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

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1,663 Vacation rentals

(3) Very Good 

24

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $814 / night

$5,700 / week

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from $814 / night

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 $1,357 / night

$9,500 / week

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from $1,357 / night

28

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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

$2,700 / week

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from $386 / night

(3) 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 $957 / night

$6,500 - $19,000 / week

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from $957 / 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 $1,071 / night

$7,500 / week

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from $1,071 / 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 $1,429 / night

$10,000 - $28,000 / week

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from $1,429 / 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 $386 / night

$2,702 / week

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from $386 / night

(1) Very Good 

26

Vacation apartment with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Figueira is a lovely 3 bedroom luxury condo at the new Porto Cupecoy Marina complex in Dutch St Maarten, just south of the French border. Located on the southwestern end of Simpson Bay lagoon and just across the street from Cupecoy Beach, Porto Cupecoy is a new develop …see more

from $558 / night

$3,900 - $4,900 / week

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from $558 / 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

$2,100 / week

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from $300 / night

14

Vacation home in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy. Cielo Azurro is a 2 bedroom, 2 bath high end penthouse condominium located at Rainbow Beach Club in Cupecoy - Unit #402. The Rainbow Beach Club is located directly on world famous Cupecoy Beach. This …see more

from $500 / night

$3,500 / week

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from $500 / night

(1) Excellent 

15

Vacation apartment with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • 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 th …see more

from $296 / night

$2,071 - $2,972 / week

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from $296 / night

(3) Excellent 

33

Vacation apartment in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy.Corfu is a 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 mo …see more

from $800 / night

$5,600 - $7,000 / week

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from $800 / night

(1) Excellent 

39

Vacation apartment 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
7th Night free Apr 15 - Dec 14, 2018Please inquire about lower rates offered for less than full occupancy.CARIBBEAN PEARL - named for the gem that it is - is in a perfect location within the exciting new Porto Cupecoy Marina Resort at Cupecoy Beach. This spacious 2 bedr …see more

from $400 / night

$2,800 - $3,900 / week

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from $400 / night

32

Vacation home with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy.Mumbai is a fully air-conditioned astonishing beach/waterfront rental property located in Shore Pointein Dutch St. Maarten.A Beautiful and Elegant gated community sitting on Cupecoy Beach - This beaut …see more

from $1,215 / night

$8,500 - $15,500 / week

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from $1,215 / night

24

Vacation apartment 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
NEW BOOKINGS ONLY every 7th Night is free! Sept 1 - Dec 14, 2018Please inquire about lower rates offered for less than full occupancy.Agua Azul is a luxurious 2 bedroom, 2.5 bathroom condo with breathtaking views of the Caribbean Sea, Simpson Bay and the Porto Cupecoy m …see more

from $700 / night

$4,900 / week

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from $700 / night

27

Vacation apartment in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
NEW BOOKINGS ONLY - 10% Discount!Travel window - Jan 6 - Apr 14, 20187 Night MinimumNEW BOOKINGS ONLY - Every 5th Night Free!Travel window - Apr 15 - Dec 14, 2018Please inquire about lower rates offered for less than full occupancy. This is a very SPECIAL RESIDENCE know …see more

from $700 / night

$4,900 / week

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from $700 / night

21

Cupecoy Bay Vacation apartment rental

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Marina 360 is in one of the prime locations at the new Porto Cupecoy Marina Resort, sitting at the entrance to the Marina basin and surrounded by water. This lovely 2 bedroom 2 1/2 bath residence is housed on the entire top floor of a 2 story building and has 3 waterfro …see more

from $475 / night

$3,325 - $5,250 / week

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from $475 / night

(3) Excellent 

28

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
Villa Luna is a quiet oasis within the Shore Point beachfront villa community on the French/Dutch Border, in the town of Cupecoy. The all white villas make you feel as if you have landed in Greece and not St-Maarten. Villa Luna is set in the highest point of the communi …see more

from $557 / night

$3,899 / week

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Responds fast!
avg. 2 minutes

from $557 / night

40

Vacation apartment rental

Sint Maarten / Cupecoy Bay

4 8 10 nights min

  • 4 bedrooms
  • Sleeps 8
  • 10 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Chic & Modern! Immaculate! Affordable! Great Location!! Aqua Vue is a unique, luxurious 4 bedroom, 4.5 bathroom condo with breathtaking views of the Caribbean Sea and Simpson Bay and located in one of the most popular gated communities on the island! Nestled in a protec …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

32

Apartment rental in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
7th Night free Apr 15 - Dec 14, 2018Please inquire about lower rates offered for less than full occupancy. Aisling is a beautiful spacious apartment located in the Porto Cupecoy residence in Dutch St. Maarten with a fabulous view of Simpson Bay Lagoon and the mountains …see more

from $558 / night

$3,900 - $6,300 / week

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from $558 / night

26

Vacation apartment with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Modern apartment SKYMOON on St Martin is located on the very top of the prestigious Porto Cupecoy, allowing for guests to experience a breathtaking view of the shimmering blue ocean and matching pure blue sky(moon). Enjoying an almost unobstructed view of the island an …see more

from $638 / night

$4,469 - $7,840 / week

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Responds fast!
avg. 3 hours 22 minutes

from $638 / night

26

Vacation apartment with shared pool 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
Please inquire about lower rates offered for less than full occupancy.Island Breezes – Wonderful 2 bedroom, 2.5 bathroom condo located in Porto Cupecoy. The location within Porto Cupecoy is great as the views from the terrace are expansive taking in the wonderful views …see more

from $500 / night

$3,500 / week

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from $500 / night

7

Vacation studio in Cupecoy Bay

Sint Maarten / Cupecoy Bay

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
CURRENTLY UNAVAILABLE DUE TO IRMA 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 …see more

from $122 / night

$850 / week

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from $122 / 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

