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, (1,296 reviews)
"Perfect location."
United States
Andre
The price is CA $200
CA $246 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Vacation Club Royal Palm St. Maarten

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 CA $169
CA $189 total
includes taxes & fees
Sep 19 - Sep 20
Simpson Bay Suites

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 CA $221
CA $381 total
includes taxes & fees
Oct 6 - Oct 7
The Hills Residence

4. 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 $416
CA $542 total
includes taxes & fees
Sep 16 - Sep 17
Turquoise paradise, directly ON beach, gated w underground parking!

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 $246 total
includes taxes & fees
Sep 16 - Sep 17
Beach Front 1 Bedroom Flat D3

6. 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 $207 total
includes taxes & fees
Sep 16 - Sep 17
Beach Front Studio C3

7. 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 $511
CA $660 total
includes taxes & fees
Sep 16 - Sep 17
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

8. C354 - Top view with balcony

C354 - Top view with balcony
Simpson Bay
The price is CA $254
CA $492 total
includes taxes & fees
Oct 4 - Oct 5
C354 - Top view with balcony

9. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is CA $144
CA $156 total
includes taxes & fees
Sep 16 - Sep 17
Blue Sail Apartments - Double room

10. 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 $295 total
includes taxes & fees
Oct 5 - Oct 6
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

11. 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 $305 total
includes taxes & fees
Sep 17 - Sep 18
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

12. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is CA $254
CA $465 total
includes taxes & fees
Sep 16 - Sep 17
D416 – Relaxing apartment with Balcony

13. 5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
The price is CA $152
CA $295 total
includes taxes & fees
Sep 17 - Sep 18
5 minutes walking from the beach 1-4B

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

15. 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 CA $160
CA $305 total
includes taxes & fees
Sep 17 - Sep 18
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

16. 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 $409
CA $551 total
includes taxes & fees
Sep 16 - Sep 17
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

17. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is CA $246
CA $263 total
includes taxes & fees
Sep 16 - Sep 17
Blue Sail Apartments - 1 bedroom apartments

18. 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 $173
CA $186 total
includes taxes & fees
Sep 16 - Sep 17
Blue Sail Apartments - Two bedroom apartments

19. 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 $971
CA $1,263 total
includes taxes & fees
Sep 16 - Sep 17
Beach Front 4 Bed Condon C2.1 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

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?

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 Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many vacation rentals are there in Simpson Bay?

With 42 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.