Title: Cupecoy Vacation Rentals from CA $104: Short-Term Rentals for 2026 | Expedia.ca

[Cupecoy Travel Guide](https://expedia.ca/Cupecoy.dx602829)[Hotels in Cupecoy](https://expedia.ca/Cupecoy-Hotels.d602829.Travel-Guide-Hotels)[Things to do in Cupecoy](https://expedia.ca/Things-To-Do-In-Cupecoy.d602829.Travel-Guide-Activities)[Cupecoy Car Rentals](https://expedia.ca/Car-Rentals-In-Cupecoy.d602829.Car-Rental-Guide)[Cupecoy Vacation Packages](https://expedia.ca/Cupecoy.d602829.Destination-Travel-Guides)

![Cupecoy which includes a beach, landscape views and a luxury hotel or resort](https://images.trvl-media.com/place/602829/6c10b508-efda-4cc7-b1ef-b851143c9bef.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Cupecoy Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cupecoy vacation rentals

![Interior](https://images.trvl-media.com/lodging/40000000/39090000/39086200/39086127/4e85cf22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39090000/39086200/39086127/a1642632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39090000/39086200/39086127/7d7a427f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/40000000/39090000/39086200/39086127/55116f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Convenient studio close to airport, beaches and food

[](https://www.expedia.ca/Lowlands-Hotels-Convenient-Studio-Close-To-Airport.h39086127.Hotel-Information)

Maho

10/10

Exceptional

(24)

"Excellent stay enjoy this part of Sint Maarten.Studio was clean and in a great location."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Regis D.

CA $109

CA $205 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Lowlands-Hotels-Convenient-Studio-Close-To-Airport.h39086127.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/117000000/116780000/116776500/116776411/9f3bbdbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116780000/116776500/116776411/2da92c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116780000/116776500/116776411/cdf75101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/117000000/116780000/116776500/116776411/beb891a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Happy Haven at Rainbow Beach Club

[](https://www.expedia.ca/Lowlands-Hotels-Happy-Haven-At-Rainbow-Beach-Club.h116776411.Hotel-Information)

Maho

CA $474

CA $950 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Lowlands-Hotels-Happy-Haven-At-Rainbow-Beach-Club.h116776411.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107490000/107487800/107487763/w1160h733x8y9-5f93df8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107490000/107487800/107487763/85b44b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/108000000/107490000/107487800/107487763/757a2148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107490000/107487800/107487763/dbdee7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Lowlands-Hotels-Cozy-Studio-In-Lovely-St-Maarten-With-WiFi.h107487763.Hotel-Information)

Maho

6.0/10

(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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Doug & Barb S.

CA $191

CA $297 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Lowlands-Hotels-Cozy-Studio-In-Lovely-St-Maarten-With-WiFi.h107487763.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78280000/78276400/78276367/aa4456fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78280000/78276400/78276367/ba630e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78280000/78276400/78276367/634305fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78280000/78276400/78276367/1d764fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \* NEW LISTING\* Oceanview 2BR-walking distance to Mullet bay Beach

[](https://www.expedia.ca/Lowlands-Hotels-NEW-LISTING-Oceanview-2BR-Walking-Distance-To-Mullet-Bay-Beach.h78276367.Hotel-Information)

Maho

7.4/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Judy E.

CA $409

CA $618 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Lowlands-Hotels-NEW-LISTING-Oceanview-2BR-Walking-Distance-To-Mullet-Bay-Beach.h78276367.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598336/562ed3eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598336/ac74df0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598336/d7aff6de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598336/8e0ef44b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury 3BR Penthouse W/ Huge Lagoon Pool

[](https://www.expedia.ca/Lowlands-Hotels-Luxury-3BR-Penthouse-W-Private-Elevator.h114598336.Hotel-Information)

Maho

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jamie H.

CA $813

CA $1,477 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Lowlands-Hotels-Luxury-3BR-Penthouse-W-Private-Elevator.h114598336.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119510000/119505300/119505284/dc8308cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/120000000/119510000/119505300/119505284/d36c44cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119510000/119505300/119505284/fe4dc800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/120000000/119510000/119505300/119505284/813dd448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachfront Escape/Rainbow 2BR

[](https://www.expedia.ca/Lowlands-Hotels-Oceanfront-EscapeRainbow-2BR.h119505284.Hotel-Information)

Maho

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tony R.

