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Holiday Rentals with Pools in Simpson Bay

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53 rentals in Simpson Bay.
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ANCHOR HOUSE - DIRECT OCEANFRONT - Luxury & Modern Style
Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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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, All pools
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Villa Carisma, Fabulous Beachfront, 2 Bedroom, 2 Bath
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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SPECTACULAR 2 BEDROOMS, 2 1/2 BATHROOMS BEACH FRONT UNIT ON SIMPSON BAY
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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*NEW LISTING* *OCEAN EDGE* - DIRECT OCEANFRONT - Luxury & Modern Style
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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2BR-Oceanfront-Royal Palm
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons
Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Save time - get the best Simpson Bay rentals sent straight to your email!
Beautiful 1-bedroom rental apartment in Simpson Bay
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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CASA DE BELLA... Great location at a great price!!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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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, All pools
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CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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WITENBLAUW... Magical Beach Front Estate on Pelican Key
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
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SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Popular Beachfront property/ Barefoot in SXM
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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ROYAL PALM BEACH #101 ... 3 BR beachfront resort! Close to restaurants & shoppi
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Pelican Key 1Bedroom For Rent
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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The Blue Frenchie: Gorgeous 2-story townhouse in Pelican Key, St. Maarten
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, All pools
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FAJA LOBIE... Completely Updated Beachfront Villa on Burgeoux Bay
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Studio in Pelican Key Paradise
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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BEACH SECRET... Modern 4 BR beauty on Burgeaux Bay, walk to Maho!
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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SURFSONG VILLA-NEW LUXURY WATER FRONT VILLA-6 BEDS, also available in 4 and 5 be
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, All pools
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VILLA VITTORIA... Spectaculer, RARE 6BR villa sits directly on Simpson Bay Beach
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to restaurant
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps, All pools
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PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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TARA... Affordable oceanfront villa, walk to beach
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Encanto -2 Bedroom Beachfront Condo in Simpson Bay, Sint Maarten -GORGEOUS VIEW!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Villa Ocean Breeze - Private Pool - 2 Masters - Private Courtyard
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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LA DI DA...4BR Hilltop Villa Overlooking Pelican Key
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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SUR MER... Rare 3BR beachfront condo at Coco's Beach Club on Simpson Bay!
Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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INFINITY AT OCEAN EDGE...3 BR Condo Beacon Hill, St. Maarten
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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A breathtaking view
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Beachfront Condo
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Beach view
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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SURFSONG... 6BR fall in love again! Breathtaking sunsets, directly on ocean!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
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Ocean Front with Private Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key
Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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THE DREAM at Los Arenas... Fabulous Beachfront Penthouse on Simpson Bay
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Steps to Caribbean, pool and 2 mile-long beach
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, All pools
More info
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Brand New House Indigo Bay beach, St Maarten
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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1Bedroom in Pelican Key
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
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Comfy Studio w/ WiFi, Beach Access, Resort Pool & More!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Ocean View Studio w/ WiFi, Resort Casino, Pools & Beach Access
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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LIFE'S A BEACH... Indeed! Remodeled beachfront, great location on Simpson Bay
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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