Book Holiday Homes in Cole Bay

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Featured Holiday Homes in Cole Bay

Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking.

Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking.

Philipsburg
Stay at this holiday home in Philipsburg. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Maho Beach and Orient Bay Beach ...
Opens in a new windowPrivate House -GreatBay- Philipsburg - Free Wifi and Free Private Parking.
LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR

LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR

Guana Bay Red Pond
Stay at this beach holiday home in Philipsburg. Enjoy private pools, breakfast (surcharge) and a fitness centre. Popular attractions Orient Bay Beach and Maho ...
Opens in a new windowLUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR
New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove

New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove

Pelican Key
Stay at this holiday home in Simpson Bay. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowNew Listing, Exceptional 3 bed & bath with private pool in Pelican Cove
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Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Simpson Bay Sint Maarten
Stay at this beach holiday home in Simpson Bay. Enjoy private pools, a beach locale and laundry facilities. Popular attractions Maho Beach and Mullet Bay Beach ...
Opens in a new windowAmazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
Novels Villa is a family-friendly home with the Caribbean Sea as your backyard.

Novels Villa is a family-friendly home with the Caribbean Sea as your backyard.

Grand-Case Collectivité de Saint-Martin
Stay at this beach holiday home in Grand Case. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Orient Bay Beach and Maho Beach are ...
Opens in a new windowNovels Villa is a family-friendly home with the Caribbean Sea as your backyard.
Villa bungalow Colibri vue sur mer et Saint Barthélémy

Villa bungalow Colibri vue sur mer et Saint Barthélémy

Cul-de-Sac Collectivity of Saint Martin
Stay at this holiday home in Orient Bay. Enjoy laundry facilities, in-room jetted baths and air conditioning. Popular attractions Orient Bay Beach and Grand ...
Opens in a new windowVilla bungalow Colibri vue sur mer et Saint Barthélémy
White Sands Retreat - Beachside at Beacon Hill

White Sands Retreat - Beachside at Beacon Hill

Beacon Hill Sint Maarten
Stay at this beach holiday home in Simpson Bay. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowWhite Sands Retreat - Beachside at Beacon Hill
Dream Beachfront Home : Stunning sea views, private pool and walking distance

Dream Beachfront Home : Stunning sea views, private pool and walking distance

Koolbaai
Stay at this holiday home in Simpson Bay. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowDream Beachfront Home : Stunning sea views, private pool and walking distance
A breath of fresh air right on the sea - relax and enjoy!

A breath of fresh air right on the sea - relax and enjoy!

2 out of 5
Sint Maarten Sint Maarten
Stay at this beach holiday home in Cole Bay. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Maho Beach and Mullet Bay Beach are located ...
Opens in a new windowA breath of fresh air right on the sea - relax and enjoy!
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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.

Cole Bay Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cole Bay vacation homes are the perfect way for you to wing it.

Holiday houses in Cole Bay let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cole Bay in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cole Bay adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cole Bay with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cole Bay vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cole Bay Holiday Homes essential information

Accommodation
249 Holiday Homes
Lowest Price
NZ$198
Highest Price
NZ$338
Popular accommodation
Private House -GreatBay- Philipsburg - Free Wifi and Free Private Parking., LUXURY VILLA! Resort Amenities, Stunning Views, Beach Access! GENERATOR, New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove, Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool , Novels Villa is a family-friendly home with the Caribbean Sea as your backyard., Villa bungalow Colibri vue sur mer et Saint Barthélémy, White Sands Retreat - Beachside at Beacon Hill, Dream Beachfront Home : Stunning sea views, private pool and walking distance , A breath of fresh air right on the sea - relax and enjoy!

Top trending hotels in Cole Bay

Port de Plaisance Resort, Trademark Collection by Wyndham

Port de Plaisance Resort, Trademark Collection by Wyndham

3.5 out of 5
155 Union Rd Cole Bay Sint Maarten
Fully refundableReserve now, pay when you stay
The price is NZ$338 per night from 11 Jan to 12 Jan
NZ$338
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this spa resort in Cole Bay. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowPort de Plaisance Resort, Trademark Collection by Wyndham
Carls Unique Inn

Carls Unique Inn

2 out of 5
18 Orange Grove Rd Cole Bay
Fully refundableReserve now, pay when you stay
The price is NZ$198 per night from 29 Dec to 30 Dec
NZ$198
29 Dec - 30 Dec
includes taxes & fees
Stay at this business-friendly hotel in Cole Bay. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowCarls Unique Inn
Diamond Gem Residence

Diamond Gem Residence

3 out of 5
Peter John Rd Cole Bay Sint Maarten
The price is NZ$199 per night from 7 Jan to 8 Jan
NZ$199
7 Jan - 8 Jan 2026
includes taxes & fees
Stay at this inn in Cole Bay. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Opens in a new windowDiamond Gem Residence
Save an average of 15% on thousands of hotels when you're signed in
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
Stay at this spa resort in Simpson Bay. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the pool and the restaurant in their reviews. ...
Opens in a new windowThe Morgan Resort Spa Village
Don't see what you're looking for?
See all available properties in Cole Bay
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.