Photo by Dino Russo

Cole Bay holiday homes

We found 3,165 holiday rentals — enter your dates for availability

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April 2025

May 2025

Discover a selection of 30 apartments, 31 villas and other holiday rentals in Cole Bay that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a pool. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Cole Bay

Showing deals for:18/07/2025 - 25/07/2025

large terrace and lounge with Wonderfull sea view on Orient Beach

9.8/10Exceptional (36 reviews)

3 BERDOOMS VILLA WITH AN OPEN SEA VIEW FROM ORIENT BEACH TO PINEL ISLAND

Cul de Sac, -

8% off

NZ$1,167 per night

includes taxes & fees

9.2/10Wonderful (9 reviews)

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (A)

Philipsburg, SX

8% off

NZ$1,838 per night

includes taxes & fees

10/10Exceptional (21 reviews)

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (H)

Philipsburg, Sint Maarten

8% off

NZ$1,914 per night

includes taxes & fees

10/10Exceptional (15 reviews)

DISCOUNTED RATE for a renovated 3 bedroom villa - VILLA HARMONY - Terres Basses

Nettle Bay, Collectivité de Saint-Martin

9% off

NZ$1,316 per night

includes taxes & fees

The Boardwalk is less than a 5 minute walk...

9.8/10Exceptional (10 reviews)

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

Philipsburg

22% off

NZ$187 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cole Bay

Dining with beautiful seaview
Repas avec vue sur mer

Villa Olisa, dream villa with a breathtaking view and private pool.

Sleeps 6 · 3 bedrooms · 3 bathrooms

Very private villa with awesome views overlooking Simpson Bay and Full Generator

Sleeps 10 · 5 bedrooms · 5 bathrooms

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

Sleeps 7 · 3 bedrooms · 2+ bathrooms

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Delight in the beachside landscape of Cole Bay

The beaches and other outdoor surroundings create an inviting atmosphere in Cole Bay. This romantic and scenic city entices travellers with its restaurants and boating. Maho Beach and Orient Bay Beach are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Cole Bay

Are you hoping to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Cole Bay a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Mullet Bay Golf (2.5 mi / 4 km)
Aurora International Golf Club (9.9 mi / 15.9 km)

Exploring the natural landscape of Cole Bay

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Cole Bay is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

Maho Beach (2.5 mi / 4 km)
Orient Bay Beach (5.3 mi / 8.5 km)
Flamingo Beach (1.2 mi / 1.9 km)
Simpson Bay Beach (1.9 mi / 3.1 km)
Little Bay Beach (2.1 mi / 3.3 km)
Great Bay Beach (2.1 mi / 3.4 km)

How to get to and around Cole Bay

The nearest airport is in Philipsburg (SXM-Princess Juliana Intl.), located 2 mi (3.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Grand Case (SFG-L'Esperance), which is 4.8 mi (7.8 km) away.

Frequently asked questions

What is the best area to stay in Cole Bay when booking a holiday home?

Almond Grove is among the more desired neighbourhoods for a holiday property in Cole Bay. Spend your time here to enjoy all the privacy and comfort that comes with having a whole place to yourself.

What is the most popular type of holiday home accommodation in Cole Bay?

Based on our data, villas are the most sought-after type of property in Cole Bay. But of course, everyone’s idea of an awesome trip differs. Bookabach has holiday homes of all sizes, shapes and budgets, and we’ll help you locate your ideal match.

How much does it cost to rent a holiday home in Cole Bay?

Season, property type and length of stay are some factors that can affect the price of a holiday home. Simply add your travel dates to find your ideal fit. From comfy cottages to sprawling villas, all Bookabach holiday homes provide amazing value.

How much does it cost to rent a beach house in Cole Bay?

When you travel and the style and size of the property will determine the cost of your beachside escape. Click on your Cole Bay travel dates to see your options on Bookabach. Can’t live without a private pool? Use our filters to choose the features and amenities you need.

Are there pet-friendly holiday homes in Cole Bay?

There are, yes. Take your pick of 54 holiday homes that roll out the welcome mat in Cole Bay on Bookabach. Our cuddly best friends also deserve a little time out, so simply use our search function for pet-friendly holiday homes to book a pad where Spot can join the fun.

Can I rent a house with a pool in Cole Bay?

Pack your swimming gear and inflatable lounger, because there are 41 houses with a private pool in Cole Bay. Unwind at one of these sought-after holiday homes and let every day be a pool day. Simply enter your dates into Bookabach, then check the “pool” filter to find the ideal place for a splashing good time!

What are popular home amenities in Cole Bay?

A chef, an ocean view and a firepit top the list of most popular home amenities in Cole Bay. Whether you plan to travel alone, with your sweetheart or a bunch of friends, Bookabach can help you find a holiday home that matches your style with a load of extras you’ll love.

Are there large group holiday homes in Cole Bay?

Yes, you’ll find 24 holiday homes in Cole Bay that can accommodate five or more guests. From family get-togethers to events like a friend’s birthday, these stays have ample room to spend time with the people you love.

Are there holiday homes in Cole Bay that welcome kids?

Cole Bay has 54 family-friendly holiday homes to choose from. And discovering a stay that welcomes children is a cinch with Bookabach’s “Properties good for families” filter. As well as having the entire place to yourselves, you’ll get perks and conveniences like extra bedrooms, kitchens and pools.

What are the top attractions for families in Cole Bay?

There’s a ton of cool things to see and do with the family in Cole Bay, such as:

Maho Beach
Mullet Bay Beach
Grand Case Beach

Are there one-bedroom holiday homes in Cole Bay?

You’ll find 12 one-bedroom properties in Cole Bay to choose from. A one-bedroom holiday property is a superb choice if it’s just you and your partner or if you’re flying solo. Add in more convenience, privacy and space compared to a hotel, and you’re bound to have an unforgettable break.

Can I find two-bedroom holiday homes in Cole Bay?

You can pick from 14 two-bedroom holiday properties in Cole Bay. Give the kids the second room or fill it with a couple of your nearest and dearest friends. There’s ample space for whoever’s fortunate enough to come along for the ride.

Are there holiday homes with WiFi in Cole Bay?

Whether you want to keep up with the headlines, write a few emails or surf social media, there are 19 holiday homes with WiFi in Cole Bay. Check the “WiFi” box when searching on Bookabach and stay connected on your holiday.

How can I find holiday homes with air conditioning in Cole Bay?

Cole Bay has 52 holiday homes where you can chill out in air-conditioned comfort. To book a stay on Bookabach offering this perk, choose your travel dates and use the handy filter tool to select the “air conditioning” box.

How old do you have to be to rent a holiday home in Cole Bay?

The minimum age permitted can differ between properties on Bookabach, so look at the rules of the holiday home in Cole Bay you’re considering. But in general, it’s 16, 18 or 21.

How long can I rent a holiday home in Cole Bay for?

The amount of time you can stay in a Cole Bay holiday home for depends on the property. Just tap in your dates of travel to see options that offer extended stays. They feature everything you need to make your extended holiday more comfortable and convenient, like kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounted prices, so you can have a longer stay for less.