35 Best Vacation Rentals in Cupecoy Bay - Holiday Lettings - Cabins

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Cupecoy Bay

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38 Vacation rentals

24

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to Carisa one of the most exquisite villas in St. Martin situated directly on the stunning Baie Rouge Beach. This spectacular beach front property offers the most incredible views of the pristine white sandy beach and sea beyond. Carisa is a luxurious on …see more

from $1357 / night

$9500 - $19000 / week

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from $1357 / night

24

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to villa Ambiance, our luxurious 4 bedroom property located on the hillside of Terres Basses overlooking the Caribbean Sea. It is a fantastic family retreat and the perfect villa to spend a special occasion. The pool at Villa Ambiance is simply stunning and is t …see more

from $1071 / night

$7500 - $22000 / week

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from $1071 / night

28

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to our beautiful villa Sea Dream located on the hillside in Happy Bay. It is a gorgeous villa and only a 5 minute walk from the beach at Happy Bay. Friar's Bay is also very close and has 2 beach restaurants that are very popular with guests. The …see more

from $386 / night

$2700 - $5900 / week

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from $386 / night

24

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Casa Cervo, one of the St Martin's most exquisite and luxurious Beach Front Villa. This stunning 4+1 bedroom ultra luxurious property with private pool has the most incredible views looking out onto Baie Rouge Bay, one of the most beautiful beaches in St Mart …see more

from $1195 / night

$8365 - $28000 / week

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from $1195 / night

(2) Excellent 

23

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Welcome to The Retreat located in Shore Pointe, one of the newest and most exquisite developments and situated directly on the stunning beach at Cupecoy. This spectacular 4 bedroom ultra luxurious fully air conditioned property with private pool and Jacuzzi off …see more

from $930 / night

$6500 - $19000 / week

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from $930 / night

(3) Very Good 

24

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Welcome to Mumbai located in Shore Pointe, one of the newest and most exquisite developments and situated directly on the stunning beach at Cupecoy. This spectacular 3 bedroom ultra luxurious fully air conditioned property with private offers the most incredible views o …see more

from $815 / night

$5700 - $15500 / week

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from $815 / night

5

Cupecoy Bay Vacation apartment rental

Sint Maarten / Cupecoy Bay

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Suite "Caribbean Sea" is composed of a kitchen and a living area, and an area of ​​about 40 m². Furniture, tropical style, are natural rattan or white. A large terrace with private Jacuzzi, facing the Caribbean Sea The kitchen area includes an American fridge, hob, …see more

from $369 / night

$2577 / week

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from $369 / night

11

Vacation condo with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful beaches , restaurants and grocery stores are within walking distance . Airport is 2 miles away. The YouTube sensation airport is very entertaining spot to watch airplanes landing and their take offs. Clean and warm water is St Maarten's greatest attractions. …see more

from $300 / night

$2100 / week

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from $300 / night

(1) Excellent 

15

Vacation apartment with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Beautiful three bedroom, 3 � bath condo located in the Cupecoy area development known as Porto Cupecoy St. Maarten, close to French St. Martin-2 minutes drive to the border. Breathtaking view of Simpson Bay Lagoon and of romantic village marina and seaside piazza to the …see more

from $295 / night

$2071 - $6523 / week

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from $295 / night

9

Cupecoy Bay Vacation villa rental

Sint Maarten / Cupecoy Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning
This beautiful ocean view villa is in the popular Cupecoy Beach area, close to the new Blue Mall, Casinos, AUC, and Mullet Bay Beach. The villa has 3 floors, with 2 bedrooms/2 bathrooms on the 2nd and the 3rd bedroom/bathroom on the top/3rd floor. Villa can be rented wi …see more

from $675 / night

$3600 - $4700 / week

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from $675 / night

(1) Excellent 

26

Vacation apartment rental

Sint Maarten / Cupecoy Bay

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Aazure is located on the third floor of Building #7 in the gated complex of Porto Cupecoy and is rented as a one bedroom unit that comfortably sleeps up to four people. The master bedroom is furnished with a King size bed as well as a comfortable leather couch that con …see more

from $226 / night

$1600 / week

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Responds fast!
avg. 1 hour 11 minutes

from $226 / night

(2) Excellent 

13

Vacation private room in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cupecoy Beach Club unit 208 second floor deluxe oceanfront hotel room with private oceanfront balcony including daily maid service.. Located within step to complex large freshwater pool with swim up bar. Complex is a gated community with 24 hour security. Resort is loc …see more

from $150 / night

$900 - $1600 / week

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from $150 / night

10

Vacation apartment with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
It's a one bedroom, one bathroom 1000 sq ft condo on Cupecoy Beach. It's on the sixth floor looking over the pool and villas to the island of Saba. On good days, Statia and St Kitts are also visible. The bedroom on the other end of the unit looks out at the lagoon, Sand …see more