$2,065 - $3,255 / week

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from $295 / night

42

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Tiaris is one of The La Samanna Villas - a beautifully appointed 4 bedroom home located on a bluff overlooking Baie Longue with breathtaking views of the Caribbean Sea. The villa offers access to the excellent amenities at La Samanna Resort but with the privacy …see more

from $3,465 / night

$24,255 / week

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from $3,465 / night

(3) Excellent 

11

Vacation condo with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • 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

$1,470 / week

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from $210 / 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 $800 / night

$5,600 - $7,000 / week

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from $800 / 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 / week

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from $150 / 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

$2,100 / week

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Responds fast!
avg. 1 hour 18 minutes

from $300 / night

14

Vacation apartment 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
Caribbean Paradise is a beautifully furnished, spacious 2 bedroom, 2 bath condominium located on the “Gold Coast” of St Maarten at the Rainbow Beach Club on the shores of Cupecoy.Perfect for a small family on a budget, you’ll enjoy all the wonderful features this home a …see more

from $280 / night

$1,960 - $2,500 / week

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from $280 / night

(5) Excellent 

29

Vacation condo 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
  • Nearest beach 0 mi
  • Swimming pool
Oasis at The Cliff: Oceanfront Luxurious, 'On-The-Sand', Modern Condo with Unobstructed, Breathtaking Caribbean Views on a private beach... EXPERIENCE...OASIS THE CLIFF Celebrate yourself and relax while creating a memorable vacation that offers clean, comfortable li …see more

from $250 / night

$1,750 / week

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from $250 / night

33

Villa rental in Cupecoy Bay with swimming pool

Sint Maarten / Cupecoy Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beachfront Property - You've discovered a place where piercing turquoise waters meet the deeper blue of the sky, and where elegance meets simplicity, and style meets perfect function. Welcome to Villa Gonz, a luxury Caribbean 3 Bedroom, 3.5 Bathroom villa at Shore Point …see more

from $143 / night

$1,000 - $5,500 / week

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from $143 / night

29

Vacation apartment rental

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Includes FREE CAR (Kia Picanto 4 passenger economy car) for the duration of your stay!! For travel up to Dec 15, 2018 - 5 night minimum – All gas, tax, insurance, and upgrade fees are charged to guest. Porto Blue is a St. Maarten vacation rental. Thisthree bedrooms, 3 …see more

from $558 / night

$3,900 - $6,300 / week

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from $558 / night

(11) Excellent 

42

Vacation home with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Includes FREE CAR (Kia Picanto 4 passenger economy car) for the duration of your stay!! For travel up to Dec 15, 2018 - 5 night minimum – All gas, tax, insurance, and upgrade fees are charged to guest. You've discovered a place where piercing turquoise waters meet the …see more

from $786 / night

$5,500 - $14,000 / week

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from $786 / night

18

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3 Bedroom Villa can be rented as a 1 or 2 Bedroom Villa at special rates!    Villa Luna is a fully air-conditioned villa with 3 interior-access bedrooms and a large open-concept living room/dining room/kitchen area. This beautifully furnished villa is loc …see more

from $459 / night

$3,213 / week

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from $459 / night

9

Cupecoy Bay Vacation villa rental

Sint Maarten / Cupecoy Bay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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 $515 / night

$3,600 / week

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from $515 / night

(1) Excellent 

22

Vacation apartment in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Air conditioning
New Booking Only - Every 5th Night Free!Apr 15 - Dec 14, 2018Aazure is a beautifully appointed 1 bedroom, 1 ½ bathroom condo overlooking the gardens and pool of Porto Cupecoy. Please click on the video to get a first hand look at this lovely condo and the Porto Cupecoy …see more

from $386 / night

$2,700 / week

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from $386 / night

32

Vacation villa with swimming pool 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 4 Bedroom Villa can be rented as a 2 or 3 Bedroom Villa at special rates! Farniente is a contemporary villa at the edge of the sea located in the private community of Shore Pointe right on the French/Dutch Border. This luxurious gated enclave is like a stylish gl …see more

from $707 / night

$4,949 / week

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from $707 / night

(3) Very Good 

21

Apartment rental in Cupecoy Bay with shared pool

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Tropical Waves is a luxury, hip 2 bedroom, 2.5 bath residence in Porto Cupecoy - just steps to the BEACH! The location within Porto Cupecoy is great as the views from the terrace are expansive taking in the wonderful views of the Marina, the plaza plus views of Simpson …see more

from $393 / night

$2,750 - $2,900 / week

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from $393 / night

28

Cupecoy Bay Vacation home rental

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy. You've discovered affordable luxury on the "Gold Coast" of St Maarten... Villa Luna is a beautiful, fully air-conditioned vacation villa rental located in the oceanfront gated community of Shore Poin …see more

from $786 / night

$5,500 - $10,500 / week

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from $786 / night