Orient Bay holiday rentals

We found 3,273 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Orient Bay by choosing from 65 houses, 31 flats and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Orient Bay

Showing deals for:20 Nov - 27 Nov

Room
Pool
Property grounds
Dining
Exceptional
(11 reviews)

Villa Oasis

Orient Bay

8% off
S$9,647
for 7 nights, 1 villa
S$1,378 per night
includes taxes & fees
Villa Oasis
Air Condition Living Room
Pool
In Door Dining Area
Just two minute walk to Plum Bay Beach
Exceptional
(32 reviews)

LUXURY 4 BEDROOM VILLA - JARDIN CREOLE TERRES BASSE - JUST TWO MINUTES TO BEACH

Les Terres Basses

8% off
S$14,292
for 7 nights, 1 villa
S$2,042 per night
includes taxes & fees
LUXURY 4 BEDROOM VILLA - JARDIN CREOLE TERRES BASSE - JUST TWO MINUTES TO BEACH
Room
Pool
Private kitchen
Property grounds
Exceptional
(17 reviews)

Luxurious Villa " Sea La Vie" in Pelican Key

Simpson Bay

5% off
S$6,137
for 7 nights, 1 villa
S$877 per night
includes taxes & fees
Luxurious Villa " Sea La Vie" in Pelican Key
Arial view of beach club. TRUE Condo location: 2nd floor blue roof.
Guests enjoy constant windward breezes at the ocean-facing pool. Just perfect!
Breakfast at LaSucriere Bread and Pastry Shop overlooking one of the bay areas.
Open concept dining and living area ideal for entertaining.
Exceptional
(5 reviews)

Steps from the beach- Luxe Condo-Coral Beach Club@ Dawn Beach ;Two Resort Access

Oyster Pond

14% off
S$3,030
for 7 nights, 1 apartment
S$433 per night
includes taxes & fees
Steps from the beach- Luxe Condo-Coral Beach Club@ Dawn Beach ;Two Resort Access
Very nice pool and deck.
Dining outside on lanai is the best!
Interior
Beach below resort
Wonderful
(10 reviews)

Beachfront Penthouse Best View Best location. Walk to best beaches and dining.

Lowlands

8% off
S$1,374
for 7 nights, 1 apartment
S$196 per night
includes taxes & fees
Beachfront Penthouse Best View Best location. Walk to best beaches and dining.
Room
Pool
Living area
Property grounds
Exceptional
(6 reviews)

Luxury Sea-View 2 Bedrooms, Duplex town house, Pool, private OrientBeach Access

Orient Bay

6% off
S$3,406
for 7 nights, 1 home
S$487 per night
includes taxes & fees
Luxury Sea-View 2 Bedrooms, Duplex town house, Pool, private OrientBeach Access
Pool
Exterior
Beach
Property grounds
Exceptional
(13 reviews)

Beachfront condo at beautiful Cupecoy Beach Club. 2 bedroom, 3 bath, amenities!

Lowlands

8% off
S$3,862
for 7 nights, 1 apartment
S$552 per night
includes taxes & fees
Beachfront condo at beautiful Cupecoy Beach Club. 2 bedroom, 3 bath, amenities!
Pool
Outdoor dining
Beach
Room
Exceptional
(21 reviews)

💖💖💖studio nature reserve pool/beach/kayak included

Cul de Sac

8% off
S$2,051
for 7 nights, 1 apartment
S$293 per night
includes taxes & fees
💖💖💖studio nature reserve pool/beach/kayak included

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

The charming area of Orient Bay awaits your stay

The beaches and other outdoor surroundings create an inviting atmosphere in Orient Bay. This romantic and relaxing city entices travellers with its restaurants and bars. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Orient Bay

Are you hoping to find top things to see and do in the area? Venture out of your holiday home and check out everything that makes Orient Bay a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mullet Bay Golf (6.9 mi / 11.2 km)
  • Aurora International Golf Club (8.8 mi / 14.2 km)

Exploring the beaches and other natural features in Orient Bay

Whether you're an adventurous traveller or just want to take in the scenery, Orient Bay is a great place to get out in nature. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Maho Beach (7.1 mi / 11.4 km)
  • Orient Bay (0.9 mi / 1.4 km)
  • Pinel Island (1.4 mi / 2.2 km)
  • Anse Marcel Beach (2.1 mi / 3.4 km)
  • Grand Case Beach (2.3 mi / 3.6 km)
  • Dawn Beach (2.7 mi / 4.3 km)

Seasonal weather averages in Orient Bay

If you're hoping to enjoy some warm-weather activities on your holiday, September, August, October and July are the hottest months to visit, when temperatures average 27°C.

