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, (1,262 reviews)
"Rooms were clean and staff were great"
United States
Rosaida
The price is CA $212
CA $259 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, (160 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is CA $223
CA $384 total
includes taxes & fees
Aug 27 - Aug 28
The Hills Residence

3. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (160 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 $170
CA $191 total
includes taxes & fees
Aug 2 - Aug 3
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 $139
CA $223 total
includes taxes & fees
Aug 5 - Aug 6
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 $175
CA $261 total
includes taxes & fees
Aug 2 - Aug 3
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 CA $145
CA $174 total
includes taxes & fees
Aug 1 - Aug 2
Blue Sail Apartments - Double room

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 CA $153
CA $299 total
includes taxes & fees
Aug 2 - Aug 3
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

8. 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 CA $412
CA $592 total
includes taxes & fees
Aug 3 - Aug 4
Beach Front 2 Bed Condon C1.1 with Sea View and Private 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 CA $161
CA $309 total
includes taxes & fees
Aug 3 - Aug 4
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

10. Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
Maho Beach House - Petit Studio Océanique - Charmante Vue

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 CA $553
CA $737 total
includes taxes & fees
Aug 2 - Aug 3
Turquoise paradise, directly ON beach, gated w underground parking!

12. B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
The price is CA $256
CA $499 total
includes taxes & fees
Aug 3 - Aug 4
B225 - Incredible Lagoon View

13. Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is CA $472
CA $660 total
includes taxes & fees
Aug 25 - Aug 26
Maho Beach Suite

14. 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 $203 total
includes taxes & fees
Aug 5 - Aug 6
Blue Sail Apartments - Two bedroom apartments

15. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is CA $246
CA $279 total
includes taxes & fees
Aug 1 - Aug 2
Blue Sail Apartments - 1 bedroom apartments

16. 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 CA $515
CA $706 total
includes taxes & fees
Aug 4 - Aug 5
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

17. 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 $253
CA $359 total
includes taxes & fees
Aug 1 - Aug 2
Maho Beach Escape; Sunset Ocean View

18. Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!

Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
Simpson Bay
10.0 out of 10, Exceptional, (4 reviews)
"Location worked out well close to airport. We were able to walk to beach and restaurants "
United States
Dominick C.
The price is CA $933
CA $1,288 total
includes taxes & fees
Aug 3 - Aug 4
Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!

19. Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!

Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!
Simpson Bay
2.0 out of 10, (1 review)
The price is CA $933
CA $1,288 total
includes taxes & fees
Aug 9 - Aug 10
Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!

20. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (250 reviews)
"Great stay"
United States
Drunisha
The price is CA $128
CA $134 total
includes taxes & fees
Aug 12 - Aug 13
July Apartments
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 lively bars and top-notch restaurants.

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

Philips Scott House Calinago: This vacation home rental outside 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. Some other homes for rent in Simpson Bay include New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

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. 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.