CA $732

CA $1,061 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Lowlands-Hotels-Oceanfront-EscapeRainbow-2BR.h119505284.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67450000/67446100/67446041/7e88e55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/68000000/67450000/67446100/67446041/w508h683x258y0-825e3763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67450000/67446100/67446041/w907h683x58y0-8abca055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/68000000/67450000/67446100/67446041/01e0f3e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront Paradise: Luxurious Penthouse with Spectacular Pools and Peloton

[](https://www.expedia.ca/Lowlands-Hotels-Luxury-Apartment-In-Paradise-With-Peloton-Bike.h67446041.Hotel-Information)

Maho

10/10

Exceptional

(2)

"Mike was a great host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

warren p.

CA $776

CA $1,105 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Lowlands-Hotels-Luxury-Apartment-In-Paradise-With-Peloton-Bike.h67446041.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120270000/120267200/120267198/d90a3afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120270000/120267200/120267198/f5fc9b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/121000000/120270000/120267200/120267198/98545537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120270000/120267200/120267198/494bf89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Sunset Condo at Blue Mall – Near Maho

[](https://www.expedia.ca/Lowlands-Hotels-2BR-Sunset-Condo-At-Blue-Mall-Near-Maho.h120267198.Hotel-Information)

Maho

CA $665

CA $1,232 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Lowlands-Hotels-2BR-Sunset-Condo-At-Blue-Mall-Near-Maho.h120267198.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77120000/77114800/77114789/fbdb935d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/78000000/77120000/77114800/77114789/3fa92a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/78000000/77120000/77114800/77114789/af8c7d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/78000000/77120000/77114800/77114789/4cccaef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Lowlands-Hotels-Tropical-3-Bedroom-Paradise-On-Beach.h77114789.Hotel-Information)

Maho

CA $784

CA $1,117 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Lowlands-Hotels-Tropical-3-Bedroom-Paradise-On-Beach.h77114789.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106180000/106173900/106173882/f3a42573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106180000/106173900/106173882/442a3b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/107000000/106180000/106173900/106173882/5a568476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/107000000/106180000/106173900/106173882/ab5ebe0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tintamarre exclusive dinner and night at anchor

[](https://www.expedia.ca/Grand-Case-Hotels-Tintamarre-Exclusive-Dinner-And-Night-At-Anchor.h106173882.Hotel-Information)

Grand-Case

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sheri W.

CA $3,523

CA $3,523 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Grand-Case-Hotels-Tintamarre-Exclusive-Dinner-And-Night-At-Anchor.h106173882.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/d71c7292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/5ce29989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/02272588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/113000000/112720000/112711000/112710908/bc362754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Grand-Case-Hotels-Unique-Experience-Overnight-On-A-Catamaran-Cruise-With-Dinner-And-Breakfast.h112710908.Hotel-Information)

Grand-Case

CA $1,417

CA $1,669 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Grand-Case-Hotels-Unique-Experience-Overnight-On-A-Catamaran-Cruise-With-Dinner-And-Breakfast.h112710908.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/3751d8e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/55a1f511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/d75114c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, cookware/dishes/utensils](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372666/fd2c1d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unusual night in catamaran with dinner

[](https://www.expedia.ca/Grand-Case-Hotels-Unusual-Night-In-Catamaran-With-Dinner.h106372666.Hotel-Information)

Grand-Case

CA $1,625

CA $1,625 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Grand-Case-Hotels-Unusual-Night-In-Catamaran-With-Dinner.h106372666.Hotel-Information)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/6922e499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/844d9b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Queen Bed, Non Smoking, Beach View](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/6bacd041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Single Room](https://images.trvl-media.com/lodging/118000000/117900000/117899500/117899490/6727cc11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MIDTOWN MOTEL SXM

[](https://www.expedia.ca/Philipsburg-Hotels-MIDTOWN-MOTEL-SXM.h117899490.Hotel-Information)

Downtown Philipsburg

8.0/10

Very good

(1)

"The staff was extremely helpful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joycelyn

CA $100

CA $121 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Philipsburg-Hotels-MIDTOWN-MOTEL-SXM.h117899490.Hotel-Information)

![Amazing Top Floor Apartment | Balcony](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/cc64909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/2d3c4461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Exterior](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/64aa839e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beautiful 2 Bedroom - 2 Bathroom | Living area](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/3b4d9d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hills Residence

[](https://www.expedia.ca/Simpson-Bay-Hotels-69-Welfare-Rd.h98229949.Hotel-Information)

Simpson Bay

8.8/10

Excellent

(56)

