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

[Simpson Bay Travel Guide](https://expedia.ca/Simpson-Bay.dx8941)[Hotels in Simpson Bay](https://expedia.ca/Simpson-Bay-Hotels.d8941.Travel-Guide-Hotels)[Vacation Rentals in Simpson Bay](https://expedia.ca/Simpson-Bay-Vacation-Rentals.d8941.Travel-Guide-VacationRentals)[Flights to Simpson Bay](https://expedia.ca/Cheap-Flights-To-Simpson-Bay.d8941.Travel-Guide-Flights)[Things to do in Simpson Bay](https://expedia.ca/Things-To-Do-In-Simpson-Bay.d8941.Travel-Guide-Activities)[Simpson Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Simpson-Bay.d8941.Car-Rental-Guide)[Simpson Bay Vacation Packages](https://expedia.ca/Simpson-Bay.d8941.Destination-Travel-Guides)

![Kim Sha Beach showing general coastal views and a coastal town](https://images.trvl-media.com/place/6079645/4e72a445-56d2-45d3-858f-efcb71e137a2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6079645/4e72a445-56d2-45d3-858f-efcb71e137a2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Simpson Bay vacation homes

![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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113250000/113245500/113245474/eb5d9f22.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 $785

CA $1,431 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)

![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](https://images.trvl-media.com/lodging/126000000/125100000/125096600/125096555/4a7f45bf.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 $231

CA $345 total

includes taxes & fees

Feb 24 - Feb 25

[](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)

![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)

![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)

### 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

8.8/10

Excellent

(10 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 12 - Mar 13

[](https://www.expedia.ca/Grand-Case-Hotels-Lovely-Room-In-A-Nice-Villa-With-A-Big-Garden.h44548053.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 $232

CA $318 total

includes taxes & fees

Feb 14 - Feb 15

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

![Exterior](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/1a1d41e2.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)

![Living area](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/w844h583x0y0-2c8d6230.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 $217

CA $295 total

includes taxes & fees

Feb 19 - Feb 20

[](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/115000000/114600000/114598400/114598339/314fafac.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)

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

![3 bedrooms, desk, internet, bed sheets](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598339/87764dad.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 $683

CA $1,250 total

includes taxes & fees

Feb 23 - Feb 24

[](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)

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

![TV](https://images.trvl-media.com/lodging/96000000/95050000/95050000/95049935/97c66dd1.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 $5,417

CA $6,739 total

includes taxes & fees

Feb 15 - Feb 16

[](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=2026-02-27&endDate=2026-02-28&regionId=8941&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CONDO)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APART_HOTEL)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=HOUSE_BOAT)

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## Top Simpson Bay Hotel Reviews

![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

"Room was clean & well maintained with a nice ocean front view. Staff was courteous & professional. Breakfast ( included) was quite good with variety."

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

![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

"Everything was great "

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

![The Hills Residence](https://images.trvl-media.com/lodging/99000000/98230000/98230000/98229949/e557289d_y.jpg)

### The Hills Residence

10/10 Excellent

"Everything was exactly like the photos. Very clean and modern. "

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

"Absolutely beautiful resort. Great service, friendly staff. Our 2nd time staying at the resort and we would go there again!"

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

![Commodore Suites](https://images.trvl-media.com/lodging/16000000/15090000/15082100/15082011/acd4d986_y.jpg)

### Commodore Suites

10/10 Excellent

"Everything was Perfect, very Nice staff, location, my room was big and the kitchen was full equiped although we didn’t cook. Very close to two nice beaches "

[](https://expedia.ca/Simpson-Bay-Hotels-Commodore-Suites.h15082011.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

"Room was great. Staff consistently checked in to make sure we had everything. Communicating through text with front desk was easy and quick."

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

![Cocovaa](https://images.trvl-media.com/lodging/94000000/93840000/93830300/93830243/88a3afcc_y.jpg)

### Cocovaa

10/10 Excellent

"Place is spotless, well situated. Staff is friendly. Beach access with chairs and 10$ for umbrella. "

[](https://expedia.ca/Simpson-Bay-Hotels-Cocovaa.h93830243.Hotel-Information)

![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg)

### Simpson Bay Resort, Marina & Spa

10/10 Excellent

"Room was spacious and spotless. Staff was friendly and helpful. The pools were perfect!"

[](https://expedia.ca/Simpson-Bay-Hotels-Simpson-Bay-Resort.h1256868.Hotel-Information)

![Travel Inn Hotel](https://images.trvl-media.com/lodging/1000000/800000/794400/794333/4ea4d6f2_y.jpg)

### Travel Inn Hotel

10/10 Excellent

"Very clean. Near simpson bay beach and close to the airport. On main road with no sidewalk so not good for walking. Good for the 1 night stay we had coming from Anguilla and going to the airport the next day."

[](https://expedia.ca/Simpson-Bay-Hotels-Travel-Inn-Hotel.h794333.Hotel-Information)

## Find out more about Simpson Bay

## Simpson Bay Vacation Homes information

| Number of reviews | 11                |
| ----------------- | ----------------- |
| Accommodation     | 33 Vacation Homes |
| Lowest Price      | CA $134           |
| Highest Price     | CA $6,739         |