Title: Cupecoy Vacation Home Rentals from CA $134: Search Top Private Vacation Homes for Rent | Expedia.ca

[Cupecoy Travel Guide](https://expedia.ca/Cupecoy.dx602829)[Hotels in Cupecoy](https://expedia.ca/Cupecoy-Hotels.d602829.Travel-Guide-Hotels)[Vacation Rentals in Cupecoy](https://expedia.ca/Cupecoy-Vacation-Rentals.d602829.Travel-Guide-VacationRentals)[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)

![](https://images.trvl-media.com/place/602829/6c10b508-efda-4cc7-b1ef-b851143c9bef.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=602829&startDate=2026-06-19&endDate=2026-06-21&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 homes

![Deluxe Apartment, Courtyard View](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/799a8d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, Courtyard View | Bathroom](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/2783b5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, Courtyard View](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/9f89af05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, Courtyard View | Bathroom](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/78908937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Philips Scott House Calinago

[](https://www.expedia.ca/Philipsburg-Hotels-Philips-Scott-House-Calinago.h125096555.Hotel-Information)

Downtown Philipsburg

CA $233

CA $348 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Philipsburg-Hotels-Philips-Scott-House-Calinago.h125096555.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)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/45000000/44550000/44548100/44548053/e3aad0d7.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)

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

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

[](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

(11 reviews)

"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

Mar 11 - Mar 12

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

![Living area](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/w610h637x0y0-cdffcf87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/w678h684x0y0-f929a2f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/w859h584x0y0-240e9ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/1a1d41e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet cozy flat in the centre of the island.

[](https://www.expedia.ca/Cul-De-Sac-Hotels-Quiet-Cozy-Flat-In-The-Centre-Of-The-Island.h111777106.Hotel-Information)

Weymouth Hill, Sint Maarten

6.0/10

(3 reviews)

"They did not describe anywhere the access issues this property has. It’s up on a mountain and there is no proper walk up. It is rough uneven concrete at an extremely steep angle. We had two small children and elderly people in our group. It was very dangerous and my children fell a few times down and hurt themselves even though we tried to be very careful. 2\. We were advertised to have two full bathrooms. Both bathrooms had cold water for several days. After complaining several times the owners...

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

Kat S.

CA $219

CA $294 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Cul-De-Sac-Hotels-Quiet-Cozy-Flat-In-The-Centre-Of-The-Island.h111777106.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855967/d6309c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855967/33e09d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855967/bfef3062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90860000/90856000/90855967/48f2d59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Novels Villa is a family-friendly home with the Caribbean Sea as your backyard.

[](https://www.expedia.ca/Grand-Case-Hotels-Family-Friendly-Home-With-The-Caribbean-Sea-As-Your-Backyard.h90855967.Hotel-Information)

Grand-Case

9.8/10

Exceptional

(18 reviews)

"The host was very welcoming, accommodations were wonderful and one could not ask for a better beach front location."

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

Al N.

[](https://www.expedia.ca/Grand-Case-Hotels-Family-Friendly-Home-With-The-Caribbean-Sea-As-Your-Backyard.h90855967.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103540000/103538300/103538262/w1024h582x0y59-63d8cd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103540000/103538300/103538262/w506h683x259y0-714e3766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103540000/103538300/103538262/6dc3a7ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103540000/103538300/103538262/w506h683x259y0-9e7bde18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-Bedroom Loft Apartment in Point Blanche

[](https://www.expedia.ca/Philipsburg-Hotels-Apartment-Unit-In-Point-Blanche.h103538262.Hotel-Information)

Point Blanche

CA $154

CA $265 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/Philipsburg-Hotels-Apartment-Unit-In-Point-Blanche.h103538262.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/b8ad6100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/0dd143a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, offices, printers](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/099fc5a4.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/114000000/113250000/113245500/113245474/41f0653a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3BR Villa w Private Pool in Pelican Key

[](https://www.expedia.ca/Simpson-Bay-Hotels-Charming-3BR-Villa-W-Private-Pool-In-Pelican-Key.h113245474.Hotel-Information)

Pelican Key

CA $632

CA $1,223 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Simpson-Bay-Hotels-Charming-3BR-Villa-W-Private-Pool-In-Pelican-Key.h113245474.Hotel-Information)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/120000000/119540000/119532500/119532448/w1152h854x63y61-ff72d1d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/120000000/119540000/119532500/119532448/bb43a447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/120000000/119540000/119532500/119532448/w1126h827x0y0-1e84feaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heart of SXM! Mingle with the Locals!

