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, (1,310 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is NZ$252
includes taxes & fees
11 Oct - 12 Oct
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, (166 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is NZ$269
includes taxes & fees
6 Oct - 7 Oct
Simpson Bay Suites

3. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
The price is NZ$507
includes taxes & fees
6 Oct - 7 Oct
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 NZ$283
includes taxes & fees
6 Oct - 7 Oct
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 NZ$331
includes taxes & fees
6 Oct - 7 Oct
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 NZ$216
includes taxes & fees
6 Oct - 7 Oct
Blue Sail Apartments - Double room

7. 5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
The price is NZ$379
includes taxes & fees
6 Oct - 7 Oct
5 minutes walking from the beach 1-4B

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 NZ$391
includes taxes & fees
6 Oct - 7 Oct
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

9. 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.
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

10. 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 NZ$391
includes taxes & fees
6 Oct - 7 Oct
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

11. C354 - Top view with balcony

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

12. Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
"Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating."
United States
Colleen M.
The price is NZ$431
includes taxes & fees
2 Nov - 3 Nov
Maho Beach House: Studio Getaway, Oceanfront Vibe

13. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is NZ$615
includes taxes & fees
6 Oct - 7 Oct
C344 - Lagoon view with balcony

14. 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 NZ$743
includes taxes & fees
6 Oct - 7 Oct
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

15. D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
D407 – Charming Apartment with Terrace

16. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
D402 - Beautiful apartment with garden and view

17. A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
A101 - Outstanding Lagoon View & Garden

18. B231 - Serene Chic 2 Bedroom

B231 - Serene Chic 2 Bedroom
Sint Maarten
B231 - Serene Chic 2 Bedroom

19. D438 – Amazing 2-Bedroom Lagoon View with Balcony

D438 – Amazing 2-Bedroom Lagoon View with Balcony
Sint Maarten
8.0 out of 10, Very good, (1 review)
"Clean room, amazing view!! A little precarious getting up there though- should have more of a description of the challenge of getting to the unit!"
United States
ALLEN
D438 – Amazing 2-Bedroom Lagoon View with Balcony

20. Utopia A3 | Beachside Stay @ The Drake Residences

Utopia A3 | Beachside Stay @ The Drake Residences
Simpson Bay
The price is NZ$1,380
includes taxes & fees
6 Oct - 7 Oct
Utopia A3 | Beachside Stay @ The Drake Residences
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Simpson Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Simpson Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Simpson Bay. Seeing all the best attractions is bound to make you fall in love with Simpson Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Simpson Bay short-term rentals, that won’t be hard to do.

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?

Philips Scott House Calinago: This holiday home rental outside of Simpson Bay is in a shopping district, and equipped with air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities such as a microwave and free parking are also available for your convenience. Another good choice for your trip to Simpson Bay is Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many holiday rentals are there in Simpson Bay?

With 38 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. Hollywood Casino and Simpson Bay Beach 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.