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

Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation 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, (1,267 reviews)
"It was a great stay"
United States
Shawn
The price is CA $188
CA $234 total
includes taxes & fees
Aug 25 - Aug 26
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, (163 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is CA $219
CA $380 total
includes taxes & fees
Aug 17 - Aug 18
The Hills Residence

3. 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 CA $169
CA $189 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $138
CA $221 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $174
CA $259 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $152
CA $296 total
includes taxes & fees
Aug 19 - Aug 20
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 CA $145
CA $174 total
includes taxes & fees
Aug 24 - Aug 25
Blue Sail Apartments - Double room

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

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
Modern apartment with shared pool and generator (2-2B)

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 CA $160
CA $306 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $271
CA $511 total
includes taxes & fees
Aug 20 - Aug 21
C354 - Top view with balcony

11. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is CA $255
CA $490 total
includes taxes & fees
Sep 9 - Sep 10
D416 – Relaxing apartment 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
8.8 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 CA $461
CA $643 total
includes taxes & fees
Aug 19 - Aug 20
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

13. 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 CA $217
CA $318 total
includes taxes & fees
Aug 13 - Aug 14
Maho Beach Escape; Sunset Ocean View

14. B245 - Condo with amazing view

B245 - Condo with amazing view
Sint Maarten
The price is CA $255
CA $494 total
includes taxes & fees
Aug 15 - Aug 16
B245 - Condo with amazing view

15. 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 CA $550
CA $729 total
includes taxes & fees
Aug 19 - Aug 20
Turquoise paradise, directly ON beach, gated w underground parking!

16. C314 - Stunning 1 Bedroom Apartment

C314 - Stunning 1 Bedroom Apartment
Sint Maarten
The price is CA $271
CA $490 total
includes taxes & fees
Aug 14 - Aug 15
C314 - Stunning 1 Bedroom Apartment

17. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
The price is CA $271
CA $515 total
includes taxes & fees
Aug 14 - Aug 15
D442 - Apartment with balcony and lagoon view

18. A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
The price is CA $312
CA $561 total
includes taxes & fees
Aug 25 - Aug 26
A101 - Outstanding Lagoon View & Garden

19. 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 CA $174
CA $202 total
includes taxes & fees
Aug 19 - Aug 20
Blue Sail Apartments - Two bedroom apartments

20. A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
The price is CA $271
CA $511 total
includes taxes & fees
Aug 20 - Aug 21
A116 - Immersive Simpson Bay 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Simpson Bay?

Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to 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 vacation home rentals that Simpson Bay has to offer?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. Other favorite homes for rent in Simpson Bay are New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and White Sands Retreat - Beachside at Beacon Hill.

How many vacation rentals are there in Simpson Bay?

With 46 Expedia vacation rentals, you're sure 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 vacation rental in Simpson Bay like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.