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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (1,304 reviews)
"Perfect location."
United States
Andre
The price is AED 528
AED 650 total
includes taxes & fees
4 Oct - 5 Oct
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, (165 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is AED 446
AED 500 total
includes taxes & fees
22 Sep - 23 Sep
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, (169 reviews)
"Very good"
United States
Alyssia
The price is AED 566
AED 989 total
includes taxes & fees
4 Oct - 5 Oct
The Hills Residence
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 AED 364
AED 584 total
includes taxes & fees
22 Sep - 23 Sep
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 AED 511
AED 753 total
includes taxes & fees
22 Oct - 23 Oct
Beach Front 1 Bedroom Flat D3
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 380
AED 456 total
includes taxes & fees
22 Sep - 23 Sep
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 796 total
includes taxes & fees
5 Oct - 6 Oct
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Pool

8. 5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
The price is AED 401
AED 796 total
includes taxes & fees
22 Sep - 23 Sep
5 minutes walking from the beach 1-4B
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 AED 422
AED 785 total
includes taxes & fees
25 Sep - 26 Sep
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Property grounds

10. 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 1,098
AED 1,528 total
includes taxes & fees
22 Sep - 23 Sep
Turquoise paradise, directly ON beach, gated w underground parking!
Pool

11. 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 AED 1,081
AED 1,551 total
includes taxes & fees
22 Sep - 23 Sep
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Interior

12. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
The price is AED 672
AED 1,309 total
includes taxes & fees
6 Oct - 7 Oct
C344 - Lagoon view with balcony
TV

13. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is AED 672
AED 1,309 total
includes taxes & fees
3 Oct - 4 Oct
D416 – Relaxing apartment with Balcony
Beach

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 AED 422
AED 818 total
includes taxes & fees
19 Oct - 20 Oct
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)
Outdoor dining

15. 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 456
AED 532 total
includes taxes & fees
22 Sep - 23 Sep
Blue Sail Apartments - Two bedroom apartments
Outdoor dining

16. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is AED 645
AED 738 total
includes taxes & fees
22 Sep - 23 Sep
Blue Sail Apartments - 1 bedroom apartments
Interior

17. D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
The price is AED 672
AED 1,309 total
includes taxes & fees
22 Sep - 23 Sep
D407 – Charming Apartment with Terrace
TV

18. D434 - Amazing Apartment with Balcony

D434 - Amazing Apartment with Balcony
Sint Maarten
D434 - Amazing Apartment with Balcony
Pool

19. D406 - Incredible Apartment With Terrace

D406 - Incredible Apartment With Terrace
Cole Bay
The price is AED 672
AED 1,309 total
includes taxes & fees
22 Sep - 23 Sep
D406 - Incredible Apartment With Terrace
Pool

20. Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Incredible property. Views for days, great location. Had a wonderful stay and Lisa was great also. Very secure condo and clean. Loved the pool and so many dining options close by. "
United States
Camelo
The price is AED 1,352
AED 1,859 total
includes taxes & fees
22 Sep - 23 Sep
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
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

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

10/10 Excellent
"The staff was amazing! They made our stay very welcoming and accommodating."
Chanel 2-night trip
Posted 1 hour ago
Hilton Vacation Club Royal Palm St. Maarten

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?

Philips Scott House Calinago: This vacation 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 like 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 vacation rentals are there in Simpson Bay?

With 37 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. Hollywood Casino and Simpson Bay Beach 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.