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Simpson Bay Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
239 rentals in Simpson Bay.
Sapphire Ruby Suite - Unforgettable Getaway!, vacation rental in Simpson Bay
Sapphire Ruby Suite - Unforgettable Getaway!, vacation rental in Simpson Bay
Sapphire Ruby Suite - Unforgettable Getaway!, vacation rental in Simpson Bay

Sapphire Ruby Suite - Unforgettable Getaway!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BEACHFRONTBLISS, vacation rental in Simpson Bay
BEACHFRONTBLISS, vacation rental in Simpson Bay
BEACHFRONTBLISS, vacation rental in Simpson Bay

BEACHFRONTBLISS

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Sapphire: Pearl Suite - Peace of mind!, vacation rental in Simpson Bay
The Sapphire: Pearl Suite - Peace of mind!, vacation rental in Simpson Bay
The Sapphire: Pearl Suite - Peace of mind!, vacation rental in Simpson Bay

The Sapphire: Pearl Suite - Peace of mind!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Sapphire: Aquamarine Suite- Breathtaking views!, vacation rental in Simpson Bay
The Sapphire: Aquamarine Suite- Breathtaking views!, vacation rental in Simpson Bay
The Sapphire: Aquamarine Suite- Breathtaking views!, vacation rental in Simpson Bay

The Sapphire: Aquamarine Suite- Breathtaking views!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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TARA... Affordable oceanfront villa, walk to beach, vacation rental in Simpson Bay
TARA... Affordable oceanfront villa, walk to beach, vacation rental in Simpson Bay
TARA... Affordable oceanfront villa, walk to beach, vacation rental in Simpson Bay

TARA... Affordable oceanfront villa, walk to beach

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Studio in Pelican Key Paradise, vacation rental in Simpson Bay
Studio in Pelican Key Paradise, vacation rental in Simpson Bay
Studio in Pelican Key Paradise, vacation rental in Simpson Bay

Studio in Pelican Key Paradise

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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1 Bed Luxury Condo, vacation rental in Simpson Bay
1 Bed Luxury Condo, vacation rental in Simpson Bay
1 Bed Luxury Condo, vacation rental in Simpson Bay

1 Bed Luxury Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COCO BEACH CLUB #5....  Located on the soft white powdery sand of Simpson Bay be, vacation rental in Simpson Bay
COCO BEACH CLUB #5....  Located on the soft white powdery sand of Simpson Bay be, vacation rental in Simpson Bay
COCO BEACH CLUB #5....  Located on the soft white powdery sand of Simpson Bay be, vacation rental in Simpson Bay

COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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CARIBBEAN BLUE... 5BR beachfront home in Pelican Key, vacation rental in Simpson Bay
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key, vacation rental in Simpson Bay
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key, vacation rental in Simpson Bay

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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Steps to Caribbean, pool and 2 mile-long beach, vacation rental in Simpson Bay
Steps to Caribbean, pool and 2 mile-long beach, vacation rental in Simpson Bay
Steps to Caribbean, pool and 2 mile-long beach, vacation rental in Simpson Bay

Steps to Caribbean, pool and 2 mile-long beach

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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46' Sailing Catamaran - Fully Crewed, All-Inclusive, Vacation Packages, vacation rental in Simpson Bay
46' Sailing Catamaran - Fully Crewed, All-Inclusive, Vacation Packages, vacation rental in Simpson Bay
46' Sailing Catamaran - Fully Crewed, All-Inclusive, Vacation Packages, vacation rental in Simpson Bay

46' Sailing Catamaran - Fully Crewed, All-Inclusive, Vacation Packages

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Sapphire: Turquoise Suite - Tranquility!, vacation rental in Simpson Bay
The Sapphire: Turquoise Suite - Tranquility!, vacation rental in Simpson Bay
The Sapphire: Turquoise Suite - Tranquility!, vacation rental in Simpson Bay

The Sapphire: Turquoise Suite - Tranquility!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean Front with Private Pool, vacation rental in Simpson Bay
Ocean Front with Private Pool, vacation rental in Simpson Bay
Ocean Front with Private Pool, vacation rental in Simpson Bay

Ocean Front with Private Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key, vacation rental in Simpson Bay
BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key, vacation rental in Simpson Bay
BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key, vacation rental in Simpson Bay

BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t, vacation rental in Simpson Bay
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t, vacation rental in Simpson Bay
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t, vacation rental in Simpson Bay

SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sleeps 4 ppl. Directly ON beach, no walk necessary; gated w underground parking!, vacation rental in Simpson Bay
Sleeps 4 ppl. Directly ON beach, no walk necessary; gated w underground parking!, vacation rental in Simpson Bay
Sleeps 4 ppl. Directly ON beach, no walk necessary; gated w underground parking!, vacation rental in Simpson Bay

Sleeps 4 ppl. Directly ON beach, no walk necessary; gated w underground parking!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate, vacation rental in Simpson Bay
MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate, vacation rental in Simpson Bay
MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate, vacation rental in Simpson Bay

MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1Bedroom in Pelican Key, vacation rental in Simpson Bay
1Bedroom in Pelican Key, vacation rental in Simpson Bay
1Bedroom in Pelican Key, vacation rental in Simpson Bay

1Bedroom in Pelican Key

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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EL Zafiro: Emerald Suite - A Gem within a Gem!, vacation rental in Simpson Bay
EL Zafiro: Emerald Suite - A Gem within a Gem!, vacation rental in Simpson Bay
EL Zafiro: Emerald Suite - A Gem within a Gem!, vacation rental in Simpson Bay

EL Zafiro: Emerald Suite - A Gem within a Gem!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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WITENBLAUW... Magical Beach Front Estate on Pelican Key, vacation rental in Simpson Bay
WITENBLAUW... Magical Beach Front Estate on Pelican Key, vacation rental in Simpson Bay
WITENBLAUW... Magical Beach Front Estate on Pelican Key, vacation rental in Simpson Bay

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Rental Home
6 bedrooms
7 bathrooms
Sleeps 17
Match: Sleeps
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Beacon Hill Studio (Simpson Bay), vacation rental in Simpson Bay
Beacon Hill Studio (Simpson Bay), vacation rental in Simpson Bay
Beacon Hill Studio (Simpson Bay), vacation rental in Simpson Bay

Beacon Hill Studio (Simpson Bay)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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CASA DE BELLA... Great location at a great price!!, vacation rental in Simpson Bay
CASA DE BELLA... Great location at a great price!!, vacation rental in Simpson Bay
CASA DE BELLA... Great location at a great price!!, vacation rental in Simpson Bay

CASA DE BELLA... Great location at a great price!!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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COCO BEACH CLUB 6...walk out onto the sand of  Simpson Bay Beach, vacation rental in Simpson Bay
COCO BEACH CLUB 6...walk out onto the sand of  Simpson Bay Beach, vacation rental in Simpson Bay
COCO BEACH CLUB 6...walk out onto the sand of  Simpson Bay Beach, vacation rental in Simpson Bay

COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!, vacation rental in Simpson Bay
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!, vacation rental in Simpson Bay
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!, vacation rental in Simpson Bay

RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos, vacation rental in Simpson Bay
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos, vacation rental in Simpson Bay
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos, vacation rental in Simpson Bay

PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beach Heaven, vacation rental in Simpson Bay
Beach Heaven, vacation rental in Simpson Bay
Beach Heaven, vacation rental in Simpson Bay

Beach Heaven

Condo/Apartment
2 bedrooms
6 bathrooms
Sleeps 4
Match: Sleeps
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IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key, vacation rental in Simpson Bay
IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key, vacation rental in Simpson Bay
IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key, vacation rental in Simpson Bay

IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beach view, vacation rental in Simpson Bay
Beach view, vacation rental in Simpson Bay
Beach view, vacation rental in Simpson Bay

Beach view

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Luxury Directly on the Beach, vacation rental in Simpson Bay
Modern Luxury Directly on the Beach, vacation rental in Simpson Bay
Modern Luxury Directly on the Beach, vacation rental in Simpson Bay

Modern Luxury Directly on the Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Popular Beachfront property/ Barefoot in SXM, vacation rental in Simpson Bay
Popular Beachfront property/ Barefoot in SXM, vacation rental in Simpson Bay
Popular Beachfront property/ Barefoot in SXM, vacation rental in Simpson Bay

Popular Beachfront property/ Barefoot in SXM

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sapphire Suite - Indulgent retreat!, vacation rental in Simpson Bay
Sapphire Suite - Indulgent retreat!, vacation rental in Simpson Bay
Sapphire Suite - Indulgent retreat!, vacation rental in Simpson Bay

Sapphire Suite - Indulgent retreat!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!, vacation rental in Simpson Bay
ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!, vacation rental in Simpson Bay
ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!, vacation rental in Simpson Bay

ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!, vacation rental in Simpson Bay
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!, vacation rental in Simpson Bay
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!, vacation rental in Simpson Bay

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean, vacation rental in Simpson Bay
Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean, vacation rental in Simpson Bay
Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean, vacation rental in Simpson Bay

Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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COLONY MANOR GUEST COTTAGE II... Romantic hideaway right on Simpson Bay Beach!, vacation rental in Simpson Bay
COLONY MANOR GUEST COTTAGE II... Romantic hideaway right on Simpson Bay Beach!, vacation rental in Simpson Bay
COLONY MANOR GUEST COTTAGE II... Romantic hideaway right on Simpson Bay Beach!, vacation rental in Simpson Bay

COLONY MANOR GUEST COTTAGE II... Romantic hideaway right on Simpson Bay Beach!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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White Sands Retreat - Beachside at Beacon Hill, vacation rental in Simpson Bay
White Sands Retreat - Beachside at Beacon Hill, vacation rental in Simpson Bay
White Sands Retreat - Beachside at Beacon Hill, vacation rental in Simpson Bay

White Sands Retreat - Beachside at Beacon Hill

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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fab 1 bed 1 bath  with extras, vacation rental in Simpson Bay
fab 1 bed 1 bath  with extras, vacation rental in Simpson Bay
fab 1 bed 1 bath  with extras, vacation rental in Simpson Bay

fab 1 bed 1 bath with extras

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL", vacation rental in Simpson Bay
"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL", vacation rental in Simpson Bay
"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL", vacation rental in Simpson Bay

"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL"

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten, vacation rental in Simpson Bay
Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten, vacation rental in Simpson Bay
Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten, vacation rental in Simpson Bay

Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub, vacation rental in Simpson Bay
Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub, vacation rental in Simpson Bay
Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub, vacation rental in Simpson Bay

Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!, vacation rental in Simpson Bay
Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!, vacation rental in Simpson Bay
Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!, vacation rental in Simpson Bay

Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern and Luxurious ... Directly on the Beach, vacation rental in Simpson Bay
Modern and Luxurious ... Directly on the Beach, vacation rental in Simpson Bay
Modern and Luxurious ... Directly on the Beach, vacation rental in Simpson Bay

Modern and Luxurious ... Directly on the Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach., vacation rental in Simpson Bay
VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach., vacation rental in Simpson Bay
VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach., vacation rental in Simpson Bay

VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach.

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront villa on Sint Maarten with pool. 3BR, 3 bath. Reduced rates for 2017, vacation rental in Simpson Bay
Beachfront villa on Sint Maarten with pool. 3BR, 3 bath. Reduced rates for 2017, vacation rental in Simpson Bay
Beachfront villa on Sint Maarten with pool. 3BR, 3 bath. Reduced rates for 2017, vacation rental in Simpson Bay

Beachfront villa on Sint Maarten with pool. 3BR, 3 bath. Reduced rates for 2017

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Apartment in Simpson Bay Yacht Club located on the water, vacation rental in Simpson Bay
Apartment in Simpson Bay Yacht Club located on the water, vacation rental in Simpson Bay
Apartment in Simpson Bay Yacht Club located on the water, vacation rental in Simpson Bay

Apartment in Simpson Bay Yacht Club located on the water

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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nice , solid  , safe, and fabulous location one bed /one bath, vacation rental in Simpson Bay
nice , solid  , safe, and fabulous location one bed /one bath, vacation rental in Simpson Bay
nice , solid  , safe, and fabulous location one bed /one bath, vacation rental in Simpson Bay

nice , solid , safe, and fabulous location one bed /one bath

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Studio on the water at the Simpson Bay Yacht Club, vacation rental in Simpson Bay
Studio on the water at the Simpson Bay Yacht Club, vacation rental in Simpson Bay
Studio on the water at the Simpson Bay Yacht Club, vacation rental in Simpson Bay

Studio on the water at the Simpson Bay Yacht Club

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sea View * La Siesta, Simpson Bay, St. Maarten, N.A., vacation rental in Simpson Bay
Sea View * La Siesta, Simpson Bay, St. Maarten, N.A., vacation rental in Simpson Bay
Sea View * La Siesta, Simpson Bay, St. Maarten, N.A., vacation rental in Simpson Bay

Sea View * La Siesta, Simpson Bay, St. Maarten, N.A.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Studio Simpson Bay Yacht Club, vacation rental in Simpson Bay
Studio Simpson Bay Yacht Club, vacation rental in Simpson Bay
Studio Simpson Bay Yacht Club, vacation rental in Simpson Bay

Studio Simpson Bay Yacht Club

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!, vacation rental in Simpson Bay
COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!, vacation rental in Simpson Bay
COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!, vacation rental in Simpson Bay

COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Frequently Asked Questions about Simpson Bay