"Enjoyed my stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shakia

CA $261

CA $424 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Simpson-Bay-Hotels-69-Welfare-Rd.h98229949.Hotel-Information)

![Deluxe Double Room](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/396a0e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/456bc93c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/2d70ac82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/85000000/84060000/84052400/84052377/ed07c974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### July Apartments

[](https://www.expedia.ca/Philipsburg-Hotels-July-Apartments.h84052377.Hotel-Information)

Madame's Estate

9.2/10

Wonderful

(156)

"Amazing place. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cristina

CA $99

CA $104 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Philipsburg-Hotels-July-Apartments.h84052377.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123310000/123305900/123305840/38a36798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123310000/123305900/123305840/7538d1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio Suite, Non Smoking | Terrace/patio](https://images.trvl-media.com/lodging/124000000/123310000/123305900/123305840/e102376b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Penthouse](https://images.trvl-media.com/lodging/124000000/123310000/123305900/123305840/49588ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FLAMINGO BEACH 

[](https://www.expedia.ca/Simpson-Bay-Hotels-FLAMINGO-BEACH.h123305840.Hotel-Information)

Pelican Key

CA $320

CA $660 total

includes taxes & fees

Jan 17 - Jan 18, 2026

[](https://www.expedia.ca/Simpson-Bay-Hotels-FLAMINGO-BEACH.h123305840.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/124000000/123520000/123514400/123514327/b392eb2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/124000000/123520000/123514400/123514327/82d1b87b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/124000000/123520000/123514400/123514327/2677b88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123520000/123514400/123514327/5070de23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming studio with splendid Caribbean Sea view & pool/beach access

[](https://www.expedia.ca/Marigot-Hotels-Charming-Studio-With-Splendid-Caribbean-Sea-View-Poolbeach-Access.h123514327.Hotel-Information)

Marigot

CA $196

CA $233 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Marigot-Hotels-Charming-Studio-With-Splendid-Caribbean-Sea-View-Poolbeach-Access.h123514327.Hotel-Information)

![702: Grand Apartment, 1 Queen Bed, Balcony, Sea View | Living area](https://images.trvl-media.com/lodging/100000000/99890000/99886200/99886151/dc851ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99890000/99886200/99886151/b17cd5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![802:Grand Apartment, 1 bedroom, 1 living room | Living area](https://images.trvl-media.com/lodging/100000000/99890000/99886200/99886151/e7c79f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99890000/99886200/99886151/6fff8d90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mullet Bay Suites: Your Luxury Stay Awaits

[](https://www.expedia.ca/Lowlands-Hotels-Mullet-Bay-Suites-Your-Luxury-Stay-Awaits.h99886151.Hotel-Information)

Maho

9.8/10

Exceptional

(114)

"Fantastic place to stay. Clean, great views, excellent amenities"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Oleksii

CA $288

CA $441 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Lowlands-Hotels-Mullet-Bay-Suites-Your-Luxury-Stay-Awaits.h99886151.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/835c2e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/5fa20b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/cb923536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/e00367b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely room in a nice villa with a big garden, close to Friars bay beach

[](https://www.expedia.ca/Grand-Case-Hotels-Lovely-Room-In-A-Nice-Villa-With-A-Big-Garden.h44548053.Hotel-Information)

Saint-martin

9.0/10

Wonderful

(9)

"Great place to stay. Will definitely be staying again next year! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kurt

CA $105

CA $134 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Grand-Case-Hotels-Lovely-Room-In-A-Nice-Villa-With-A-Big-Garden.h44548053.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66420000/66411500/66411409/1d464ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66420000/66411500/66411409/537ee2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66420000/66411500/66411409/df72a672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/67000000/66420000/66411500/66411409/4b64d899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Happy Residence - Orient Beach 09

[](https://www.expedia.ca/Orient-Bay-Hotels-Happy-Residence-Orient-Beach-09.h66411409.Hotel-Information)

Collectivité de Saint-Martin

9.6/10

Exceptional

(5)

"The property was very nice. A few improvements like more bath towel's and beach towels would be nice."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph

CA $210

CA $321 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Orient-Bay-Hotels-Happy-Residence-Orient-Beach-09.h66411409.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09&regionId=602829&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=VILLA)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Cupecoy%2C+Lowlands%2C+Sint+Maarten&regionId=602829&latLong=18.051424%2C-63.13268&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=HOUSE_BOAT)

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## Top Cupecoy Hotel Reviews

![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg)

### Divi Little Bay Beach Resort

10/10 Excellent

"Yes, very nice!!!"

