A coastal beach with clear turquoise waters, white buildings, and a rocky shoreline.

Cupecoy Vacation Rentals

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Our top choices for Cupecoy vacation rentals

1. Aventura Residences

Aventura Residences
Maho
9.6 out of 10, Exceptional, (16 reviews)
"Jen is a great host and her place is clean, modern and perfectly located. You’ll find everything for a pleasant stay on the island."
Canada
Nina R.
The price is CA $94
CA $199 total
includes taxes & fees
Sep 30 - Oct 1
Aventura Residences

2. Convenient studio close to airport, beaches and food

Convenient studio close to airport, beaches and food
Maho
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay"
Netherlands
john bracebridge w.
The price is CA $138
CA $224 total
includes taxes & fees
Sep 28 - Sep 29
Convenient studio close to airport, beaches and food

3. Fully furnish 1-Bedroom Apt. For Business, Leisure, providing safety & Comfort

Fully furnish 1-Bedroom Apt. For Business, Leisure, providing safety & Comfort
Maho
The price is CA $168
CA $196 total
includes taxes & fees
Sep 23 - Sep 24
Fully furnish 1-Bedroom Apt. For Business, Leisure, providing safety & Comfort

4. Penthouse Paradise: Ocean Views & Peloton

Penthouse Paradise: Ocean Views & Peloton
Maho
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful space, great location, communicative host. Would definitely recommend and would love to stay again. "
United States
Kara K.
The price is CA $295
CA $619 total
includes taxes & fees
Sep 23 - Sep 24
Penthouse Paradise: Ocean Views & Peloton

5. Seaside Serenity: Pools & Beach Access

Seaside Serenity: Pools & Beach Access
Maho
7.4 out of 10, Good, (3 reviews)
"Mike and Roz were so friendly and helpful. We thoroughly enjoyed our stay. We hope to return as soon as we can."
United States
Jim / Rita M.
The price is CA $258
CA $530 total
includes taxes & fees
Sep 23 - Sep 24
Seaside Serenity: Pools & Beach Access

6. Ocean Bliss: Balcony & Ocean Views

Ocean Bliss: Balcony & Ocean Views
Maho
8.0 out of 10, Very good, (2 reviews)
"Beautiful resort. Great location. Great value."
United States
Arthur
The price is CA $340
CA $649 total
includes taxes & fees
Sep 24 - Sep 25
Ocean Bliss: Balcony & Ocean Views

7. Oceanfront Haven: 3-Bedroom Caribbean Retreat

Oceanfront Haven: 3-Bedroom Caribbean Retreat
Maho
10.0 out of 10, Exceptional, (2 reviews)
"The place is enormous, and opens right onto a beautiful pool and gorgeous beach!"
United States
Charlie O.
The price is CA $431
CA $803 total
includes taxes & fees
Sep 23 - Sep 24
Oceanfront Haven: 3-Bedroom Caribbean Retreat

8. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (184 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is CA $347
CA $491 total
includes taxes & fees
Oct 3 - Oct 4
Mullet Bay Suites: Your Luxury Stay Awaits

9. Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!

Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!
Maho Bay
10.0 out of 10, Exceptional, (90 reviews)
"Great location!!"
United States
Jill W.
The price is CA $194
CA $313 total
includes taxes & fees
Sep 24 - Sep 25
Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!

10. Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,304 reviews)
"Perfect location."
United States
Andre
The price is CA $202
CA $249 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Vacation Club Royal Palm St. Maarten

11. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (165 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is CA $170
CA $190 total
includes taxes & fees
Sep 23 - Sep 24
Simpson Bay Suites

12. Sovereign Suites Maho | 2BR w/ Pool, Beach Gear

Sovereign Suites Maho | 2BR w/ Pool, Beach Gear
Simpson Bay
8.0 out of 10, Very good, (1 review)
"We were a bit disappointed in our initial assessment of this property. It was a bit hard to find as there is no actual address. With the help of some very kind neighbours we did locate the suite. We found the suite could use some updating. The ad mentions beach extras like beach towels and blanket etc. Those things were not in the suite. At least we never found them. One thing the ad does not mention is that the condo is second floor but 3 flights of stairs on a spiral staircase. Anyone with...
Canada
Tracy W.
The price is CA $179
CA $523 total
includes taxes & fees
Sep 23 - Sep 24
Sovereign Suites Maho | 2BR w/ Pool, Beach Gear

13. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (253 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is CA $130
CA $136 total
includes taxes & fees
Oct 1 - Oct 2
July Apartments

14. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (169 reviews)
"Very good"
United States
Alyssia
The price is CA $216
CA $377 total
includes taxes & fees
Oct 7 - Oct 8
The Hills Residence

15. Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is CA $112
CA $173 total
includes taxes & fees
Sep 24 - Sep 25
Lovely room in a nice villa , close to Friars bay and happy bay

16. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (73 reviews)
"It was a wonderful stay and experience"
United States
Yollanda
The price is CA $102
CA $122 total
includes taxes & fees
Sep 23 - Sep 24
MIDTOWN MOTEL SXM

17. Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
"Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating."
United States
Colleen M.
The price is CA $227
CA $334 total
includes taxes & fees
Oct 20 - Oct 21
Maho Beach House: Studio Getaway, Oceanfront Vibe

18. The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Simpson Bay
The price is CA $161
CA $293 total
includes taxes & fees
Sep 25 - Sep 26
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

19. Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"Home away from home "
United States
Trevayne
The price is CA $155
CA $301 total
includes taxes & fees
Sep 24 - Sep 25
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

20. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $168
CA $209 total
includes taxes & fees
Sep 24 - Sep 25
The Castle ᴷ
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cupecoy Hotel Reviews

Find out more about Cupecoy

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cupecoy. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Cupecoy?

Yes, we have vacation rentals close to top points of interest in Cupecoy, or you can choose a more remote option if you're looking for a relaxing stay. Visitors to Cupecoy speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the cafes and shopping during your trip.

What are some of the best vacation home rentals that Cupecoy has to offer?

Philips Scott House Calinago: Located near Cupecoy, this vacation home rental is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals are there in Cupecoy?

Expedia has 11 vacation rentals for your stay in Cupecoy.

What’s there to see and do in Cupecoy?

While you're exploring the area, Maho Beach and Mullet Bay Beach are a couple of picturesque spots to get outside and enjoy nature. American University of the Caribbean and Mullet Bay are a couple of places you'll find in the larger area.

What’s a vacation rental in Cupecoy like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Cupecoy. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.