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

Simpson Bay Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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, (1,263 reviews)
"It was a great stay"
United States
Shawn
The price is AED 555
AED 680 total
includes taxes & fees
25 Aug - 26 Aug
Hilton Vacation Club Royal Palm St. Maarten
Terrace/patio

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 AED 446
AED 500 total
includes taxes & fees
7 Aug - 8 Aug
Simpson Bay Suites
Amazing Top Floor Apartment | Balcony

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 AED 582
AED 978 total
includes taxes & fees
19 Aug - 20 Aug
The Hills Residence
Beach

4. 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 AED 511
AED 753 total
includes taxes & fees
3 Sep - 4 Sep
Beach Front 1 Bedroom Flat D3
Beach

5. 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 AED 364
AED 584 total
includes taxes & fees
3 Sep - 4 Sep
Beach Front Studio C3
Property grounds

6. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is AED 382
AED 458 total
includes taxes & fees
12 Aug - 13 Aug
Blue Sail Apartments - Double room
Pool

7. 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 AED 401
AED 785 total
includes taxes & fees
4 Sep - 5 Sep
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Pool

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 AED 422
AED 811 total
includes taxes & fees
4 Sep - 5 Sep
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Pool

9. C352 - Top view with balcony

C352 - Top view with balcony
Simpson Bay
C352 - Top view with balcony
Pool

10. 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 AED 1,081
AED 1,551 total
includes taxes & fees
8 Aug - 9 Aug
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Property grounds

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 AED 1,451
AED 1,932 total
includes taxes & fees
7 Aug - 8 Aug
Turquoise paradise, directly ON beach, gated w underground parking!
TV

12. B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
B225 - Incredible Lagoon View
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 AED 661
AED 944 total
includes taxes & fees
9 Aug - 10 Aug
Maho Beach Escape; Sunset Ocean View
Interior

14. D428 – Spacious 2-Bedroom Lagoon View with Balcony

D428 – Spacious 2-Bedroom Lagoon View with Balcony
Sint Maarten
7.0 out of 10, Good, (2 reviews)
"The location, view and hotel were very beautiful. But getting towels was extremely difficult, the home was not equipped with things like dustpan, bowls and things. I would stay again but I recommend an easier way of contacting the front desk for necessities. "
United Kingdom
Kaylin W.
D428 – Spacious 2-Bedroom Lagoon View with Balcony
Interior

15. Maho Beach Suite

Maho Beach Suite
Simpson Bay
Maho Beach Suite
Outdoor dining

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 AED 457
AED 534 total
includes taxes & fees
7 Aug - 8 Aug
Blue Sail Apartments - Two bedroom apartments
Outdoor dining

17. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is AED 648
AED 741 total
includes taxes & fees
13 Aug - 14 Aug
Blue Sail Apartments - 1 bedroom apartments
TV

18. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is AED 672
AED 1,305 total
includes taxes & fees
4 Sep - 5 Sep
D416 – Relaxing apartment with Balcony
TV

19. D434 - Amazing Apartment with Balcony

D434 - Amazing Apartment with Balcony
Sint Maarten
The price is AED 672
AED 1,305 total
includes taxes & fees
4 Sep - 5 Sep
D434 - Amazing Apartment with Balcony
Pool

20. D406 - Incredible Apartment With Terrace

D406 - Incredible Apartment With Terrace
Cole Bay
The price is AED 672
AED 1,305 total
includes taxes & fees
4 Sep - 5 Sep
D406 - Incredible Apartment With Terrace
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"Very Nice overall"
Claudia 6-night trip
Posted less than an hour ago
Simpson Bay Resort, Marina & Spa

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 lively bars and top-notch restaurants.

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

New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove: Visitors like this Simpson Bay vacation home rental. It 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 you can cook with friends or family. Other favorite 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 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. In the larger area, you’ll find popular places like Maho Beach and Mullet Bay Beach.

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.