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Simpson Bay Vacation Rentals

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200 rentals in Simpson Bay.
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#1 Beach House on the Ocean with Private Pool, HGTV  Villa Incognito, vacation rental in Simpson Bay
#1 Beach House on the Ocean with Private Pool, HGTV  Villa Incognito, vacation rental in Simpson Bay
#1 Beach House on the Ocean with Private Pool, HGTV  Villa Incognito, vacation rental in Simpson Bay

#1 Beach House on the Ocean with Private Pool, HGTV Villa Incognito

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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, vacation rental in Simpson Bay
Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath, vacation rental in Simpson Bay

Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV, vacation rental in Simpson Bay
Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV, vacation rental in Simpson Bay
Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV, vacation rental in Simpson Bay

Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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One Hundred Million Dollar Yacht On Land 5 star Villa Namaste, vacation rental in Simpson Bay
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste, vacation rental in Simpson Bay
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste, vacation rental in Simpson Bay

One Hundred Million Dollar Yacht On Land 5 star Villa Namaste

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO, vacation rental in Simpson Bay
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO, vacation rental in Simpson Bay
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO, vacation rental in Simpson Bay

*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
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
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL, vacation rental in Simpson Bay
"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL, vacation rental in Simpson Bay
"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL, vacation rental in Simpson Bay

"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular ocean view apartment on the beach in the heart of Simpson Bay, vacation rental in Simpson Bay
Spectacular ocean view apartment on the beach in the heart of Simpson Bay, vacation rental in Simpson Bay
Spectacular ocean view apartment on the beach in the heart of Simpson Bay, vacation rental in Simpson Bay

Spectacular ocean view apartment on the beach in the heart of Simpson Bay

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beachfront Ground Floor 2 Bedroom 2 Bath Condo. Completely Renovated Jan. 2021., vacation rental in Simpson Bay
Beachfront Ground Floor 2 Bedroom 2 Bath Condo. Completely Renovated Jan. 2021., vacation rental in Simpson Bay
Beachfront Ground Floor 2 Bedroom 2 Bath Condo. Completely Renovated Jan. 2021., vacation rental in Simpson Bay

Beachfront Ground Floor 2 Bedroom 2 Bath Condo. Completely Renovated Jan. 2021.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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, vacation rental in Simpson Bay
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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY, vacation rental in Simpson Bay
SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY, vacation rental in Simpson Bay
SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY, vacation rental in Simpson Bay

SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Top of the art penthouse on the beach - 4000 sq. ft of luxury, vacation rental in Simpson Bay
Top of the art penthouse on the beach - 4000 sq. ft of luxury, vacation rental in Simpson Bay
Top of the art penthouse on the beach - 4000 sq. ft of luxury, vacation rental in Simpson Bay

Top of the art penthouse on the beach - 4000 sq. ft of luxury

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
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, vacation rental in Simpson Bay
Beachfront, Ground Floor, Affordable...crystal clear water, vacation rental in Simpson Bay

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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, vacation rental in Simpson Bay
Introducing 'Le Bleu'...contemporary elegance at its best, vacation rental in Simpson Bay

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

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Bella Mare!  Beach Front, Ground Floor & Luxurious, vacation rental in Simpson Bay
Bella Mare!  Beach Front, Ground Floor & Luxurious, vacation rental in Simpson Bay
Bella Mare!  Beach Front, Ground Floor & Luxurious, vacation rental in Simpson Bay

Bella Mare! Beach Front, Ground Floor & Luxurious

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beach Front Ground Floor Luxury, 2 Bedroom Condo, vacation rental in Simpson Bay
Beach Front Ground Floor Luxury, 2 Bedroom Condo, vacation rental in Simpson Bay
Beach Front Ground Floor Luxury, 2 Bedroom Condo, vacation rental in Simpson Bay

Beach Front Ground Floor Luxury, 2 Bedroom Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Perfect beach front location� 2 bedroom+ Loft, 2.5 Baths., vacation rental in Simpson Bay
Perfect beach front location� 2 bedroom+ Loft, 2.5 Baths., vacation rental in Simpson Bay
Perfect beach front location� 2 bedroom+ Loft, 2.5 Baths., vacation rental in Simpson Bay

Perfect beach front location� 2 bedroom+ Loft, 2.5 Baths.

