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Holiday Rentals in Simpson Bay

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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, holiday rental in Simpson Bay
#1 Beach House on the Ocean with Private Pool, HGTV  Villa Incognito, holiday rental in Simpson Bay
#1 Beach House on the Ocean with Private Pool, HGTV  Villa Incognito, holiday rental in Simpson Bay

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath, holiday rental in Simpson Bay
Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath, holiday rental in Simpson Bay
Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath, holiday rental in Simpson Bay

Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV, holiday rental in Simpson Bay
Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV, holiday rental in Simpson Bay
Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV, holiday 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, holiday rental in Simpson Bay
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste, holiday rental in Simpson Bay
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste, holiday rental in Simpson Bay

One Hundred Million Dollar Yacht On Land 5 star Villa Namaste

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO, holiday rental in Simpson Bay
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO, holiday rental in Simpson Bay
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO, holiday 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, holiday rental in Simpson Bay
Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten, holiday rental in Simpson Bay
Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten, holiday 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
More info
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"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL, holiday rental in Simpson Bay
"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL, holiday rental in Simpson Bay
"STUNNING VIEWS OF THE BEAUTIFUL CARIBBEAN" OFFERING SPECIAL DEALS FOR FALL, holiday 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, holiday rental in Simpson Bay
Spectacular ocean view apartment on the beach in the heart of Simpson Bay, holiday rental in Simpson Bay
Spectacular ocean view apartment on the beach in the heart of Simpson Bay, holiday 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., holiday rental in Simpson Bay
Beachfront Ground Floor 2 Bedroom 2 Bath Condo. Completely Renovated Jan. 2021., holiday rental in Simpson Bay
Beachfront Ground Floor 2 Bedroom 2 Bath Condo. Completely Renovated Jan. 2021., holiday 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, holiday rental in Simpson Bay
Beach Front Property Ideal for Large Groups of Friends & Family, holiday rental in Simpson Bay
Beach Front Property Ideal for Large Groups of Friends & Family, holiday rental in Simpson Bay

Beach Front Property Ideal for Large Groups of Friends & Family

Holiday Rental House
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, holiday rental in Simpson Bay
SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY, holiday rental in Simpson Bay
SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY, holiday 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, holiday rental in Simpson Bay
Top of the art penthouse on the beach - 4000 sq. ft of luxury, holiday rental in Simpson Bay
Top of the art penthouse on the beach - 4000 sq. ft of luxury, holiday 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, holiday rental in Simpson Bay
Beachfront, Ground Floor, Affordable...crystal clear water, holiday rental in Simpson Bay
Beachfront, Ground Floor, Affordable...crystal clear water, holiday 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, holiday rental in Simpson Bay
Introducing 'Le Bleu'...contemporary elegance at its best, holiday rental in Simpson Bay
Introducing 'Le Bleu'...contemporary elegance at its best, holiday 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, holiday rental in Simpson Bay
Bella Mare!  Beach Front, Ground Floor & Luxurious, holiday rental in Simpson Bay
Bella Mare!  Beach Front, Ground Floor & Luxurious, holiday rental in Simpson Bay

Bella Mare! Beach Front, Ground Floor & Luxurious

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beach Front Ground Floor Luxury, 2 Bedroom Condo, holiday rental in Simpson Bay
Beach Front Ground Floor Luxury, 2 Bedroom Condo, holiday rental in Simpson Bay
Beach Front Ground Floor Luxury, 2 Bedroom Condo, holiday rental in Simpson Bay

Beach Front Ground Floor Luxury, 2 Bedroom Condo

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

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

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

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

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

Le Papillon on the beach

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub, holiday rental in Simpson Bay
Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub, holiday rental in Simpson Bay
Five Star Luxury Beachfront Condo with Direct Beach Access and Private Hot Tub, holiday 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
More info
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Beach Front Property In Beacon Hill St. Maarten, holiday rental in Simpson Bay
Beach Front Property In Beacon Hill St. Maarten, holiday rental in Simpson Bay
Beach Front Property In Beacon Hill St. Maarten, holiday rental in Simpson Bay

Beach Front Property In Beacon Hill St. Maarten

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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TOP OF THE ART PENTHOUSE, holiday rental in Simpson Bay
TOP OF THE ART PENTHOUSE, holiday rental in Simpson Bay
TOP OF THE ART PENTHOUSE, holiday rental in Simpson Bay

TOP OF THE ART PENTHOUSE

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern and Luxurious ... Directly on the Beach, holiday rental in Simpson Bay
Modern and Luxurious ... Directly on the Beach, holiday rental in Simpson Bay
Modern and Luxurious ... Directly on the Beach, holiday rental in Simpson Bay

