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Holiday Rentals in Simpson Bay

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Bedrooms

Bathrooms

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Suitability

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Distinctive Features

Distance from

5 km
216 rentals in Simpson Bay.
Sapphire Ruby Suite - Unforgettable Getaway!, holiday rental in Simpson Bay
Sapphire Ruby Suite - Unforgettable Getaway!, holiday rental in Simpson Bay
Sapphire Ruby Suite - Unforgettable Getaway!, holiday rental in Simpson Bay

Sapphire Ruby Suite - Unforgettable Getaway!

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

The Sapphire: Aquamarine Suite- Breathtaking views!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Studio in Pelican Key Paradise, holiday rental in Simpson Bay
Studio in Pelican Key Paradise, holiday rental in Simpson Bay
Studio in Pelican Key Paradise, holiday 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, holiday rental in Simpson Bay
1 Bed Luxury Condo, holiday rental in Simpson Bay
1 Bed Luxury Condo, holiday rental in Simpson Bay

1 Bed Luxury Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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CARIBBEAN BLUE... 5BR beachfront home in Pelican Key, holiday rental in Simpson Bay
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key, holiday rental in Simpson Bay
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key, holiday rental in Simpson Bay

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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Steps to Caribbean, pool and 2 mile-long beach, holiday rental in Simpson Bay
Steps to Caribbean, pool and 2 mile-long beach, holiday rental in Simpson Bay
Steps to Caribbean, pool and 2 mile-long beach, holiday 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, holiday rental in Simpson Bay
46' Sailing Catamaran - Fully Crewed, All-Inclusive, Vacation Packages, holiday rental in Simpson Bay
46' Sailing Catamaran - Fully Crewed, All-Inclusive, Vacation Packages, holiday rental in Simpson Bay

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Sapphire: Turquoise Suite - Tranquility!, holiday rental in Simpson Bay
The Sapphire: Turquoise Suite - Tranquility!, holiday rental in Simpson Bay
The Sapphire: Turquoise Suite - Tranquility!, holiday 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, holiday rental in Simpson Bay
Ocean Front with Private Pool, holiday rental in Simpson Bay
Ocean Front with Private Pool, holiday rental in Simpson Bay

Ocean Front with Private Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t, holiday rental in Simpson Bay
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t, holiday rental in Simpson Bay
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t, holiday rental in Simpson Bay

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

Holiday Rental House
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!, holiday rental in Simpson Bay
Sleeps 4 ppl. Directly ON beach, no walk necessary; gated w underground parking!, holiday rental in Simpson Bay
Sleeps 4 ppl. Directly ON beach, no walk necessary; gated w underground parking!, holiday 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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1Bedroom in Pelican Key, holiday rental in Simpson Bay
1Bedroom in Pelican Key, holiday rental in Simpson Bay
1Bedroom in Pelican Key, holiday 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!, holiday rental in Simpson Bay
EL Zafiro: Emerald Suite - A Gem within a Gem!, holiday rental in Simpson Bay
EL Zafiro: Emerald Suite - A Gem within a Gem!, holiday 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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Beacon Hill Studio (Simpson Bay), holiday rental in Simpson Bay
Beacon Hill Studio (Simpson Bay), holiday rental in Simpson Bay
Beacon Hill Studio (Simpson Bay), holiday rental in Simpson Bay

Beacon Hill Studio (Simpson Bay)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beach Heaven, holiday rental in Simpson Bay
Beach Heaven, holiday rental in Simpson Bay
Beach Heaven, holiday rental in Simpson Bay

Beach Heaven

Condo/Apartment
2 bedrooms
6 bathrooms
Sleeps 4
Match: Sleeps
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Beach view, holiday rental in Simpson Bay
Beach view, holiday rental in Simpson Bay
Beach view, holiday rental in Simpson Bay

Beach view

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

Modern Luxury Directly on the Beach

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

Popular Beachfront property/ Barefoot in SXM

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

Sapphire Suite - Indulgent retreat!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean, holiday rental in Simpson Bay
Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean, holiday rental in Simpson Bay
Catamaran - Fully-Crewed & All-Inclusive - St. Martin, Caribbean, holiday rental in Simpson Bay

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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White Sands Retreat - Beachside at Beacon Hill, holiday rental in Simpson Bay
White Sands Retreat - Beachside at Beacon Hill, holiday rental in Simpson Bay
White Sands Retreat - Beachside at Beacon Hill, holiday rental in Simpson Bay

