Cupecoy Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cupecoy vacation rentals

10.0 out of 10, Exceptional, (24)
"Excellent stay enjoy this part of Sint Maarten.Studio was clean and in a great location."
Canada
Regis D.
$150 nightly
The price is $150
Jan 11 - Jan 12, 2026
Total with taxes and fees
Convenient studio close to airport, beaches and food
$666 nightly
The price is $694
Jan 12 - Jan 13, 2026
Total with taxes and fees
Happy Haven at Rainbow Beach Club
6.0 out of 10, (1)
"The location was excellent. We walked to restaurants and entertainment every night. The unit we had was very dimly lit. One hall light and 3 of 4 lamps worked but had low wattage bulbs. The dresser and closet were both full of owner's stuff. Don't lose your card key or you will be charged 10.00! The Sapphire is a great facilty, but the unit we had was not."
United States
Doug & Barb S.
$217 nightly
The price is $217
Jan 10 - Jan 11, 2026
Total with taxes and fees
Cozy studio in lovely St Maarten with WiFi, AC, fitness room
7.4 out of 10, Good, (3)
"Impressive unit! Clean, comfortable beds, well stocked kitchen.. We enjoyed the area, the food venues and the Friendly atmosphere. Close to the store. Short walk to the Lovely Mullet Bay Beach. Thank you Stacey and Jonathan!"
United States
Judy E.
$417 nightly
The price is $444
Jan 6 - Jan 7, 2026
Total with taxes and fees
* NEW LISTING* Oceanview 2BR-walking distance to Mullet bay Beach
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful condo! The management company is very accommodating and responsive. The location is great as well. A grocery store steps away and numerous restaurants, and walking distance to the beach. My teenage kids loved the pool. "
United States
Jamie H.
$1,034 nightly
The price is $1,080
Dec 26 - Dec 27
Total with taxes and fees
Luxury 3BR Penthouse W/ Huge Lagoon Pool
10.0 out of 10, Exceptional, (1)
"The condo is beautiful with an exceptional view. The condo was very well furbished with everything I needed including cooking and kitchen equipment and utensils. The close proximity to the Market makes buying groceries very convenient and it is located in my favorite part of the island. Quiet but a short drive to both the French and the Dutch sides great beaches and hot spots although the pools and private beach at the property are amazing. Having a parking garage so your car is in the shade is...
United States
Tony R.
$780 nightly
The price is $780
Dec 30 - Dec 31
Total with taxes and fees
Beachfront Escape/Rainbow 2BR
10.0 out of 10, Exceptional, (2)
"Mike was a great host"
United States
warren p.
$828 nightly
The price is $828
Dec 29 - Dec 30
Total with taxes and fees
Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton
$865 nightly
The price is $903
Jan 12 - Jan 13, 2026
Total with taxes and fees
2BR Sunset Condo at Blue Mall – Near Maho
$880 nightly
The price is $880
Dec 26 - Dec 27
Total with taxes and fees
Rare Gem: 3-Bedroom with Direct Pool Access & Peloton Bike!
10.0 out of 10, Exceptional, (2)
"Wow. We can’t say enough about this amazing experience. The hosts are wonderful. We were just on their fantastic boat for one night - the last night of our trip, but it was perfect. We had a sail out to Tintamarre, a pristine and beautiful little deserted (amd conservation protected) island. We snorkeled, had apps and Karim’s signature cocktail as the sun went down. Then Sophie served us a great dinner out on the deck of the boat, including her delicious homemade bread! We stargazed and slept...
United States
Sheri W.
$2,574 nightly
The price is $2,574
Jan 2 - Jan 3, 2026
Total with taxes and fees
Tintamarre exclusive dinner and night at anchor
$1,178 nightly
The price is $1,219
Jan 2 - Jan 3, 2026
Total with taxes and fees
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
$1,187 nightly
The price is $1,187
Jan 4 - Jan 5, 2026
Total with taxes and fees
Unusual night in catamaran with dinner

Aparthotel in Downtown Philipsburg

MIDTOWN MOTEL SXM
2.5 star property
8.0 out of 10, Very Good, (1)
"The staff was extremely helpful "
United States
Joycelyn
$81 nightly
The price is $85
Dec 27 - Dec 28
Total with taxes and fees
MIDTOWN MOTEL SXM

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.8 out of 10, Excellent, (55)
"Enjoyed my stay "
United States
Shakia
$265 nightly
The price is $277
Dec 24 - Dec 25
Total with taxes and fees
The Hills Residence

Aparthotel in Madame's Estate

July Apartments
3.0 star property
9.2 out of 10, Wonderful, (156)
"Amazing place. "
United States
Cristina
$77 nightly
The price is $80
Jan 1 - Jan 2, 2026
Total with taxes and fees
July Apartments

Aparthotel in Pelican Key

FLAMINGO BEACH
3.5 star property
$461 nightly
The price is $482
Jan 17 - Jan 18, 2026
Total with taxes and fees
FLAMINGO BEACH
$164 nightly
The price is $170
Jan 8 - Jan 9, 2026
Total with taxes and fees
Charming studio with splendid Caribbean Sea view & pool/beach access
4.0 star property
9.8 out of 10, Exceptional, (113)
"Fantastic place to stay. Clean, great views, excellent amenities"
Canada
Oleksii
$314 nightly
The price is $329
Dec 26 - Dec 27
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
9.0 out of 10, Wonderful, (9)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
$97 nightly
The price is $97
Jan 13 - Jan 14, 2026
Total with taxes and fees
Lovely room in a nice villa with a big garden, close to Friars bay beach

Apartment in Collectivité de Saint-Martin

Happy Residence - Orient Beach 09
9.6 out of 10, Exceptional, (5)
"The property was very nice. A few improvements like more bath towel's and beach towels would be nice."
United States
Joseph
$234 nightly
The price is $234
Dec 27 - Dec 28
Total with taxes and fees
Happy Residence - Orient Beach 09
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cupecoy Hotel Reviews

Find out more about Cupecoy

Everything you need to know about Cupecoy vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cupecoy vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cupecoy vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cupecoy vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cupecoy. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cupecoy in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cupecoy rentals

At Expedia, we put the best Cupecoy vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cupecoy rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cupecoy vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cupecoy. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Novels Villa is a family-friendly home with the Caribbean Sea as your backyard.: This vacation home rental near Cupecoy is located on the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Cupecoy?

Expedia has 9 vacation rentals for your stay in Cupecoy.

What’s there to see and do in Cupecoy?

Get outdoors into nature at a spot like Cupecoy Beach, or visit other top attractions such as Maho Beach. American University of the Caribbean and Mullet Bay Beach 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.