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

Simpson Bay Holiday Rentals

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Our top choices for Simpson Bay holiday 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, (1,319 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is AU$279
includes taxes & fees
5 Nov - 6 Nov
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, (171 reviews)
"Very good"
United States
Alyssia
The price is AU$394
includes taxes & fees
22 Oct - 23 Oct
The Hills Residence

3. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (168 reviews)
"Overall good. Location is great."
Canada
Manishkumar
The price is AU$217
includes taxes & fees
16 Oct - 17 Oct
Simpson Bay Suites

4. 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 AU$205
includes taxes & fees
16 Oct - 17 Oct
Blue Sail Apartments - Two bedroom apartments

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 AU$231
includes taxes & fees
16 Oct - 17 Oct
Beach Front Studio C3

6. 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 AU$271
includes taxes & fees
16 Oct - 17 Oct
Beach Front 1 Bedroom Flat D3

7. 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 AU$640
includes taxes & fees
28 Oct - 29 Oct
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

8. 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 AU$299
includes taxes & fees
28 Oct - 29 Oct
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

9. 1 BR 1 BA Simpson | Beach Access, Pool & Patio

1 BR 1 BA Simpson | Beach Access, Pool & Patio
Simpson Bay
The price is AU$260
includes taxes & fees
29 Oct - 30 Oct
1 BR 1 BA Simpson | Beach Access, Pool & Patio

10. 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 AU$320
includes taxes & fees
28 Oct - 29 Oct
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

11. C352 - Top view with balcony

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

12. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
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 AU$309
includes taxes & fees
28 Oct - 29 Oct
5 minutes walking from the beach 1-4B

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 AU$320
includes taxes & fees
16 Oct - 17 Oct
The Luxe 1 bedroom apartment with pool - GENERATOR (2-2A)

15. C301 – Beautiful Lagoon View Apartment

C301 – Beautiful Lagoon View Apartment
Cole Bay
The price is AU$494
includes taxes & fees
9 Nov - 10 Nov
C301 – Beautiful Lagoon View Apartment

16. Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
"Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating."
United States
Colleen M.
The price is AU$353
includes taxes & fees
2 Nov - 3 Nov
Maho Beach House: Studio Getaway, Oceanfront Vibe

17. A102 - Cozy Apartment with Garden

A102 - Cozy Apartment with Garden
Sint Maarten
A102 - Cozy Apartment with Garden

18. Utopia A3 | Beachside Stay @ The Drake Residences

Utopia A3 | Beachside Stay @ The Drake Residences
Simpson Bay
The price is AU$865
includes taxes & fees
18 Oct - 19 Oct
Utopia A3 | Beachside Stay @ The Drake Residences

19. D438 – Amazing 2-Bedroom Lagoon View with Balcony

D438 – Amazing 2-Bedroom Lagoon View with Balcony
Sint Maarten
8.0 out of 10, Very good, (1 review)
"Clean room, amazing view!! A little precarious getting up there though- should have more of a description of the challenge of getting to the unit!"
United States
ALLEN
D438 – Amazing 2-Bedroom Lagoon View with Balcony

20. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is AU$176
includes taxes & fees
16 Oct - 17 Oct
Blue Sail Apartments - Double room
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

Everything you need to know about Simpson Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Simpson Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay holiday rentals we have selected for you start as low as AU$115 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Simpson Bay has to offer?

Philips Scott House Calinago: This holiday 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 such as 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 holiday rentals are there in Simpson Bay?

With 38 Expedia holiday rentals, you're guaranteed 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 holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.