[](https://expedia.ca/Philipsburg-Hotels-Divi-Little-Bay-Beach-Resort.h470827.Hotel-Information)

![Sonesta Maho Beach All Inclusive Resort Casino & Spa](https://images.trvl-media.com/lodging/1000000/570000/565700/565666/45414036_y.jpg)

### Sonesta Maho Beach All Inclusive Resort Casino & Spa

10/10 Excellent

"Despite the negative remarks, my family and I had a wonderful time! The pool was our favourite. The drinks and food also tasted really good. Our flight was 6pm and the staff allowed us to use the facilities (except the room which we were ok with) until 5pm which was a huge plus for us especially with kids. I would definitely recommend and would be back!"

[](https://expedia.ca/Lowlands-Hotels-Sonesta-Maho-Beach-All-Inclusive-Resort-Casino-Spa.h565666.Hotel-Information)

![Fourteen at Mullet Bay](https://images.trvl-media.com/lodging/83000000/82870000/82868300/82868222/7de7c76b_y.jpg)

### Fourteen at Mullet Bay

10/10 Excellent

"Great place to stay. We really enjoyed our time here. "

[](https://expedia.ca/Lowlands-Hotels-Fourteen-At-Mullet-Bay.h82868222.Hotel-Information)

![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg)

### Oyster Bay Beach Resort

10/10 Excellent

"Clean room. Good food. Beautiful."

[](https://expedia.ca/Oyster-Pond-Hotels-Oyster-Bay-Beach-Resort.h1095348.Hotel-Information)

![Seaview Beach Hotel](https://images.trvl-media.com/lodging/1000000/10000/4900/4848/72d983ac_y.jpg)

### Seaview Beach Hotel

10/10 Excellent

"Great service."

[](https://expedia.ca/Philipsburg-Hotels-Sea-View-Beach-Hotel.h4848.Hotel-Information)

![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg)

### The Villas at Simpson Bay Resort

10/10 Excellent

"Great accommodations and ocean view from the balcony. Close to great restaurants and bars. Overall a wonderful vacation. "

[](https://expedia.ca/Simpson-Bay-Hotels-The-Villas-At-Simpson-Bay-Beach-Resort-And-Marina.h4553784.Hotel-Information)

![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg)

### The Morgan Resort Spa Village

10/10 Excellent

"Room was spotless , friendly staff"

[](https://expedia.ca/Simpson-Bay-Hotels-The-Morgan-Resort-Spa-Village.h17524915.Hotel-Information)

![Royal Islander Resort La Plage](https://images.trvl-media.com/lodging/92000000/91180000/91176800/91176794/d9e0c970_y.jpg)

### Royal Islander Resort La Plage

10/10 Excellent

"Great view, nice pool, hot tub, nice beach with chairs, right next to the airport, fun watching planes land and take off!!! We loved this resort!!"

[](https://expedia.ca/Lowlands-Hotels-Royal-Islander-Resort-La-Plage.h91176794.Hotel-Information)

![Hilton Vacation Club Royal Palm St. Maarten](https://images.trvl-media.com/lodging/1000000/810000/807900/807815/ddd10394_y.jpg)

### Hilton Vacation Club Royal Palm St. Maarten

10/10 Excellent

"The stay was amazing! We were told when we arrived that our room was owned by a time share, and that we may have needed to move a coupe days into the trip. The hotel remedied this by offering an upgraded room and voucher for food at the restaurant for the inconvenience. We eventually didn’t need to move and were able to enjoy every amenities and the great view of the ocean water! Would very much recommend. The view was so beautiful!"

[](https://expedia.ca/Simpson-Bay-Hotels-Royal-Palm-Beach-Resort-By-Diamond-Resorts.h807815.Hotel-Information)

## 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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- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Apartments in Cupecoy ](https://expedia.ca/Cupecoy-Apartments.d602829-aaApartments.Travel-Guide-Accommodation)
- [Villas in Cupecoy ](https://expedia.ca/Cupecoy-Villas.d602829-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Cupecoy ](https://expedia.ca/Cupecoy-Condos.d602829-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Cupecoy?

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

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### What’s a vacation rental in Cupecoy like?

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Flights

- [YYZ to MCO flights](https://expedia.ca/lp/flights/yyz/mco/toronto-to-orlando)
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Cars

- [Car rental Hamilton Airport (YHM)](https://expedia.ca/Car-Rentals-In-John-C-Munro-Hamilton-Intl.d6033522.Car-Rental-Guide)

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