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, (1,270 reviews)
"It was a great stay"
United States
Shawn
$176 nightly
The price is $185
Aug 27 - Aug 28
Total with taxes and fees
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, (163 reviews)
"It was good value for money."
United States
Tirichmir
$130 nightly
The price is $136
Aug 22 - Aug 23
Total with taxes and fees
Simpson Bay Suites

3. 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
$244 nightly
The price is $256
Sep 3 - Sep 4
Total with taxes and fees
The Hills Residence

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
$159 nightly
The price is $159
Aug 23 - Aug 24
Total with taxes and fees
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
$188 nightly
The price is $188
Aug 22 - Aug 23
Total with taxes and fees
Beach Front 1 Bedroom Flat D3

6. 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
$147 nightly
The price is $147
Aug 25 - Aug 26
Total with taxes and fees
Blue Sail Apartments - Two bedroom apartments

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.
$211 nightly
The price is $217
Aug 26 - Aug 27
Total with taxes and fees
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
8.8 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.
$421 nightly
The price is $421
Aug 22 - Aug 23
Total with taxes and fees
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
$216 nightly
The price is $222
Aug 23 - Aug 24
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

10. D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
$339 nightly
The price is $355
Sep 5 - Sep 6
Total with taxes and fees
D416 – Relaxing apartment with Balcony

11. Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
9.6 out of 10, Exceptional, (4 reviews)
"The Maho was very clean, quiet and close to the airport. I recommend for people passing through or for a few days on St. Martins."
United States
David V.
$203 nightly
The price is $203
Aug 22 - Aug 23
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level

12. 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.
$525 nightly
The price is $525
Aug 22 - Aug 23
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!

13. 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
$243 nightly
The price is $243
Aug 24 - Aug 25
Total with taxes and fees
Maho Beach Escape; Sunset Ocean View

14. D402 - Beautiful apartment with garden and view

D402 - Beautiful apartment with garden and view
Cole Bay
$353 nightly
The price is $370
Aug 25 - Aug 26
Total with taxes and fees
D402 - Beautiful apartment with garden and view

15. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
$126 nightly
The price is $126
Aug 25 - Aug 26
Total with taxes and fees
Blue Sail Apartments - Double room

16. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
$204 nightly
The price is $204
Aug 25 - Aug 26
Total with taxes and fees
Blue Sail Apartments - 1 bedroom apartments

17. C322 - Beautiful 1-Bedroom Unit with Balcony

C322 - Beautiful 1-Bedroom Unit with Balcony
Sint Maarten
$340 nightly
The price is $356
Sep 16 - Sep 17
Total with taxes and fees
C322 - Beautiful 1-Bedroom Unit with Balcony

18. B256 - Amazing Top Floor Apartment With Balcony

B256 - Amazing Top Floor Apartment With Balcony
Sint Maarten
$339 nightly
The price is $355
Sep 6 - Sep 7
Total with taxes and fees
B256 - Amazing Top Floor Apartment With Balcony

19. 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
$506 nightly
The price is $506
Aug 22 - Aug 23
Total with taxes and fees
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

20. B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
$338 nightly
The price is $354
Aug 23 - Aug 24
Total with taxes and fees
B225 - Incredible Lagoon View
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

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
Next month
October
February
$281
Month
Price
January
$523
February
$539
March
$419
April
$392
May
$304
June
$268
July
$256
August
$277
September
$281
October
$243
November
$293
December
$482
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Simpson Bay. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Simpson Bay

Everything you need to know about Simpson Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpson Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Simpson Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. Other favorite 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 vacation rentals are there in Simpson Bay?

With 45 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. Simpson Bay Beach and Hollywood Casino 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.