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

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2,232 Vacation rentals

(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 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 - $13,000 / week

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from $1,357 / night

(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 - $8,500 / week

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from $814 / 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 - $12,500 / 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 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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 - $16,500 / week

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from $1,429 / 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 - $4,000 / week

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from $386 / 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 $390 / night

$2,726 / week

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from $390 / 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
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $558 / night

$3,900 - $6,300 / week

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from $558 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $280 / night

$1,960 - $2,500 / week

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from $280 / 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
Additional amenities: Beach Towels, Concierge Service, Dock/Boat-slip, Full Kitchen, JetSki (Personal Watercraft) …see more

from $400 / night

$2,800 - $3,900 / week

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from $400 / 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

$2,600 / week

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from $371 / 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

22

Apartment rental in Cupecoy Bay with shared pool

Sint Maarten / Cupecoy Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
Lovely 2nd floor, 2 bedroom apartment at Porto Cupecoy with fabulous marina view. The apartment has a spacious light-filled living area and open –plan kitchen opening out to a covered terrace with waterfront views and ample space for dining and outdoor living. The 2 lar …see more

from $325 / night

$2,275 - $2,975 / week

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from $325 / 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

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
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $500 / night

$3,500 / week

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from $500 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $1,215 / night

$8,500 - $15,500 / week

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from $1,215 / night

38

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
  • Ask about children
  • Ask about pets
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 of St. Maarten in the background as well as the beautiful turquoise waters of the Caribbean Sea. With 3 lar …see more

from $410 / night

$2,870 - $3,900 / week

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from $410 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $475 / night

$3,325 - $5,250 / week

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from $475 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $558 / night

$3,900 - $6,300 / week

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from $558 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $500 / night

$3,500 / week

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from $500 / night

18

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
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 located in the p …see more

from $500 / night

$3,500 / week

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from $500 / night

(10) Very Good 

26

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
Mumbai’s exotic name reflects its exotic location, the private village of Cupecoy’s Shore Point right on the French/Dutch Border. Like an exquisite miniature version of a gleaming white Greek island, the villas of Shore Point are individual, elegant gems within a luxuri …see more

from $814 / night

$5,698 / week

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from $814 / 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
Additional amenities: Beach Towels, Dock/Boat-slip, Full Kitchen, JetSki (Personal Watercraft) …see more

from $800 / night

$5,600 - $7,000 / week

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from $800 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $1,000 / night

$7,000 / week

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from $1,000 / 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
Additional amenities: Beach Towels, Concierge Service, Dock/Boat-slip, Full Kitchen, JetSki (Personal Watercraft) …see more

from $800 / night

$5,600 - $7,000 / week

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from $800 / night

(1) Excellent 

27

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Full Kitchen, In-home Theater, JetSki (Personal Watercraft) …see more

from $1,143 / night

$8,000 - $13,500 / week

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from $1,143 / 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 - $1,600 / week

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from $150 / 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
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $700 / night

$4,900 / week

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from $700 / 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

$1,395 / week

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from $199 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $786 / night

$5,500 - $10,500 / week

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from $786 / night

26

Cupecoy Bay Vacation apartment rental

Sint Maarten / Cupecoy Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
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 Longue beach over Porto Cupecoy and all the way across Simpson Bay lagoon. The f …see more

from $358 / night

$2,500 - $4,000 / week

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from $358 / night

(2) 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

$1,470 - $2,275 / week

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from $210 / 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 th …see more

from $296 / night

$2,071 - $4,038 / week

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from $296 / night

27

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask about children
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 located in the private gated Shore Pointe development just steps from Cupecoy Beach and within …see more

from $557 / night

$3,900 - $5,500 / week

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from $557 / night

24

Vacation villa with shared pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 $325 / night

$2,275 - $3,325 / week

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from $325 / 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
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $393 / night

$2,750 - $2,900 / week

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from $393 / 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 an …see more

from $3,500 / night

$24,500 / week

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from $3,500 / night

(1) Very Good 

36

Cupecoy Bay Vacation apartment rental

Sint Maarten / Cupecoy Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
“Capri” is a stylish 3 bedroom apartment located in the Mediterranean-style village of Porto Cupecoy on Dutch St. Maarten. Overlooking the pool area of Porto Cupecoy, this beautifully decorated, light filled residence also has views over the marina, Simpson Bay lagoon a …see more

from $410 / night

$2,870 - $3,900 / week

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from $410 / night

40

Vacation villa rental

Sint Maarten / Cupecoy Bay

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
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 Bahari, a luxury Caribbean 3 Bedroom, 3.5 Bathroom villa at Shore Pointe at Cupecoy Beach. …see more

from $786 / night

$5,500 - $8,000 / week

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from $786 / 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
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $558 / night

$3,900 - $4,900 / week

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from $558 / night