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

Holiday Homes in Orient Bay

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Orient Bay holiday homes

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

1. To complete

To complete
Cul-de-Sac
The price is NZ$100
includes taxes & fees
29 Sept - 30 Sept
To complete
A covered patio with a table and chairs, surrounded by potted plants and overlooking a scenic view of hills and houses.

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

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is NZ$217
includes taxes & fees
28 Sept - 29 Sept
Lovely room in a nice villa , close to Friars bay and happy bay
A coastal landscape with a person standing near the water's edge, vegetation in the foreground, and a hilly background.

3. To complete

To complete
Cul-de-Sac
The price is NZ$120
includes taxes & fees
26 Sept - 27 Sept
To complete
A wooden deck with a dining area, kitchen, and potted plants.

4. To complete

To complete
Cul-de-Sac
The price is NZ$108
includes taxes & fees
2 Oct - 3 Oct
To complete
A beach with clear water, some scattered leaves, and houses in the background.

5. To complete

To complete
Grand Case
The price is NZ$213
includes taxes & fees
27 Sept - 28 Sept
To complete
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.

6. 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 NZ$368
includes taxes & fees
28 Sept - 29 Sept
Quiet cozy flat in the centre of the island.
A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

7. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is NZ$375
includes taxes & fees
5 Oct - 6 Oct
Philips Scott House Calinago
A covered outdoor area with a pool, chairs, and a table.

8. 1-Bedroom Loft Apartment in Point Blanche

1-Bedroom Loft Apartment in Point Blanche
Point Blanche
The price is NZ$288
includes taxes & fees
26 Sept - 27 Sept
1-Bedroom Loft Apartment in Point Blanche
A modern living room with a flat-screen TV, a sofa, a coffee table, and a staircase.

9. 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 NZ$816
includes taxes & fees
27 Sept - 28 Sept
Modern 3BR Home with Own Private Pool - Centrally Located - Quiet Neighborhood
A covered outdoor seating area with a view of the sea, featuring a sofa, chairs, and a table.

10. 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 NZ$1,048
includes taxes & fees
27 Sept - 28 Sept
3BR Townhouse in Pelican Key w/ Pool & Beach Acess
A modern living room with a grey sofa, a coffee table, and a dining area with chairs and a table.

11. Luxurious 3-Bedroom Townhome @ White Sands Beachfront Villas “Suite Serenity”

Luxurious 3-Bedroom Townhome @ White Sands Beachfront Villas “Suite Serenity”
Simpson Bay
The price is NZ$1,240
includes taxes & fees
29 Sept - 30 Sept
Luxurious 3-Bedroom Townhome @ White Sands Beachfront Villas “Suite Serenity”
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orient Bay Hotel Reviews

Palm Court Residence & Hotel at Orient Beach

Palm Court Residence & Hotel at Orient Beach

10/10 Excellent
"The staff was so courteous, the location was excellent, and we had such an excellent trip. I wish we had found this property earlier!"
David Brent 6-night trip
Posted 17 hours ago
Palm Court Residence & Hotel at Orient Beach

Find out more about Orient Bay

Orient Bay Holiday Homes information

Number of reviews
14
Accommodation
53 Holiday Homes
Lowest Price
NZ$100
Highest Price
NZ$1,240

Explore a world of travel with Expedia