White Sands Retreat - Beachside at Beacon Hill

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL", holiday rental in Simpson Bay
"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL", holiday rental in Simpson Bay
"CHRISTMAS STILL AVAILABLE" STUNNING VIEW OF BEAUTIFUL CARIBBEAN "IT'S MAGICAL", holiday 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, 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
2 bedrooms
3 bathrooms
Sleeps 4
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
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Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!, holiday rental in Simpson Bay
Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!, holiday rental in Simpson Bay
Beachfront & Poolfront 2br ground floor directly on Simpson Bay Beach. BLISSFUL!, holiday 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, 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
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VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach., holiday rental in Simpson Bay
VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach., holiday rental in Simpson Bay
VILLA HARMONY HAVEN at AQUA. Brand new condo overlooking Simpson Bay Beach., holiday 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, holiday rental in Simpson Bay
Beachfront villa on Sint Maarten with pool. 3BR, 3 bath. Reduced rates for 2017, holiday rental in Simpson Bay
Beachfront villa on Sint Maarten with pool. 3BR, 3 bath. Reduced rates for 2017, holiday rental in Simpson Bay

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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
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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
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Studio on the water at the Simpson Bay Yacht Club, holiday rental in Simpson Bay
Studio on the water at the Simpson Bay Yacht Club, holiday rental in Simpson Bay
Studio on the water at the Simpson Bay Yacht Club, holiday rental in Simpson Bay

Studio on the water at the Simpson Bay Yacht Club

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sea View * La Siesta, Simpson Bay, St. Maarten, N.A., holiday rental in Simpson Bay
Sea View * La Siesta, Simpson Bay, St. Maarten, N.A., holiday rental in Simpson Bay
Sea View * La Siesta, Simpson Bay, St. Maarten, N.A., holiday 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, 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
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COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!, holiday rental in Simpson Bay
COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!, holiday rental in Simpson Bay
COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!, holiday 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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LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY, holiday rental in Simpson Bay
LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY, holiday rental in Simpson Bay
LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY, holiday rental in Simpson Bay

LUXURIOUS 2 BEDROOM CONDO ON SIMPSON BAY

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Sapphire: Peridot Suite - Iconic Views, holiday rental in Simpson Bay
Sapphire: Peridot Suite - Iconic Views, holiday rental in Simpson Bay
Sapphire: Peridot Suite - Iconic Views, holiday rental in Simpson Bay

Sapphire: Peridot Suite - Iconic Views

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!, holiday rental in Simpson Bay
Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!, holiday rental in Simpson Bay
Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!, holiday rental in Simpson Bay

Ocean View Studio w/ WiFi, Beach Access, Resort Pool & More!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Villa Beach Secrets by Fantasia Villas, holiday rental in Simpson Bay
Villa Beach Secrets by Fantasia Villas, holiday rental in Simpson Bay
Villa Beach Secrets by Fantasia Villas, holiday rental in Simpson Bay

Villa Beach Secrets by Fantasia Villas

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!, holiday rental in Simpson Bay
Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!, holiday rental in Simpson Bay
Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!, holiday rental in Simpson Bay

Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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the beacon, holiday rental in Simpson Bay
the beacon, holiday rental in Simpson Bay
the beacon, holiday rental in Simpson Bay

the beacon

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Encanto - 2 Bedroom Beachfront Condo!, holiday rental in Simpson Bay
Encanto - 2 Bedroom Beachfront Condo!, holiday rental in Simpson Bay
Encanto - 2 Bedroom Beachfront Condo!, holiday rental in Simpson Bay

Encanto - 2 Bedroom Beachfront Condo!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Experience Peace and Comfort in St. Maarten! 2 Spacious Units, Pool, Kitchen!, holiday rental in Simpson Bay
Experience Peace and Comfort in St. Maarten! 2 Spacious Units, Pool, Kitchen!, holiday rental in Simpson Bay
Experience Peace and Comfort in St. Maarten! 2 Spacious Units, Pool, Kitchen!, holiday rental in Simpson Bay

Experience Peace and Comfort in St. Maarten! 2 Spacious Units, Pool, Kitchen!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Sol Y Mar Villa Luxury villa, holiday rental in Simpson Bay
Sol Y Mar Villa Luxury villa, holiday rental in Simpson Bay
Sol Y Mar Villa Luxury villa, holiday rental in Simpson Bay

Sol Y Mar Villa Luxury villa

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
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Relax and Recharge in St. Maarten! Swimming Pool, Full Kitchen, Free Parking!, holiday rental in Simpson Bay
Relax and Recharge in St. Maarten! Swimming Pool, Full Kitchen, Free Parking!, holiday rental in Simpson Bay
Relax and Recharge in St. Maarten! Swimming Pool, Full Kitchen, Free Parking!, holiday rental in Simpson Bay

Relax and Recharge in St. Maarten! Swimming Pool, Full Kitchen, Free Parking!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!, holiday rental in Simpson Bay
Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!, holiday rental in Simpson Bay
Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!, holiday rental in Simpson Bay

Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite, holiday rental in Simpson Bay
Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite, holiday rental in Simpson Bay
Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite, holiday rental in Simpson Bay

Emerald Suite - Cocovaa Beach Resort, Beachfront Private Balcony Suite

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-50 of 216
Frequently Asked Questions about Simpson Bay