Modern and Luxurious ... Directly on the Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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fab 1 bed 1 bath  with extras, holiday rental in Simpson Bay
fab 1 bed 1 bath  with extras, holiday rental in Simpson Bay
fab 1 bed 1 bath  with extras, holiday rental in Simpson Bay

fab 1 bed 1 bath with extras

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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lovely two bed two bath with all amenities, holiday rental in Simpson Bay
lovely two bed two bath with all amenities, holiday rental in Simpson Bay
lovely two bed two bath with all amenities, holiday rental in Simpson Bay

lovely two bed two bath with all amenities

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

Studio Simpson Bay Yacht Club

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

Studio on the water in the Simpson Bay Yacht Club

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Newly renovated, full Studio Appartment, in Top Location walking distance, holiday rental in Simpson Bay
Newly renovated, full Studio Appartment, in Top Location walking distance, holiday rental in Simpson Bay
Newly renovated, full Studio Appartment, in Top Location walking distance, holiday rental in Simpson Bay

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

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

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

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

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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nice , solid  , safe, and fabulous location one bed /one bath, holiday rental in Simpson Bay
nice , solid  , safe, and fabulous location one bed /one bath, holiday rental in Simpson Bay
nice , solid  , safe, and fabulous location one bed /one bath, holiday rental in Simpson Bay

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Apartment on the beach, holiday rental in Simpson Bay
Apartment on the beach, holiday rental in Simpson Bay
Apartment on the beach, holiday rental in Simpson Bay

Apartment on the beach

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

2BR-Oceanfront-Royal Palm

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay 
(THE SANDCASTLE), holiday rental in Simpson Bay
BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay 
(THE SANDCASTLE), holiday rental in Simpson Bay
BEACH FRONT Lovely Spacious 2BR 2.5 Bath Simpson Bay 
(THE SANDCASTLE), holiday 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
More info
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RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!, holiday rental in Simpson Bay
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!, holiday rental in Simpson Bay
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit  on  a great beach!, holiday 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
More info
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UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!, holiday rental in Simpson Bay
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!, holiday rental in Simpson Bay
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!, holiday rental in Simpson Bay

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Apartment in Simpson Bay Yacht Club located on the water, holiday rental in Simpson Bay
Apartment in Simpson Bay Yacht Club located on the water, holiday rental in Simpson Bay
Apartment in Simpson Bay Yacht Club located on the water, holiday rental in Simpson Bay

Apartment in Simpson Bay Yacht Club located on the water

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI , holiday rental in Simpson Bay
Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI , holiday rental in Simpson Bay
Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI , holiday 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
More info
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Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!, holiday rental in Simpson Bay
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!, holiday rental in Simpson Bay
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!, holiday 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
More info
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A2 Condo on the Beach at La Siesta, holiday rental in Simpson Bay
A2 Condo on the Beach at La Siesta, holiday rental in Simpson Bay
A2 Condo on the Beach at La Siesta, holiday rental in Simpson Bay

A2 Condo on the Beach at La Siesta

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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5 Stars luxury on the beach, holiday rental in Simpson Bay
5 Stars luxury on the beach, holiday rental in Simpson Bay
5 Stars luxury on the beach, holiday rental in Simpson Bay

5 Stars luxury on the beach

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

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

Holiday Rental House
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, holiday rental in Simpson Bay
COCO BEACH CLUB 6...walk out onto the sand of  Simpson Bay Beach, holiday rental in Simpson Bay
COCO BEACH CLUB 6...walk out onto the sand of  Simpson Bay Beach, holiday 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
More info
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Villa Jade Pelican Key, holiday rental in Simpson Bay
Villa Jade Pelican Key, holiday rental in Simpson Bay
Villa Jade Pelican Key, holiday rental in Simpson Bay

Villa Jade Pelican Key

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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BEACHFRONTBLISS, holiday rental in Simpson Bay
BEACHFRONTBLISS, holiday rental in Simpson Bay
BEACHFRONTBLISS, holiday 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, holiday rental in Simpson Bay
Beautiful 1-bedroom rental apartment in Simpson Bay, holiday rental in Simpson Bay
Beautiful 1-bedroom rental apartment in Simpson Bay, holiday rental in Simpson Bay

Beautiful 1-bedroom rental apartment in Simpson Bay

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Sapphire: Pearl Suite - Peace of mind!, holiday rental in Simpson Bay
The Sapphire: Pearl Suite - Peace of mind!, holiday rental in Simpson Bay
The Sapphire: Pearl Suite - Peace of mind!, holiday 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., holiday rental in Simpson Bay
The Beach Condo - a modern 2-bedroom beachfront condo packed with amenities., holiday rental in Simpson Bay
The Beach Condo - a modern 2-bedroom beachfront condo packed with amenities., holiday 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
More info
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Stunning ocean front villa, holiday rental in Simpson Bay
Stunning ocean front villa, holiday rental in Simpson Bay
Stunning ocean front villa, holiday rental in Simpson Bay

Stunning ocean front villa

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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COCO BEACH CLUB #5....  Located on the soft white powdery sand of Simpson Bay be, holiday rental in Simpson Bay
COCO BEACH CLUB #5....  Located on the soft white powdery sand of Simpson Bay be, holiday rental in Simpson Bay
COCO BEACH CLUB #5....  Located on the soft white powdery sand of Simpson Bay be, holiday 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
More info
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