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

Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Simpson Bay vacation rentals

On the beach, sun loungers, beach umbrellas, beach towels

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, (1,268 reviews)
"It was a great stay"
United States
Shawn
The price is SAR 508
SAR 632 total
includes taxes & fees
25 Aug - 26 Aug
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony

2. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very Good, (164 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is SAR 591
SAR 1,024 total
includes taxes & fees
23 Aug - 24 Aug
The Hills Residence
Terrace/patio

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 SAR 456
SAR 511 total
includes taxes & fees
19 Aug - 20 Aug
Simpson Bay Suites
Beach

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 SAR 372
SAR 597 total
includes taxes & fees
16 Aug - 17 Aug
Beach Front Studio C3
Beach

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 SAR 470
SAR 710 total
includes taxes & fees
20 Aug - 21 Aug
Beach Front 1 Bedroom Flat D3
Pool

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 SAR 410
SAR 814 total
includes taxes & fees
17 Aug - 18 Aug
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Property grounds

7. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is SAR 391
SAR 469 total
includes taxes & fees
16 Aug - 17 Aug
Blue Sail Apartments - Double room
Pool

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)
Pool

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 SAR 432
SAR 836 total
includes taxes & fees
20 Aug - 21 Aug
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Property grounds

10. C354 - Top view with balcony

C354 - Top view with balcony
Simpson Bay
The price is SAR 731
SAR 1,390 total
includes taxes & fees
16 Aug - 17 Aug
C354 - Top view with balcony
TV

11. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is SAR 687
SAR 1,334 total
includes taxes & fees
5 Sep - 6 Sep
D416 – Relaxing apartment with Balcony
Pool

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 SAR 1,105
SAR 1,582 total
includes taxes & fees
16 Aug - 17 Aug
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Interior

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 SAR 653
SAR 939 total
includes taxes & fees
18 Aug - 19 Aug
Maho Beach Escape; Sunset Ocean View
Pool

14. B245 - Condo with amazing view

B245 - Condo with amazing view
Sint Maarten
The price is SAR 687
SAR 1,334 total
includes taxes & fees
20 Aug - 21 Aug
B245 - Condo with amazing view
Property grounds

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 SAR 1,483
SAR 1,971 total
includes taxes & fees
16 Aug - 17 Aug
Turquoise paradise, directly ON beach, gated w underground parking!
A heated pool

16. C314 - Stunning 1 Bedroom Apartment

C314 - Stunning 1 Bedroom Apartment
Sint Maarten
The price is SAR 731
SAR 1,324 total
includes taxes & fees
19 Aug - 20 Aug
C314 - Stunning 1 Bedroom Apartment
Living area

17. D442 - Apartment with balcony and lagoon view

D442 - Apartment with balcony and lagoon view
Cole Bay
The price is SAR 731
SAR 1,390 total
includes taxes & fees
19 Aug - 20 Aug
D442 - Apartment with balcony and lagoon view
A heated pool

18. A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
The price is SAR 731
SAR 1,386 total
includes taxes & fees
9 Sep - 10 Sep
A101 - Outstanding Lagoon View & Garden
Outdoor dining

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 SAR 469
SAR 547 total
includes taxes & fees
16 Aug - 17 Aug
Blue Sail Apartments - Two bedroom apartments
Pool

20. A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
The price is SAR 731
SAR 1,390 total
includes taxes & fees
20 Aug - 21 Aug
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

La Vista Hotel

La Vista Hotel

10/10 Excellent
"Very clean, quiet, but still close enough gh to everything."
Brian M 5-night trip
Posted 1 hour ago
La Vista Hotel

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 45 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.