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Simpson Bay Vacation Rentals

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129 rentals in Simpson Bay.

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Paradise Found at Las Arenas - Beachfront Luxury!, vacation rental in Simpson Bay

Paradise Found at Las Arenas - Beachfront Luxury!

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`, vacation rental in Simpson Bay

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Affordable Luxury~Sea Belle Villa on Simpson Bay St Maarten~Beachfront with Pool, vacation rental in Simpson Bay

Affordable Luxury~Sea Belle Villa on Simpson Bay St Maarten~Beachfront with Pool

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath, vacation rental in Simpson Bay

Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Carisma on the beach, vacation rental in Simpson Bay

Carisma on the beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Blue Pelican Luxury Villas - Featured on HGTV!!!!!, vacation rental in Simpson Bay

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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'BOOKING HIGH SEASON'  WORK & STUDY WITH VIEW OF BEAUTIFUL SUNSETS & CARIBBEAN, vacation rental in Simpson Bay

'BOOKING HIGH SEASON' WORK & STUDY WITH VIEW OF BEAUTIFUL SUNSETS & CARIBBEAN

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beach Front Property Ideal for Large Groups of Friends & Family, vacation rental in Simpson Bay

Beach Front Property Ideal for Large Groups of Friends & Family

5 bedrooms
5 bathrooms
Sleeps 14
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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Introducing 'Le Bleu'...contemporary elegance at its best, vacation rental in Simpson Bay

Introducing 'Le Bleu'...contemporary elegance at its best

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Beachfront, Ground Floor, Affordable...crystal clear water, vacation rental in Simpson Bay

Beachfront, Ground Floor, Affordable...crystal clear water

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beach Front Property In Beacon Hill St. Maarten, vacation rental in Simpson Bay

Beach Front Property In Beacon Hill St. Maarten

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful, New & Beachfront  ....'Island Mermaid', vacation rental in Simpson Bay

Beautiful, New & Beachfront ....'Island Mermaid'

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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TOP OF THE ART PENTHOUSE - luxury on the beach, vacation rental in Simpson Bay

TOP OF THE ART PENTHOUSE - luxury on the beach

3 bedrooms
4 bathrooms
Sleeps 8
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

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

1 bedroom
1 bathroom
Sleeps 2
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

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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fab new 1 bed 1 bath  with extras, vacation rental in Simpson Bay

fab new 1 bed 1 bath with extras

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Le Papillon - Modern Luxurious Beachfront Unit, extra clean, stunning view, vacation rental in Simpson Bay

Le Papillon - Modern Luxurious Beachfront Unit, extra clean, stunning view

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront gated Condo directly on Simpson Bay, vacation rental in Simpson Bay

Beachfront gated Condo directly on Simpson Bay

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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2BR-Oceanfront-Royal Palm, vacation rental in Simpson Bay

2BR-Oceanfront-Royal Palm

2 bedrooms
2 bathrooms
Sleeps 6
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!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly renovated, full Studio Appartment, in Top Location walking distance, vacation rental in Simpson Bay

Newly renovated, full Studio Appartment, in Top Location walking distance

1 bedroom
1 bathroom
Sleeps 2
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

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

Studio on the water in the Simpson Bay Yacht Club

1 bedroom
1 bathroom
Sleeps 2
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!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI, vacation rental in Simpson Bay

Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW, vacation rental in Simpson Bay

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing View Penthouse apartment on Simpson Bay Beach  WE ARE BACK AFTER IRMA, vacation rental in Simpson Bay

Amazing View Penthouse apartment on Simpson Bay Beach WE ARE BACK AFTER IRMA

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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BEACHFRONTBLISS, vacation rental in Simpson Bay

BEACHFRONTBLISS

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2 BEDR townhouse overlooking OCEAN  ST- MAARTEN, vacation rental in Simpson Bay

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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El Zafiro: Pearl Suite - Peace of mind!, vacation rental in Simpson Bay

El Zafiro: Pearl Suite - Peace of mind!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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A2 Condo on the Beach at La Siesta, vacation rental in Simpson Bay

A2 Condo on the Beach at La Siesta

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

2 bedrooms
2 bathrooms
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

6 bedrooms
7 bathrooms
Sleeps 12
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!!

3 bedrooms
2 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

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay  (THE SAND CASTLE), vacation rental in Simpson Bay

BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay (THE SAND CASTLE)

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Popular Beachfront property/ Barefoot in SXM, vacation rental in Simpson Bay

Popular Beachfront property/ Barefoot in SXM

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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LA PLAGE PENTHOUSE....3BR suite in Royal Islander Resort...walk to restaurants,, vacation rental in Simpson Bay

LA PLAGE PENTHOUSE....3BR suite in Royal Islander Resort...walk to restaurants,

3 bedrooms
4 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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spellbound Too Catamaran *Fully-Crewed & All-Inclusive*, vacation rental in Simpson Bay

Spellbound Too Catamaran *Fully-Crewed & All-Inclusive*

3 bedrooms
3 bathrooms
Sleeps 6
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

3 bedrooms
3 bathrooms
Sleeps 6
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!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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El Zafiro: Aquamarine Suite- Breathtaking views!, vacation rental in Simpson Bay

El Zafiro: Aquamarine Suite- Breathtaking views!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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ROYAL PALM BEACH #101 ... 3 BR beachfront resort!  Close to restaurants & shoppi, vacation rental in Simpson Bay

ROYAL PALM BEACH #101 ... 3 BR beachfront resort! Close to restaurants & shoppi

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation Villa at Simpson's bay and Marina, vacation rental in Simpson Bay

Vacation Villa at Simpson's bay and Marina

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1 Bed Luxury Condo, vacation rental in Simpson Bay

1 Bed Luxury Condo

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pelican Key 1Bedroom For Rent, vacation rental in Simpson Bay

Pelican Key 1Bedroom For Rent

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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