / 7 bathrooms / Sleeps 10

$1,010

1 / 40

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

Simpson Bay apartment

3 bedrooms / 4 bathrooms / Sleeps 8

$429

1 / 24

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

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

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$714

1 / 30

RENDEZVOUS... IRMA Survivor!! A fabulous 2 BR contemporary 2 BR condo unit on

Simpson Bay apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$643

1 / 14

Simpson Bay Beach Modern Luxury Ocean View 1 BR

Simpson Bay apartment

1 bedroom / 1 bathroom / Sleeps 4

$144

1 / 32

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

Villa Hardman

Simpson Bay villa

5 bedrooms / 5 bathrooms / Sleeps 10

$143

1 / 21

3 bdrm 3 bath Villa on the beach in st. maarten

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 8

$500

1 / 10

Sea Belle Villa ~ Simpson Bay St Maarten ~ Oceanfront with Pool

Simpson Bay condo

1 bedroom / 1 bathroom / Sleeps 2

$179

1 / 27

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

Simpson Bay apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$299

1 / 24

Sea Place Villa ~ Simpson Bay St. Maarten ~ Oceanfront with pool

Simpson Bay condo

2 bedrooms / 2 bathrooms / Sleeps 4

$250

1 / 30

Colony Manor

Simpson Bay house

1 bedroom / 2 bathrooms / Sleeps 2

$314

1 / 11

SMART VILLA...IRMA Survivor, stled beachfront at Pelican Key

Simpson Bay villa

3 bedrooms / 4 bathrooms / Sleeps 6

$429

1 / 29

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

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$412

1 / 25

ST TROPEZ...IRMA Survivor, mazing views of Heineken Regatta from this beautiful

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$729

1 / 16

1Bedroom in Pelican Key

Simpson Bay apartment

1 bedroom / 1 bathroom / Sleeps 5

$275

1 / 11

SIMPSON BAY BEACH CONDO #2...located right on the beach at beautiful Simpson Bay

Simpson Bay apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$371

1 / 22

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

Simpson Bay villa

3 bedrooms / 3 bathrooms / Sleeps 6

$358

1 / 21

CARIBBEAN BLUE... IRMA Survivor 5BR beachfront home in Pelican Key

Simpson Bay villa

5 bedrooms / 5 bathrooms / Sleeps 10

“Best time of our lives!!” Love, Love the house and it's location. Claudette was great and a big help. There is restaurants and stores within walking distance. The house has satellite TV so you get alot of music channels and the sound system is Bose. Y

$1,271

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