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

Simpson Bay Holiday Rentals

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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, (1,275 reviews)
"It was a great stay"
United States
Shawn
The price is AU$235
includes taxes & fees
19 Sept - 20 Sept
Hilton Vacation Club Royal Palm St. Maarten

2. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (167 reviews)
"View"
United States
Enuska
The price is AU$374
includes taxes & fees
3 Sept - 4 Sept
The Hills Residence

3. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (163 reviews)
"It was good value for money."
United States
Tirichmir
The price is AU$190
includes taxes & fees
31 Aug - 1 Sept
Simpson Bay Suites

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 AU$225
includes taxes & fees
31 Aug - 1 Sept
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 AU$264
includes taxes & fees
31 Aug - 1 Sept
Beach Front 1 Bedroom Flat D3

6. 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 AU$302
includes taxes & fees
2 Sept - 3 Sept
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

7. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is AU$178
includes taxes & fees
31 Aug - 1 Sept
Blue Sail Apartments - Double room

8. 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 AU$309
includes taxes & fees
13 Sept - 14 Sept
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

9. 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
8.8 out of 10, Excellent, (8 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 AU$572
includes taxes & fees
31 Aug - 1 Sept
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

10. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is AU$480
includes taxes & fees
10 Sept - 11 Sept
C344 - Lagoon view with balcony

11. 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 AU$728
includes taxes & fees
31 Aug - 1 Sept
Turquoise paradise, directly ON beach, gated w underground parking!

12. B243 - Deluxe 1 Bedroom

B243 - Deluxe 1 Bedroom
Sint Maarten
The price is AU$488
includes taxes & fees
31 Aug - 1 Sept
B243 - Deluxe 1 Bedroom

13. D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
The price is AU$488
includes taxes & fees
1 Sept - 2 Sept
D407 – Charming Apartment with Terrace

14. The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Simpson Bay
The price is AU$312
includes taxes & fees
31 Aug - 1 Sept
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

15. Maho Beach Escape; Sunset Ocean View

Maho Beach Escape; Sunset Ocean View
Maho, Sint Maarten
10.0 out of 10, Exceptional, (4 reviews)
"Self check in and out was a nice experience "
United States
Kelva
The price is AU$327
includes taxes & fees
31 Aug - 1 Sept
Maho Beach Escape; Sunset Ocean View

16. Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is AU$207
includes taxes & fees
31 Aug - 1 Sept
Blue Sail Apartments - Two bedroom apartments

17. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is AU$281
includes taxes & fees
13 Sept - 14 Sept
Blue Sail Apartments - 1 bedroom apartments

18. C322 - Beautiful 1-Bedroom Unit with Balcony

C322 - Beautiful 1-Bedroom Unit with Balcony
Sint Maarten
C322 - Beautiful 1-Bedroom Unit with Balcony

19. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is AU$488
includes taxes & fees
5 Sept - 6 Sept
D416 – Relaxing apartment with Balcony

20. B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
B225 - Incredible Lagoon View
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 favourite 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 depend 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 AU$126 per night. Entering your travel dates in the search wizard might find you 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 top-notch restaurants and lively bars.

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

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : This highly rated holiday home rental in Simpson Bay is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Simpson Bay is New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many holiday rentals are there in Simpson Bay?

With 43 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.