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Simpson Bay Holiday Rentals

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Our top choices for Simpson Bay holiday rentals

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.8 out of 10, Excellent, (62)
"Good location, walkable area, great views. "
United States
Tiffany
The Hills Residence

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
7.0 out of 10, Good, (127)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
The price is NZ$326
includes taxes & fees
2 Jan - 3 Jan 2026
Simpson Bay Suites
4.0 star property
9.0 out of 10, Wonderful, (1167)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is NZ$738
includes taxes & fees
6 Jan - 7 Jan 2026
Hilton Vacation Club Royal Palm St. Maarten
10.0 out of 10, Exceptional, (2)
"perfect!!"
United States
jason l.
The price is NZ$548
includes taxes & fees
13 Jan - 14 Jan 2026
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
2.0 star property
The price is NZ$621
includes taxes & fees
5 Jan - 6 Jan 2026
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Apartment in Sint Maarten

C337 - Charming 2-Bedroom Lagoon View
2.0 star property
C337 - Charming 2-Bedroom Lagoon View
9.4 out of 10, Exceptional, (3)
"The Maho was very clean, quiet and close to the airport. I recommend for people passing through or for a few days on St. Martins."
United States
David V.
The price is NZ$572
includes taxes & fees
29 Jan - 30 Jan 2026
Maho Beach Modern 1-Bedroom, Ocean Level
10.0 out of 10, Exceptional, (1)
"We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful."
United States
Trish S.
The price is NZ$885
includes taxes & fees
21 Jan - 22 Jan 2026
Marina Views in the Heart of Simpson Bay
2.0 star property
The price is NZ$651
includes taxes & fees
7 Jan - 8 Jan 2026
D426 - Beautiful view of the lagoon with balcony
2.0 star property
C331 - Beautiful Condo with Lagoon Views
2.0 star property
The price is NZ$624
includes taxes & fees
9 Jan - 10 Jan 2026
C302 – Modern Comfort with Private Terrace
2.0 star property
D408 – Chic & Stylish 2 Bedroom with Terrace

Apartment in Sint Maarten

C334 - Cozy Apartment with balcony
2.0 star property
The price is NZ$638
includes taxes & fees
7 Jan - 8 Jan 2026
C334 - Cozy Apartment with balcony
9.0 out of 10, Wonderful, (2)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
The price is NZ$690
includes taxes & fees
1 Jan - 2 Jan 2026
Maho Beach House - Petit Studio Océanique - Charmante Vue
9.8 out of 10, Exceptional, (20)
"This is the perfect place to stay location wise and with the beach views! Also there is a/c in each room which is super nice! "
United States
Rachel S.
The price is NZ$1,281
includes taxes & fees
13 Jan - 14 Jan 2026
Turquoise paradise, directly ON beach, gated w underground parking!

Apartment in Sint Maarten

D434 - Amazing Apartment with Balcony
D434 - Amazing Apartment with Balcony
9.4 out of 10, Exceptional, (16)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
The price is NZ$895
includes taxes & fees
26 Jan - 27 Jan 2026
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
The price is NZ$635
includes taxes & fees
21 Jan - 22 Jan 2026
A116 - Immersive Simpson Bay Lagoon View

Apartment in Sint Maarten

A102 - Cozy Apartment with Garden
The price is NZ$623
includes taxes & fees
13 Jan - 14 Jan 2026
A102 - Cozy Apartment with Garden

Apartment in Simpson Bay

C354 - Top view with balcony
C354 - Top view with balcony
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 Simpson Bay Hotel Reviews

Find out more about Simpson Bay

Everything you need to know about Simpson Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simpson Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay holiday rentals we have selected for you start as low as NZ$326 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the lively bars and top-notch restaurants.

What are some of the best holiday rentals that Simpson Bay has to offer?

Caribbean Sea Studio next to The Morgan Resort: This highly rated holiday home rental in Simpson Bay is located on the beach, and has an outdoor pool, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and 1 hot tub. Other favourite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Charming 3BR Villa w Private Pool in Pelican Key.

How many holiday rentals are there in Simpson Bay?

With 41 Expedia holiday rentals, you're guaranteed to find just the right place for your Simpson Bay stay.

What’s there to see and do in Simpson Bay?

Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. Simpson Bay Beach and Hollywood Casino are other places to visit while you're in town.

What’s a holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.