Vacation Rentals & Villas in Cupecoy Bay

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CORFU... Penthouse w/ Private Pool at Porto Cupecoy, St Maarten

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$450

Tranquil Settings, Porto Cupecoy (1 Bedroom)

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

“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!!

Match: Walking trips

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Price per night from

$286

SEACHEST...Spacious, full AC, gorgeous views of Simpson Bay Lagoon

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$672

MARINA 360......Porto Cupecoy, overlooking Simpson Bay and the Marina, St Maarte

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$400

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!

Match: Walking trips

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Price per night from

$680

CARIBBEAN PARADISE... Affordable 2BR condo at Rainbow Beach Club on the shores o

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$180

AGUA AZUL... Gorgeous 2BR at Porto Cupecoy, great location on the Gold Coast!

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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Price per night from

$286

SEA BREEZE... Bright and Beautiful 3BR at Porto Cupecoy, St Maarten

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$545

SYRIANA... Penthouse in Porto Cupecoy, ocean, marina & lagoon views from private

Cupecoy Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$400

**AMAZING SPECIAL OFFERS PLEASE ENQUIRE** Mumbai - Cupecoy Beach - 3 Bedrooms

Cupecoy Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$814

**AMAZING SPECIAL OFFERS ** Villa Ambiance - Terres Basses - 4 Bedroom

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$1,143

**PLEASE ASK ABOUT OUR SPECIAL OFFERS** Casa Cervo - Baie Rouge 4 Bedrooms

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$1,643

LA PERLA SKY 3 BR PENTHOUSE...Porto Cupecoy, St Maarten

Cupecoy Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$650

DREAMS COME TRUE... Fabulous Oceanfront Penthouse at The Cliff on Cupecoy!

Cupecoy Bay condo

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$979

Great rentals within 20 miles that match your search

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Price per night from

$263

Villa ALLAMANDA in Guana Bay

Philipsburg villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Walking trips

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Price per night from

$1,373

MAEVA... Affordable, modern, completely new after Irma! Steps to beach!

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Walking trips

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Price per night from

$120

Match: Walking trips

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Price per night from

$183

BLUE SAILING.... Sweet affordable villa in Happy Bay. Endless Blue Views!

La Savane house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$485

VILLA MAPAI... Stunning oceanfront home, heated pool, full AC, kayaks!

Cul de Sac house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Walking trips

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Price per night from

$1,999

VILLA SILOVE... Oh so charming, affordable, and 2 min walk to Orient Beach!

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$258

GRANDE AZURE ... Spectacular 5 BR villa, views! huge heated pool, tennis, full A

Terres Basses villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$5,111

CASA DE LA PLAYA... Spectacular Baie Longue beachfront estate with Chef!

Terres Basses house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Walking trips

All filters match

Price per night from

$3,511

TUKAN... 4 min walk to Orient Beach!!

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

All filters match

Price per night from

$258

LES PALMIERS BLEUS... 5BR - Plum Baie beach, Private Tennis, Gym, heated pool!

Terres Basses villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Walking trips

All filters match

Price per night from

$1,284

Sabrina’s Caribbean Keys # 2

Quartier D'Orleans apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Walking trips

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Price per night from

$74

Match: Walking trips

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Price per night from

$558

AZUR...4BR located in the French Cul de Sac, facing Pinel Island, St Martin

Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$528

HORIZON SB... charming, renovated, ocean views and private pool!

Orient Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Walking trips

All filters match

Price per night from

$360

Apartment SUNRISE beautiful sea view / 2bedrooms

Cul de Sac apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$197

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$304

Match: Walking trips

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Price per night from

$296

Z'ABRICOT... Modern, Gorgeous! 4 min to Orient Beach!

Cul de Sac villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

Match: Walking trips

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Price per night from

$972

AVANTI... Gorgeous, Modern, 5 King suites, High-End through out!

Terres Basses house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Walking trips

All filters match

Price per night from

$1,999

COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$390

CORAL BEACH CLUB 9 - SORRENTO -...2 BR villa * Coral Beach Club on Dawn Beach

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$499

SIVIEW APARTMENT... Sweet beachfront condo on Orient beach

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$252

TI BLEU... charming, affordable apartment very close to Village Square & Orient

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Walking trips

All filters match

Price per night from

$120

Viewing 38 of 169
rentals in Cupecoy Bay

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