from $143 / night

$1001 - $1600 / week

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from $143 / night

22

Apartment rental in Cupecoy Bay with swimming pool

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
With a stunning backdrop of ocean and sky, La Perla Sky is a beautiful 2 bedroom penthouse apartment located right at the top of Porto Cupecoy village in the Dutch lowlands. Enjoying an almost unobstructed view of the island and coastline, the apartment has a rooftop te …see more

from $570 / night

$3990 - $7000 / week

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from $570 / night

22

Condo rental in Cupecoy Bay with shared pool

Sint Maarten / Cupecoy Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cupecoy Beach Club Oceanfront second floor two bedroom condo unit with three private bathrooms and two oceanfront balconies within guarded condo complex. This unit can be rented three different ways as a two bedroom, one bedroom or deluxe hotel room all with daily maid …see more

from $300 / night

$2100 / week

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from $300 / night

(13) Excellent 

31

Cupecoy Bay Vacation apartment rental

Sint Maarten / Cupecoy Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
The Cliff at Cupecoy Beach is modern and one of the most upscale and desirable places to stay on St. Maarten. The Cliff is located on a cliff that has steps down to the Caribbean Sea. The water is so clear that you can see from our 4th floor balcony all the way through …see more

from $175 / night

$1500 - $4850 / week

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Responds fast!
avg. 1 hour 54 minutes

from $175 / night

22

Vacation home in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Cupecoy is ideally located near the beach in the Dutch Lowlands and only a few minutes from the restaurants, bars and shops of Maho Village. The house has been designed to provide the best villa experience, with a large terrace with a pool and a nice view over the …see more

from $485 / night

$3395 / week

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Responds fast!
avg. 3 hours 35 minutes

from $485 / night

(1) Excellent 

11

Vacation condo with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Cliff is a 5 Star Condominium in Sint Maarten. My Condo is 1,550 sq ft. It is a huge 1 bedroom 1 bath condo with a Beautiful ocean view. The Cliff is 5 years young. The Condominium is gated and also has an indoor pool, and lighted tennis court, fitness center, Di …see more

from $210 / night

$1470 - $2275 / week

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from $210 / night

(2) Excellent 

28

Cupecoy Bay Vacation home rental

Sint Maarten / Cupecoy Bay

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Ask about children
Blue Paradise Luxury, Cupecoy Sint Maarten Sint Maarten is a true gem in the Eastern Caribbean with Cupecoy Beach is one of the most desirable regions. The Blue Residence is a spectacular residence overlooking the cliffs of Cupecoy and the Caribbean Sea. Comes as a 2 be …see more

from $295 / night

$2065 - $3255 / week

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from $295 / night

7

Vacation studio in Cupecoy Bay

Sint Maarten / Cupecoy Bay

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Great island! Awesome beaches. Tax free shopping. Best jewellery deals anywhere. Enjoy the wide array of dining, night clubs and casinos. Ocean club has a very nice pool accompanied by a pool side bar/ restaurant. Ocean and beach are just 100 steps away. This is on th …see more

from $122 / night

$850 / week

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from $122 / night

24

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Ask about pets
Villa Aazure St Martin. Porto Cupecoy, located on the Dutch side of Sint Maarten, is renowned for yachting, shopping, and unparalleled culinary delights. The elegant one bedroom luxury condo Aazure in Porto Cupecoy is the ideal base from which to experience all that thi …see more

from $228 / night

$1600 - $3500 / week

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from $228 / night

20

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Luxury living is possible in a modern apartment, and especially when that apartment is the Villa Syriana at Porto Cupecoy. Tucked into the charming marina and lagoon area of Cupecoy, this three-story, premium villa has more than just a roomy feel and high quality decor. …see more

from $500 / night

$3500 - $7000 / week

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from $500 / night

30

Villa rental in Cupecoy Bay with swimming pool

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3 Bedroom Villa can be rented as a 2 Bedroom Villa at a special rate! This 3 bedroom Penthouse is meticulously appointed to make your stay at Porto Cupecoy an unbelievable experience. The private roof deck with private plunge pool and outdoor kitchen offers the mos …see more

from $429 / night

$3003 / week

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from $429 / night

22

Cupecoy Bay Vacation villa rental

Sint Maarten / Cupecoy Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 2 Bedroom Condo can be rented as a 1 Bedroom Condo at a special rate! Fabulous brand new apartment located at the Blue Residence in Cupecoy. With 2 bedrooms, the apartment occupies 2 floors with an impressive 180 degree view stretching from the ocean and Baie Longu …see more

from $315 / night

$2205 / week

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from $315 / night

20

Vacation villa accommodation

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Corfu at Porto Cupecoy, St Maarten. The luxury Corfu penthouse is located in the stunning Porto Cupecoy development St Maarten. This elegant three bedroom penthouse condo makes for an unbelievable Caribbean experience. Porto Cupecoy is an exclusive, Mediterranean inspir …see more

