A hillside residential area with houses, a swimming pool, and mountains in the background.

Orient Bay Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Orient Bay vacation homes

A wooden deck with a dining area, kitchen, and potted plants.

1. To complete

To complete
Cul-de-Sac
10.0 out of 10, Exceptional, (1 review)
"Jamal is very helpful, great communication."
Canada
Abdal M.
The price is CA $71
CA $79 total
includes taxes & fees
Dec 6 - Dec 7
To complete
A compact kitchen with a refrigerator, stove, and microwave. There is a painting on the wall and a ceiling fan.

2. To complete

To complete
Grand Case
The price is CA $189
CA $205 total
includes taxes & fees
Nov 26 - Nov 27
To complete
A tent-style room with a bed, a wooden chair, a small table with a plant, a sink, and a mirror.

3. To complete

To complete
Cul-de-Sac
The price is CA $87
CA $94 total
includes taxes & fees
Nov 29 - Nov 30
To complete
A wooden deck with a dining area, kitchen, and potted plants.

4. To complete

To complete
Cul-de-Sac
The price is CA $77
CA $85 total
includes taxes & fees
Nov 13 - Nov 14
To complete
A wooden deck with a dining area, kitchen, and potted plants.

5. To complete

To complete
Cul-de-Sac
The price is CA $77
CA $85 total
includes taxes & fees
Nov 18 - Nov 19
To complete
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

6. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is CA $194
CA $304 total
includes taxes & fees
Nov 11 - Nov 12
Philips Scott House Calinago
A spacious living room with a sofa, armchair, and a coffee table. There is a painting on the wall and a window providing a view.

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

Quiet cozy flat in the centre of the island.
Weymouth Hill, Sint Maarten
7.6 out of 10, Good, (5 reviews)
"Amazing view, Very friendly and helpful people. Only 1 thing is a must that's a SUV rental car. And some driving skills. But still a great spot to be spending your holiday."
Netherlands
Tobias
The price is CA $226
CA $289 total
includes taxes & fees
Nov 12 - Nov 13
Quiet cozy flat in the centre of the island.
A modern living room with a large TV, a wooden coffee table, a sofa, and a sliding glass door leading to an outdoor patio with a view of mountains.

8. C301 - Beautiful Lagoon View Apartment

C301 - Beautiful Lagoon View Apartment
Cole Bay
The price is CA $242
CA $460 total
includes taxes & fees
Nov 23 - Nov 24
C301 - Beautiful Lagoon View Apartment
A modern building with a glass balcony overlooking a coastal cityscape with mountains in the background.

9. C326 - Beautiful Apartment With Balcony

C326 - Beautiful Apartment With Balcony
Cole Bay
The price is CA $242
CA $460 total
includes taxes & fees
Dec 6 - Dec 7
C326 - Beautiful Apartment With Balcony
A modern living room with a large window offering a view of a coastal town and mountains.

10. D417 - One Bedroom Apartment with Lagoon View

D417 - One Bedroom Apartment with Lagoon View
Cole Bay
The price is CA $217
CA $430 total
includes taxes & fees
Nov 12 - Nov 13
D417 - One Bedroom Apartment with Lagoon View
The Hills Residence C-312 (8)

11. C312 - Charming Apartment with Balcony and View

C312 - Charming Apartment with Balcony and View
Cole Bay
The price is CA $242
CA $460 total
includes taxes & fees
Nov 11 - Nov 12
C312 - Charming Apartment with Balcony and View
A balcony with a view of a coastal city and mountains. There are two wicker chairs and a small table with a vase of flowers.

12. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is CA $242
CA $438 total
includes taxes & fees
Nov 15 - Nov 16
C344 - Lagoon view with balcony
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

13. The Luxe | Upscale 2BR Steps to Beach

The Luxe | Upscale 2BR Steps to Beach
Simpson Bay
The price is CA $255
CA $762 total
includes taxes & fees
Nov 11 - Nov 12
The Luxe | Upscale 2BR Steps to Beach
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

14. Tranquility | Luxury 2BR Steps to Beach

Tranquility | Luxury 2BR Steps to Beach
Simpson Bay
The price is CA $255
CA $785 total
includes taxes & fees
Nov 11 - Nov 12
Tranquility | Luxury 2BR Steps to Beach
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

15. Utopia | Luxury 2BR Steps to Simpson Bay Beach

Utopia | Luxury 2BR Steps to Simpson Bay Beach
Simpson Bay
The price is CA $282
CA $795 total
includes taxes & fees
Nov 19 - Nov 20
Utopia | Luxury 2BR Steps to Simpson Bay Beach
A modern living room with a flat-screen TV, a sofa, a coffee table, and a staircase.

16. Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood

Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
Cole bay
9.8 out of 10, Exceptional, (14 reviews)
"Private pool was definitely a plus for the heat and close to all the action"
United States
Anonymous traveller
The price is CA $522
CA $701 total
includes taxes & fees
Dec 9 - Dec 10
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
A beach with rows of sun loungers, palm trees, and a clear view of the ocean.

17. Nirvana | Modern 2BR Steps to Simpson Bay Beach

Nirvana | Modern 2BR Steps to Simpson Bay Beach
Simpson Bay
The price is CA $255
CA $785 total
includes taxes & fees
Nov 12 - Nov 13
Nirvana | Modern 2BR Steps to Simpson Bay Beach
A covered outdoor seating area with a view of the sea, featuring a sofa, chairs, and a table.

18. 3BR Townhouse in Pelican Key w/ Pool & Beach Acess

3BR Townhouse in Pelican Key w/ Pool & Beach Acess
Pelican Key
2.0 out of 10, (1 review)
The price is CA $363
CA $860 total
includes taxes & fees
Nov 11 - Nov 12
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
A swimming pool with a view of a marina and mountains.

19. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
The price is CA $242
CA $460 total
includes taxes & fees
Nov 11 - Nov 12
D402 - Beautiful apartment with garden and view
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.
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Top Orient Bay Hotel Reviews

La Playa Orient Bay

La Playa Orient Bay

10/10 Excellent
"We just returned from a wonderful stay at La Playa Orient Bay. The staff was wonderful from check-in to check out. The rooms were well appointed and the property was very well kept We were welcomed at breakfast every morning by a very cheerful Jerome, and welcome to our beach chairs every day by Michael and Tristan. The staff at reception was always there for any questions and anything we needed help with. Particularly Benedict, Clemmonse and Catherine. We will definitely return."
Katherine 6-night trip
Posted 11 hours ago
La Playa Orient Bay

Find out more about Orient Bay

Orient Bay Vacation Homes information

Number of reviews
15
Accommodation
48 Vacation Homes
Lowest Price
CA $79
Highest Price
CA $860