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

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=8941&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)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=8941&startDate=2026-06-12&endDate=2026-06-14&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)

![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)

![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 $651

CA $1,262 total

includes taxes & fees

Feb 24 - Feb 25

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

![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)

### Philips Scott House Calinago

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

Downtown Philipsburg

CA $231

CA $346 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Philipsburg-Hotels-Philips-Scott-House-Calinago.h125096555.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/91000000/90860000/90856000/90855967/9b739640.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

10/10

Exceptional

(16 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.

CA $409

CA $624 total

includes taxes & fees

Mar 18 - Mar 19

[](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/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)

![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 9 - Mar 10

[](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)

![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)

![Dining](https://images.trvl-media.com/lodging/112000000/111780000/111777200/111777106/w678h684x0y0-f929a2f5.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 $218

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)

![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)

![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)

![TV](https://images.trvl-media.com/lodging/96000000/95050000/95050000/95049935/97c66dd1.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 $5,433

CA $6,787 total

includes taxes & fees

Feb 23 - Feb 24

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

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103540000/103538300/103538262/b2179cd1.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)

![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 $153

CA $262 total

includes taxes & fees

Mar 18 - Mar 19

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

![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)

![Smart TV](https://images.trvl-media.com/lodging/115000000/114600000/114598400/114598339/d63b94e0.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 $753

CA $1,337 total

includes taxes & fees

Mar 10 - Mar 11

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

![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)

![Living area](https://images.trvl-media.com/lodging/120000000/119540000/119532500/119532448/bb43a447.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 $233

CA $319 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Cole-Bay-Hotels-Heart-Of-SXM-Mingle-With-The-Locals.h119532448.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=2026-03-02&endDate=2026-03-03&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

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&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=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Simpson+Bay%2C+Sint+Maarten&regionId=8941&latLong=18.037479%2C-63.096519&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&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=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&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=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&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=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=HOUSE_BOAT)

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## Top Simpson Bay Hotel Reviews

![The Atrium Beach Resort and Spa, an Ascend Collection Resort](https://images.trvl-media.com/lodging/2000000/1750000/1746400/1746391/3e2b89c6_y.jpg)

### The Atrium Beach Resort and Spa, an Ascend Collection Resort

10/10 Excellent

"We have stayed here for over ten years, staff always great rooms always clean and best place on the Island for us."

[](https://expedia.ca/Simpson-Bay-Hotels-Atrium-Beach-Resort-And-Spa-St-Maarten-A-Ramada-By-Wyndham.h1746391.Hotel-Information)

![La Vista Hotel](https://images.trvl-media.com/lodging/114000000/113160000/113158300/113158235/cde971ba_y.jpg)

### La Vista Hotel

10/10 Excellent

"Clean room, professional staff, and nice location"

[](https://expedia.ca/Simpson-Bay-Hotels-La-Vista-Hotel.h113158235.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

"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)

![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

"We will be back"

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

## Find out more about Simpson Bay

## Simpson Bay Vacation Homes information

| Number of reviews | 29                |
| ----------------- | ----------------- |
| Accommodation     | 33 Vacation Homes |
| Lowest Price      | CA $134           |
| Highest Price     | CA $6,787         |