from $428 / night

$3000 - $7000 / week

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from $428 / night

27

Vacation penthouse with golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
SkyView Penthouse is located within the spectacular Porto Cupecoy condo development. There are five restaurants with-in the Porto Cupecoy mezzanine as well as a full service grocery/wine/liquor store on the property. Cupecoy beach is a one minute walk from the condo and …see more

from $250 / night

$1750 / week

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from $250 / night

33

Cupecoy Bay Vacation villa rental

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 3 Bedroom Villa can be rented as a 2 Bedroom Vi …see more

from $429 / night

$3003 / week

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from $429 / night

(2) Very Good 

48

Cupecoy Bay Vacation b&b rental

Sint Maarten / Cupecoy Bay

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
This luxury boutique B&B offers 5 unique bedrooms with King Size beds, tumbled marble showers with six inch rain shower heads and Rolex fixtures atop tumbled marble vanities with travertine basins. The rates quoted are per room per night for five king size bedrooms exc …see more

from $1000 / night

$6000 / week

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from $1000 / night

23

Cupecoy Bay Vacation villa rental

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
The chic and modern Villa Moonrise on St Martin is a sophisticated two-story condo located on the upper floors of the luxury Blue Mall in the exclusive Cupecoy area. The impressive new apartment showcases an impressive 180 degree view of the gorgeous Simpson lagoon, the …see more

from $314 / night

$2200 - $5800 / week

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from $314 / night

(6) Excellent 

31

Vacation apartment with shared pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Welcome to Tranquil Settings at Porto Cupecoy! St Maarten, (Sint Maarten) ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Luxury Condo nested in a gated community, seconds away from Cupecoy beach: 2 Bedrooms, 2.5 Baths (Sleeps 2-4) Rates: (choose be …see more

from $275 / night

$1925 / week

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from $275 / night

(1) Excellent 

9

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Villa Mare is located an elegant 1 bedroom condo located in the gorgeous and highly popular Porto Cupecoy, just steps away from the powdery white sand and shimmering aqua waters of Cupecoy Beach. Porto Cupecoy is an exclusive, Mediterranean inspired township and has som …see more

from $228 / night

$1600 - $3500 / week

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from $228 / night

(1) Excellent 

39

Vacation home in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Please check out the property video on YouTube Porto cupecoy unit 6a Apartment 6A at Cupecoy Yacht Club is the finest Mediterranean village type unit in this exclusive 5 star complex and on the island, combining classic sophistication and Caribbean comfort with modern …see more

from $400 / night

$2800 / week

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Responds fast!
avg. 18 minutes

from $400 / night

(1) Excellent 

42

Cupecoy Bay Vacation penthouse rental

Sint Maarten / Cupecoy Bay

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This brand new 3 bedroom, 3.5 bath penthouse is simply the finest on the island. Comfortably sleeping 6. Spectacularly appointed. It's decorated with the top of the line of everything, comfortable, secure and totally relaxing. Views from both the terrace and the balcony …see more

from $2000 / night

$14000 / week

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Responds fast!
avg. 18 minutes

from $2000 / night

10

Apartment rental in Cupecoy Bay with golf nearby

Sint Maarten / Cupecoy Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning
Located on the fifth floor of the residence, our cozy 1 bedroom apartment has very nice views on the surroundings and the ocean. A few steps only from the Mullet Bay beach, this residence is centrally located with an easy access to restaurants, cafés and a grocery store …see more

from $75 / night

$525 / week

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Responds fast!
avg. 3 hours 35 minutes

from $75 / night

22

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 2 Bedroom Condo can be rented as a 1 Bedroom Condo at a special rate! Fabulous brand new apartment located at the Blue Residence in Cupecoy. With 2 bedrooms, the apartment occupies 2 floors with an impressive 180 degree view stretching from the ocean and Baie Longu …see more

from $358 / night

$2506 / week

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from $358 / night

30

Cupecoy Bay Vacation apartment rental

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
With 3 waterfront terraces, this 3 bedroom residence has incredible views over the water of Simpson Bay lagoon and the mega yacht slips of Porto Cupecoy’s marina. Nautilus has a bright and airy living room opening to a large outside living terrace complete with pergola …see more

from $371 / night

$2600 / week

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from $371 / night

25

Apartment rental in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Cupecoy Twilight is a Two bedrooms and three bathroom Condo located in Cupecoy Beach Club resort. This large and airy unit is tastefully redone with a modern twist. With two large bedrooms with en suite bathrooms, a large living room, spacious and open kitchen and terr …see more

from $243 / night

$1700 / week

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from $243 / night

17

Vacation apartment in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Indigo Cliff is a recently renovated unit located at Cupecoy Beach Club, a beach front complex on the Caribbean side of the island. Cupecoy Beach Club gated resort is a former hotel now offering its large and well located units to lucky visitors. It is a 24 hour gated …see more

from $199 / night

$1395 / week

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from $199 / night