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Match: Waterfront
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$344
Match: Waterfront
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$655
“Super holiday at the Great Bay” Unfortunatly we have left Villa nr 2 past sunday after 12 wonderfull days! After the confirmation of our reservation we have never had a single doubt on this piece of heaven on earth, but it even exceeded all expectations!! Verry happy to stay here once more and already looking forward to that. This place is relaxing but has all comforts of a fully equiped villa on the other hand as well. Both Jim and Gina (on-site managers) do their very best to make the stay as comfortable as possible.
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$258
TARA... Affordable oceanfront villa, walk to beach
Simpson Bay villa
- 5 bedrooms
- 5 bathrooms
- sleeps 10
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$659
CORFU... Penthouse w/ Private Pool at Porto Cupecoy, St Maarten
Cupecoy Bay apartment
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$451
“Our 3rd anniversary” My husband and I had the pleasure of celebrating our 3rd wedding anniversary at Tranquil Settings! Absolutely loved this place and glad we spent it nestled in Port Cupecoy! Beautiful decor in every room, loved all aspects of Tranquil Settings! The cleanliness and comfort of each room was remarkable! The location is perfect, relaxed on the patio lounge chairs at night enjoying the wonderful view, the pool is just a short walk away, and enjoyed going to the plaza as well. Looking forward to visiting Tranquil Settings again - definitely my #1 choice for our 4th anniversary!!
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$286
LUNA at SHORE POINT... Secure, luxurious, and just steps from Cupecoy Beach
Cupecoy Bay house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$558
SEACHEST...Spacious, full AC, gorgeous views of Simpson Bay Lagoon
Cupecoy Bay villa
- 4 bedrooms
- 4 bathrooms
- sleeps 8
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$673
Best rated: SXM Panoramic Ocean View private villa w/exclusive private pool.
Philipsburg villa
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$402
Match: Waterfront
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$303
Gorgeous Beachfront Villa#9 at 'Villas on Great Bay'
Philipsburg apartment
- 2 bedrooms
- 3 bathrooms
- sleeps 6
Match: Waterfront
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$386
COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$230
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Simpson Bay villa
- 5 bedrooms
- 5 bathrooms
- sleeps 10
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$916
Dawn Beach Resort, Westin Penthouse for 8 Guests!
Oyster Pond penthouse
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$491
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$258
MARINA 360......Porto Cupecoy, overlooking Simpson Bay and the Marina, St Maarte
Cupecoy Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$401
Dawn Beach Club, St.Maarten - Ocean Front, next to JWMarriott property
Philipsburg apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 9
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$573
BAHARI... Fabulous beachfront villa, breathtaking sunsets!
Cupecoy Bay house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
“Amazing and relaxing” This home has everything! Great beaches, restaurants and shopping are all nearby but no need to leave the house. Beachfront, pool, amazing sunsets, designer furnishings, hot tub and state-of-the art kitchen, wireless network, music system, computer games and flat-screen televisions.. . including a huge outdoor television for night-time viewing from the pool! It is now our family's annual vacation spot!
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$851
3 bedroom Lux apartment in Dawn beach Club with private beach and infinity pool
Oyster Pond apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$410
CARIBBEAN PARADISE... Affordable 2BR condo at Rainbow Beach Club on the shores o
Cupecoy Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$181
MUMBAI... Elegant, Luxurious, Totally Secure, & private access to Cupecoy Beach!
Cupecoy Bay house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$816
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$524
AQUA VUE... Rare 4BR at Porto Cupecoy!..Huge Gym, Heated Pool, Tennis Courts, be
Cupecoy Bay apartment
- 4 bedrooms
- 4 bathrooms
- sleeps 8
Match: Waterfront
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$516
AGUA AZUL... Gorgeous 2BR at Porto Cupecoy, great location on the Gold Coast!
Cupecoy Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$287
HOPE COTTAGE... charming, romantic hideaway w/ breathtaking views!
Oyster Pond villa
- 1 bedroom
- 1 bathroom
- sleeps 2
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$216
MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$230
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t
Simpson Bay villa
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$559
ARCADIA...Charming hillside 3BR villa... wonderful sea & marina views
Oyster Pond house
- 4 bedrooms
- 4 bathrooms
- sleeps 6
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$504
BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key
Simpson Bay villa
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$501
WITENBLAUW... Magical Beach Front Estate on Pelican Key
Simpson Bay villa
- 6 bedrooms
- 7 bathrooms
- sleeps 17
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$2,432
ARTIMINO...3 BR condo, located in Porto Cupecoy, St Maarten
Cupecoy Bay apartment
- 3 bedrooms
- 4 bathrooms
- sleeps 6
Match: Waterfront
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$451
COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach
Simpson Bay condo
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Match: Waterfront
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$230
IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key
Simpson Bay apartment
- 3 bedrooms
- 4 bathrooms
- sleeps 6
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$430
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$443
La Calanthe. Amazing Ocean Front Villa, Pool, Direct ocean access
Cole Bay villa
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$631
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$344
NEW CONSTRUCTION -OCEANFRONT PROPERTY - 3 KING BEDROOMS - SLEEPS 8
Dawn Beach condo
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$492
FIVE MINUTES MORE... Fabulous contemporary villa overlooking Oyster Pond
Oyster Pond house
- 4 bedrooms
- 5 bathrooms
- sleeps 8
“Amazing Villa!” 7 of us stayed at this villa. Amazingly clean and the web photos don't do it justice. Re/max did a great job addressing a couple of minor issues. We would definitely stay here again!
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$800