[](https://www.expedia.ca/Cole-Bay-Hotels-Heart-Of-SXM-Mingle-With-The-Locals.h119532448.Hotel-Information)

Cay Bay

CA $234

CA $320 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Cole-Bay-Hotels-Heart-Of-SXM-Mingle-With-The-Locals.h119532448.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598339/314fafac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598339/3f7938d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598339/d63b94e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598339/c759e35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR Townhouse in Pelican Key w/ Pool & Beach Acess

[](https://www.expedia.ca/Cole-Bay-Hotels-Spacious-3BR-Townhouse-WPool-Near-BeachDining.h114598339.Hotel-Information)

Pelican Key

CA $748

CA $1,313 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Cole-Bay-Hotels-Spacious-3BR-Townhouse-WPool-Near-BeachDining.h114598339.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95050000/95050000/95049935/b4da5fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/96000000/95050000/95050000/95049935/faf717a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/96000000/95050000/95050000/95049935/67fa7283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95050000/95050000/95049935/e5882dad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Villa Salee - Full Villa Selection

[](https://www.expedia.ca/Cole-Bay-Hotels-La-Villa-Salee-Full-Villa-Selection.h95049935.Hotel-Information)

Pelican Key

CA $5,459

CA $6,791 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Cole-Bay-Hotels-La-Villa-Salee-Full-Villa-Selection.h95049935.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=2026-03-10&endDate=2026-03-11&regionId=602829&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_602829)

## Find vacation rentals that suit your style

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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA)

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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO)

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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=HOUSE_BOAT)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCupecoy-Private-Vacation-Homes.d602829-aaPrivateVacationHomes.Travel-Guide-Accommodation)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCupecoy-Private-Vacation-Homes.d602829-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Cupecoy Hotel Reviews

![Hilton Vacation Club Flamingo Beach St. Maarten](https://images.trvl-media.com/lodging/1000000/800000/796500/796441/67b50717_y.jpg)

### Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent

"Room very clean. Close to restaurants grocery stores and other beachesof you want to check them out. Beach on site is beautiful. Water is calm. Pool was very nice too!"

[](https://expedia.ca/Simpson-Bay-Hotels-Flamingo-Beach-Resort-By-Diamond-Resorts.h796441.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

"The room was great, beautiful view of the pool and ocean. Everything we the ate at the resort was great, the staff were also great. Would definitely stay here again :) Loved the little touches, like a rum punch and a hand/face towel when you check in."

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

"Staff was very friendly and welcoming. The rooms were clean and the food was great. "

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

![Hommage Hotel & Residences](https://images.trvl-media.com/lodging/36000000/35380000/35372900/35372844/cf07679d_y.jpg)

### Hommage Hotel & Residences

10/10 Excellent

"Great, staff was very helpful"

[](https://expedia.ca/Nettle-Bay-Hotels-Hommage-Hotel-Residences.h35372844.Hotel-Information)

![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/fee04e6c_y.jpg)

### Oceans at Divi Little Bay

10/10 Excellent

"The rooms were clean. The property was beautiful and there was plenty of activities to do. Food and bars were great too. The location was convenient "

[](https://expedia.ca/Philipsburg-Hotels-Oceans-At-Divi-Little-Bay.h74267774.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

"\*Modern clean rooms. \*Having a few dishes, microwave, mini-fridge turned out to be handy. \*Staff was very friendly. \*Breakfast buffet was excellent. \*Onsite restaurants and many nearby was nice. \*Broad selection at the Replay Restaurant & Bar. It was the only one we ate at twice. "

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

![JW Marriott St. Maarten Beach Resort & Spa](https://images.trvl-media.com/lodging/94000000/93240000/93232000/93231967/fd639aa3_y.jpg)

### JW Marriott St. Maarten Beach Resort & Spa

10/10 Excellent

"Great staff, spotless resort. Day manager, she was awesome. "

[](https://expedia.ca/Oyster-Pond-Hotels-The-Westin-Dawn-Beach-Resort-Spa.h93231967.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

"I do recommend to stay there view was nice also the staff were very nice and professional "

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

![Esmeralda Resort](https://images.trvl-media.com/lodging/1000000/30000/24700/24664/be01c4d4_y.jpg)

### Esmeralda Resort

10/10 Excellent

"Staff was excellent!"

[](https://expedia.ca/Orient-Bay-Hotels-Esmeralda-Resort.h24664.Hotel-Information)

## Find out more about Cupecoy

## Cupecoy Vacation Homes information

| Number of reviews | 21                 |
| ----------------- | ------------------ |
| Accommodation     | 249 Vacation Homes |
| Lowest Price      | CA $134            |
| Highest Price     | CA $6,791          |