A wooden pier extending into calm waters with sailboats anchored nearby.

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Our top choices for Simpson Bay holiday rentals

1. Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,264 reviews)
"It was a great stay"
United States
Shawn
The price is £137
includes taxes & fees
25 Aug - 26 Aug
Hilton Vacation Club Royal Palm St. Maarten

2. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (161 reviews)
"AC worked well the room was cleaned daily and the staff was always friendly and made great suggestions for dinning and places to see."
United States
Michael
The price is £101
includes taxes & fees
10 Aug - 11 Aug
Simpson Bay Suites

3. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (162 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is £191
includes taxes & fees
19 Aug - 20 Aug
The Hills Residence

4. Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 reviews)
"Really cool place and the location was prime. The cleaning lady was the nicest person there could be as well. "
Canada
Benjamin
The price is £121
includes taxes & fees
10 Aug - 11 Aug
Beach Front Studio C3

5. Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (3 reviews)
"Great location near Simpson Bay restaurants and nightlife. Accommodations were exactly as pictured with modern furnishings. Car rental is recommended to fully enjoy the island. "
United States
Christopher
The price is £143
includes taxes & fees
10 Aug - 11 Aug
Beach Front 1 Bedroom Flat D3

6. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is £96
includes taxes & fees
10 Aug - 11 Aug
Blue Sail Apartments - Double room

7. Modern apartment with shared pool and generator (2-2B)

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
The price is £168
includes taxes & fees
10 Aug - 11 Aug
Modern apartment with shared pool and generator (2-2B)

8. 1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
"perfect!!"
United States
jason l.
The price is £164
includes taxes & fees
12 Aug - 13 Aug
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

9. Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Simpson Bay
The price is £168
includes taxes & fees
10 Aug - 11 Aug
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

10. C354 - Top view with balcony

C354 - Top view with balcony
Simpson Bay
The price is £277
includes taxes & fees
16 Aug - 17 Aug
C354 - Top view with balcony

11. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
C344 - Lagoon view with balcony

12. Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Simpson Bay
8.6 out of 10, Excellent, (7 reviews)
"Great place to stay with a lot of privacy and walkable to stores and restaurants. Amazing views! Lisa is so friendly and keeps the place amazing!"
United States
Alaciel S.
The price is £344
includes taxes & fees
15 Aug - 16 Aug
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

13. B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
The price is £267
includes taxes & fees
10 Aug - 11 Aug
B225 - Incredible Lagoon View

14. Turquoise paradise, directly ON beach, gated w underground parking!

Turquoise paradise, directly ON beach, gated w underground parking!
Simpson Bay
9.8 out of 10, Exceptional, (22 reviews)
"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 £395
includes taxes & fees
10 Aug - 11 Aug
Turquoise paradise, directly ON beach, gated w underground parking!

15. B245 - Condo with amazing view

B245 - Condo with amazing view
Sint Maarten
B245 - Condo with amazing view

16. B204 - Amazing 1 Bedroom with terrace

B204 - Amazing 1 Bedroom with terrace
Sint Maarten
The price is £277
includes taxes & fees
11 Aug - 12 Aug
B204 - Amazing 1 Bedroom with terrace

17. C314 - Stunning 1 Bedroom Apartment

C314 - Stunning 1 Bedroom Apartment
Sint Maarten
The price is £264
includes taxes & fees
10 Aug - 11 Aug
C314 - Stunning 1 Bedroom Apartment

18. A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
A116 - Immersive Simpson Bay Lagoon View

19. Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Perfect location for us! We wanted easy access to see the planes coming in and it could not have been more perfect. Close to taxis and buses. Hosts were excellent at communicating. Friendly staff, would recommend!! "
United States
Laura
Maho Beach House Ocean Front Garden Studio

20. A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
The price is £275
includes taxes & fees
9 Sept - 10 Sept
A101 - Outstanding Lagoon View & Garden
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, apart-hotels, 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 £101 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?

New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove: This highly rated holiday home rental in Simpson Bay offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and White Sands Retreat - Beachside at Beacon Hill.

How many holiday rentals are there in Simpson Bay?

With 46 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. In the wider area, you’ll find popular places such as Maho Beach and Mullet Bay Beach.

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.