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

Cupecoy Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cupecoy vacation rentals

A rectangular swimming pool with a white and blue structure nearby.

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.
Aventura Residences
A balcony with a view of residential buildings and palm trees.

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.
$171 nightly
The price is $171
Sep 24 - Sep 25
Total with taxes and fees
Convenient studio close to airport, beaches and food
A rooftop terrace with a view of the sea, string lights, and outdoor furniture.

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

Fully furnish 1-Bedroom Apt. For Business, Leisure, providing safety & Comfort
Maho
$140 nightly
The price is $140
Sep 24 - Sep 25
Total with taxes and fees
Fully furnish 1-Bedroom Apt. For Business, Leisure, providing safety & Comfort
A beach with clear turquoise water, sandy shore, and a rocky cliff.

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.
$458 nightly
The price is $458
Sep 24 - Sep 25
Total with taxes and fees
Penthouse Paradise: Ocean Views & Peloton
A bedroom with a bed, a wooden wardrobe, a nightstand, and a wall with a tropical painting.

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.
$393 nightly
The price is $393
Sep 24 - Sep 25
Total with taxes and fees
Seaside Serenity: Pools & Beach Access
A clear turquoise sea with a staircase leading to a beach, surrounded by palm trees.

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
$466 nightly
The price is $466
Sep 24 - Sep 25
Total with taxes and fees
Ocean Bliss: Balcony & Ocean Views
A coastal hotel with a balcony overlooking turquoise waters, a staircase leading to the beach, and a clear view of the sea.

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.
$599 nightly
The price is $599
Sep 24 - Sep 25
Total with taxes and fees
Oceanfront Haven: 3-Bedroom Caribbean Retreat
A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

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
$344 nightly
The price is $356
Oct 1 - Oct 2
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
A resort with a pool area, sun loungers, and umbrellas.

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.
$227 nightly
The price is $227
Sep 24 - Sep 25
Total with taxes and fees
Tropical Gem! Watch Jets Fly into Airport+Ocean Beach+Garden Views+MANY PERKS!!!
A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

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, (1,305 reviews)
$169 nightly
The price is $177
Oct 4 - Oct 5
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
A high-rise hotel with a view of the sunset over a marina.

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
$130 nightly
The price is $136
Sep 25 - Sep 26
Total with taxes and fees
Simpson Bay Suites
A living room with a sofa, coffee table, and chairs, a dining table with chairs, large windows, and artwork on the walls.

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.
$342 nightly
The price is $357
Sep 24 - Sep 25
Total with taxes and fees
Sovereign Suites Maho | 2BR w/ Pool, Beach Gear
A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

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
$93 nightly
The price is $97
Sep 24 - Sep 25
Total with taxes and fees
July Apartments
A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

14. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
$251 nightly
The price is $263
Oct 7 - Oct 8
Total with taxes and fees
The Hills Residence
A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

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
$124 nightly
The price is $124
Sep 24 - Sep 25
Total with taxes and fees
Lovely room in a nice villa , close to Friars bay and happy bay
A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

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
$80 nightly
The price is $83
Oct 5 - Oct 6
Total with taxes and fees
MIDTOWN MOTEL SXM
A wooden deck leading to a beach with clear turquoise water and a rocky shoreline.

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.
$243 nightly
The price is $243
Oct 20 - Oct 21
Total with taxes and fees
Maho Beach House: Studio Getaway, Oceanfront Vibe
A beach with clear turquoise water, a sandy shore, and a row of multi-story hotels in the background.

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

The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Simpson Bay
$206 nightly
The price is $212
Sep 25 - Sep 26
Total with taxes and fees
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
A balcony with white railings, a bench, and two chairs.

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
$218 nightly
The price is $218
Sep 24 - Sep 25
Total with taxes and fees
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
A compact kitchen with white cabinets, a stainless steel stove, a refrigerator, and a potted plant.

20. The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
$140 nightly
The price is $150
Sep 24 - Sep 25
Total with taxes and fees
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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

8/10 Good
"the Front Desk staff upon arrival at check in was very gd...Monique was Exceptional n very friendly n helpful also so professional"
KAREN 7-night trip
Posted less than an hour ago
Simpson Bay Resort, Marina & Spa

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 $83 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.

Explore a world of travel with Expedia

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.