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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UNBRIDLED:  Beachfront & Elegance in Simpson Beach's Newest Complex, vacation rental in Simpson Bay
UNBRIDLED:  Beachfront & Elegance in Simpson Beach's Newest Complex, vacation rental in Simpson Bay
UNBRIDLED:  Beachfront & Elegance in Simpson Beach's Newest Complex, vacation rental in Simpson Bay

UNBRIDLED: Beachfront & Elegance in Simpson Beach's Newest Complex

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Le Papillon on the beach, vacation rental in Simpson Bay
Le Papillon on the beach, vacation rental in Simpson Bay
Le Papillon on the beach, vacation rental in Simpson Bay

Le Papillon on the beach

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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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Beach Front Property In Beacon Hill St. Maarten, vacation rental in Simpson Bay
Beach Front Property In Beacon Hill St. Maarten, vacation rental in Simpson Bay
Beach Front Property In Beacon Hill St. Maarten, vacation rental in Simpson Bay

Beach Front Property In Beacon Hill St. Maarten

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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TOP OF THE ART PENTHOUSE, vacation rental in Simpson Bay
TOP OF THE ART PENTHOUSE, vacation rental in Simpson Bay
TOP OF THE ART PENTHOUSE, vacation rental in Simpson Bay

TOP OF THE ART PENTHOUSE

Condo/Apartment
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, 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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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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lovely two bed two bath with all amenities, vacation rental in Simpson Bay
lovely two bed two bath with all amenities, vacation rental in Simpson Bay
lovely two bed two bath with all amenities, vacation rental in Simpson Bay

lovely two bed two bath with all amenities

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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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, vacation rental in Simpson Bay
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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, vacation rental in Simpson Bay
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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*NEW LISTING* *OCEAN EDGE* - DIRECT OCEANFRONT - Luxury & Modern Style, vacation rental in Simpson Bay
*NEW LISTING* *OCEAN EDGE* - DIRECT OCEANFRONT - Luxury & Modern Style, vacation rental in Simpson Bay
*NEW LISTING* *OCEAN EDGE* - DIRECT OCEANFRONT - Luxury & Modern Style, vacation rental in Simpson Bay

*NEW LISTING* *OCEAN EDGE* - DIRECT OCEANFRONT - Luxury & Modern Style

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Simpson Bay Top-Level Oceanfront Penthouse with Private Pool and Ocean Views!, vacation rental in Simpson Bay
Simpson Bay Top-Level Oceanfront Penthouse with Private Pool and Ocean Views!, vacation rental in Simpson Bay
Simpson Bay Top-Level Oceanfront Penthouse with Private Pool and Ocean Views!, vacation rental in Simpson Bay

Simpson Bay Top-Level Oceanfront Penthouse with Private Pool and Ocean Views!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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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Apartment on the beach, vacation rental in Simpson Bay
Apartment on the beach, vacation rental in Simpson Bay
Apartment on the beach, vacation rental in Simpson Bay

Apartment on the beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2BR-Oceanfront-Royal Palm, vacation rental in Simpson Bay
2BR-Oceanfront-Royal Palm, vacation rental in Simpson Bay
2BR-Oceanfront-Royal Palm, vacation rental in Simpson Bay

2BR-Oceanfront-Royal Palm

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay 
(THE SANDCASTLE), vacation rental in Simpson Bay
BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay 
(THE SANDCASTLE), vacation rental in Simpson Bay
BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay 
(THE SANDCASTLE), vacation rental in Simpson Bay

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

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 5
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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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
2 bathrooms
Sleeps 4
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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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 , vacation rental in Simpson Bay
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!, vacation rental in Simpson Bay
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!, vacation rental in Simpson Bay
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!, vacation rental in Simpson Bay

Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
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, vacation rental in Simpson Bay
A2 Condo on the Beach at La Siesta, vacation rental in Simpson Bay

A2 Condo on the Beach at La Siesta

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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5 Stars luxury on the beach, vacation rental in Simpson Bay
5 Stars luxury on the beach, vacation rental in Simpson Bay
5 Stars luxury on the beach, vacation rental in Simpson Bay

5 Stars luxury on the beach

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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BELLA VITA...  Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons, vacation rental in Simpson Bay
BELLA VITA...  Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons, vacation rental in Simpson Bay
BELLA VITA...  Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons, vacation rental in Simpson Bay

BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons

Rental Home
7 bedrooms
8 bathrooms
Sleeps 14
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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Villa Jade Pelican Key, vacation rental in Simpson Bay
Villa Jade Pelican Key, vacation rental in Simpson Bay
Villa Jade Pelican Key, vacation rental in Simpson Bay

Villa Jade Pelican Key

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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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Beautiful 1-bedroom rental apartment in Simpson Bay, vacation rental in Simpson Bay
Beautiful 1-bedroom rental apartment in Simpson Bay, vacation rental in Simpson Bay
Beautiful 1-bedroom rental apartment in Simpson Bay, vacation rental in Simpson Bay

Beautiful 1-bedroom rental apartment in Simpson Bay

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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 Beach Condo - a modern 2-bedroom beachfront condo packed with amenities., vacation rental in Simpson Bay
The Beach Condo - a modern 2-bedroom beachfront condo packed with amenities., vacation rental in Simpson Bay
The Beach Condo - a modern 2-bedroom beachfront condo packed with amenities., vacation rental in Simpson Bay

The Beach Condo - a modern 2-bedroom beachfront condo packed with amenities.

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stunning ocean front villa, vacation rental in Simpson Bay
Stunning ocean front villa, vacation rental in Simpson Bay
Stunning ocean front villa, vacation rental in Simpson Bay

Stunning ocean front villa

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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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