Travelling to and around Orient Bay

The nearest airport is in Grand Case (SFG-L'Esperance), located 1.8 mi (2.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Philipsburg (SXM-Princess Juliana Intl.), which is 6.5 mi (10.4 km) away.

Frequently asked questions

What is the best area to stay in Orient Bay when booking a holiday rental?
Mont Vergna is one of the most sought-after neighbourhoods for a holiday home in Orient Bay. Make yourself at home here and enjoy the comfort and privacy that comes with having the whole place to yourself.
What is the most popular type of holiday rental accommodation in Orient Bay?
Villas are the most popular kind of holiday rental in Orient Bay, according to our data. Even if you have something else in mind, Vrbo has properties in all shapes and sizes. Look through our options to find your perfect match.
How much does it cost to rent a holiday rental in Orient Bay?
The average price for a holiday rental in Orient Bay depends on a number of factors, including length of stay, property type and season. Whether you're in search of a sprawling villa with space for extended family or a cosy cabin for just you and your sweetheart, just enter your travel dates to find stays with unbeatable value.
How much does it cost to rent a beach house in Orient Bay?
The average price for a holiday home by the beach in Orient Bay will depend on when you'll be there and the type and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your destination and travel dates. Then use the handy filter tool to select the number of bedrooms and amenities that you need, like air conditioning, a pool and WiFi.
Are there pet-friendly holiday rentals in Orient Bay?
Pack up a suitcase for the pooch in your life because Orient Bay has 391 holiday rentals that roll out the welcome mat to doggie guests. Let your furriest friend enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Orient Bay?
Pack your swimsuit and inflatable swan, because there are 301 houses with a private pool in Orient Bay. Settle in at one of these sought-after holiday rentals and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find a place to make a splash!
What are popular rental amenities in Orient Bay?
A swimming pool, a lake view and tennis are the most popular rental amenities in Orient Bay. Whether you plan to go alone, with your significant other or a group of family members, Vrbo can help you find a holiday home that suits your tastes with all the extras you're looking for.
Are there large group holiday rentals in Orient Bay?
With 17 holiday rentals that can host 10 or more people in Orient Bay, you don't have to keep anyone off the invite list. From fun family get-togethers to events like Christmas or New Year's Eve parties, Vrbo can help you find a large group rental to match the occasion.
Are there holiday rentals in Orient Bay that welcome kids?
Bring the whole family together for a memorable adventure in Orient Bay at one of our 386 family-friendly holiday properties. Many of these stays provide amenities that are ideal for getaways with the kids, like laundries, multiple bedrooms and entertainment units. Simply check the "Properties good for families" filter and pick your favourite.
What are the top attractions for families in Orient Bay?
Keeping the kids amused during your Orient Bay holiday is a breeze with these exciting family-friendly attractions:
  • Maho Beach
  • Mullet Bay Beach
  • Grand Case Beach
Are there one-bedroom holiday rentals in Orient Bay?
Take your pick from 145 one-bedroom rentals in Orient Bay. Whether you'd prefer a secluded cottage or a cabin, Vrbo's one-bedroom rentals are great if you don't need loads of space. One of the major perks of having your own pad? You won't need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Orient Bay?
Take off with your besties and relax in total privacy and comfort in one of the 65 two-bedroom holiday properties Orient Bay has to offer.
Are there holiday rentals with WiFi in Orient Bay?
You can pick from 178 holiday rentals with WiFi in Orient Bay. If you want to disconnect from the world during your escape, but still want to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Orient Bay?
Orient Bay has 383 holiday rentals where you'll be able to spend your days in air-conditioned comfort. To book a stay on Vrbo that provides this amenity, enter your desired travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Orient Bay?
We recommend you check with the Orient Bay holiday rental you're considering on Vrbo as the age limit varies. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Orient Bay for?
How long you can book a holiday rental in Orient Bay is down to the property. Simply enter your selected dates to display a list of options offering extended stays. With many creature comforts like air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to get a terrific place to call your home away from home in Orient Bay.

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