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, (1,270 reviews)
"It was a great stay"
United States
Shawn
The price is NZ$286
includes taxes & fees
25 Aug - 26 Aug
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, (164 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is NZ$460
includes taxes & fees
16 Sept - 17 Sept
The Hills Residence

3. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (163 reviews)
"It was good value for money."
United States
Tirichmir
The price is NZ$229
includes taxes & fees
27 Aug - 28 Aug
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 NZ$268
includes taxes & fees
21 Aug - 22 Aug
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 NZ$314
includes taxes & fees
21 Aug - 22 Aug
Beach Front 1 Bedroom Flat D3

6. 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 NZ$353
includes taxes & fees
18 Sept - 19 Sept
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

7. 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 NZ$248
includes taxes & fees
31 Aug - 1 Sept
Blue Sail Apartments - Two bedroom apartments

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 NZ$364
includes taxes & fees
18 Sept - 19 Sept
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

9. 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 NZ$748
includes taxes & fees
18 Sept - 19 Sept
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

10. C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
C344 - Lagoon view with balcony

11. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is NZ$594
includes taxes & fees
18 Sept - 19 Sept
D416 – Relaxing apartment with Balcony

12. C352 - Top view with balcony

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

13. 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 NZ$876
includes taxes & fees
21 Aug - 22 Aug
Turquoise paradise, directly ON beach, gated w underground parking!

14. C302 – Modern Comfort with Private Terrace

C302 – Modern Comfort with Private Terrace
Simpson Bay
The price is NZ$588
includes taxes & fees
2 Sept - 3 Sept
C302 – Modern Comfort with Private Terrace

15. 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 NZ$422
includes taxes & fees
21 Aug - 22 Aug
Maho Beach Escape; Sunset Ocean View

16. C314 - Stunning 1 Bedroom Apartment

C314 - Stunning 1 Bedroom Apartment
Sint Maarten
C314 - Stunning 1 Bedroom Apartment

17. A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
A101 - Outstanding Lagoon View & Garden

18. C347 – Stylish 2 Bedroom

C347 – Stylish 2 Bedroom
Sint Maarten
The price is NZ$848
includes taxes & fees
23 Aug - 24 Aug
C347 – Stylish 2 Bedroom

19. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is NZ$213
includes taxes & fees
21 Aug - 22 Aug
Blue Sail Apartments - Double room

20. 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
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 favorite 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 depends 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 NZ$152 per night. Entering your travel dates in the search wizard you might find 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?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : This highly rated holiday home rental in Simpson Bay is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Simpson Bay are New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and White Sands Retreat - Beachside at Beacon Hill.

How many holiday rentals are there in Simpson Bay?

With 45 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. Simpson Bay Beach and Hollywood Casino 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.