Cupecoy Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Cupecoy vacation rentals

Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!

Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!
Maho
10.0 out of 10, Exceptional, (1 review)
"Beautiful resort. Great location. Great value."
United States
Arthur
The price is CA $358
CA $653 total
includes taxes & fees
Jun 30 - Jul 1
Beachside Retreat: Balcony, Pools, and Direct Ocean Access and Peloton!

Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton

Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton
Maho
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful space, great location, communicative host. Would definitely recommend and would love to stay again. "
United States
Kara K.
The price is CA $326
CA $616 total
includes taxes & fees
Jul 1 - Jul 2
Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton

Aventura Residences

Aventura Residences
Maho
9.8 out of 10, Exceptional, (13 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 $92
CA $198 total
includes taxes & fees
Jul 20 - Jul 21
Aventura Residences

Convenient studio close to airport, beaches and food

Convenient studio close to airport, beaches and food
Maho
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful stay"
Netherlands
john bracebridge w.
The price is CA $140
CA $239 total
includes taxes & fees
Jun 25 - Jun 26
Convenient studio close to airport, beaches and food

Cozy studio in lovely St Maarten with WiFi, AC, fitness room

Cozy studio in lovely St Maarten with WiFi, AC, fitness room
Maho
8.0 out of 10, Very good, (3 reviews)
"Large Studio with privacy diviser overlooking the pool and bar. Plenty of amenities including 5 beach chairs, umbrellas. Some food, coffee and condiments."
Canada
Donald D.
The price is CA $142
CA $241 total
includes taxes & fees
Jun 26 - Jun 27
Cozy studio in lovely St Maarten with WiFi, AC, fitness room

All-Inclusive Promotion: AUC September Term Student's 1 BR Fully-furnished, Wifi

All-Inclusive Promotion: AUC September Term Student's 1 BR Fully-furnished, Wifi
Maho
The price is CA $159
CA $187 total
includes taxes & fees
Jul 1 - Jul 2
All-Inclusive Promotion: AUC September Term Student's 1 BR Fully-furnished, Wifi

Oceanside Escape at Rainbow Beach Club – Pools, Views & Private Beach Access

Oceanside Escape at Rainbow Beach Club – Pools, Views & Private 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 $269
CA $548 total
includes taxes & fees
Jun 25 - Jun 26
Oceanside Escape at Rainbow Beach Club – Pools, Views & Private Beach Access

Rare Gem: 3-Bedroom with Direct Pool Access & Peloton Bike!

Rare Gem: 3-Bedroom with Direct Pool Access & Peloton Bike!
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 $478
CA $789 total
includes taxes & fees
Jul 1 - Jul 2
Rare Gem: 3-Bedroom with Direct Pool Access & Peloton Bike!

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Grand-Case
The price is CA $1,213
CA $1,435 total
includes taxes & fees
Jul 4 - Jul 5
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED

The Castle ᴷ

The Castle ᴷ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $170
CA $212 total
includes taxes & fees
Jun 26 - Jun 27
The Castle ᴷ

The Castle ᴶ

The Castle ᴶ
Downtown Philipsburg
10.0 out of 10, Exceptional, (1 review)
"Host was welcoming and the apartment was very clean and inviting. We will Definitely stay here again when we come back. "
United States
Neil C.
The price is CA $170
CA $212 total
includes taxes & fees
Jun 26 - Jun 27
The Castle ᴶ

The Castle f

The Castle f
Downtown Philipsburg
8.0 out of 10, Very good, (1 review)
"After a bit of confusion about checking in, we arrived and after that everything was great. It was a surprise to find the window was onto a corridor, but the air con was good so no need to open a window, and also helped to make the room quiet."
United Kingdom
Pat R.
The price is CA $170
CA $212 total
includes taxes & fees
Jun 26 - Jun 27
The Castle f

MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (63 reviews)
"Good rooms at a great location"
United States
Asheed
The price is CA $95
CA $116 total
includes taxes & fees
Jun 29 - Jun 30
MIDTOWN MOTEL SXM

The Castle ᴴ

The Castle ᴴ
Downtown Philipsburg
8.0 out of 10, Very good, (2 reviews)
"Absolutely great place to stay. Only downside is there is a bird that treats her 2 AM and then a rooster from about 5 AM to 9 AM so make sure you bring your earplugs."
United States
Denise W.
The price is CA $191
CA $235 total
includes taxes & fees
Jun 26 - Jun 27
The Castle ᴴ

July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (245 reviews)
"Great stay"
United States
Drunisha
The price is CA $111
CA $116 total
includes taxes & fees
Jun 25 - Jun 26
July Apartments

The Castle L - Twin Studio

The Castle L - Twin Studio
Downtown Philipsburg
The price is CA $170
CA $212 total
includes taxes & fees
Jun 25 - Jun 26
The Castle L - Twin Studio

Hillside Penthouse

Hillside Penthouse
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"Home away from home "
United States
Trevayne
The price is CA $159
CA $188 total
includes taxes & fees
Jul 2 - Jul 3
Hillside Penthouse

The Castle ᴳ

The Castle ᴳ
Downtown Philipsburg
The price is CA $170
CA $212 total
includes taxes & fees
Jun 25 - Jun 26
The Castle ᴳ

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, (1,245 reviews)
"Great staff.. Great location..Great property"
United States
Wilbert
The price is CA $203
CA $251 total
includes taxes & fees
Jul 18 - Jul 19
Hilton Vacation Club Royal Palm St. Maarten

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 $105
CA $134 total
includes taxes & fees
Jun 25 - Jun 26
Lovely room in a nice villa , close to Friars bay and happy bay
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

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.

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: This vacation home rental near Cupecoy 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 Casino Royale 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.