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

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, (1,257 reviews)
"Rooms were clean and staff were great"
United States
Rosaida
$176 nightly
The price is $185
Aug 25 - Aug 26
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

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
$130 nightly
The price is $136
Jul 28 - Jul 29
Total with taxes and fees
Simpson Bay Suites

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
$254 nightly
The price is $266
Aug 3 - Aug 4
Total with taxes and fees
The Hills Residence

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.
$526 nightly
The price is $526
Jul 28 - Jul 29
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!

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, (6 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.
$422 nightly
The price is $422
Jul 28 - Jul 29
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

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
Jul 28 - Jul 29
Total with taxes and fees
Beach Front 1 Bedroom Flat D3

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
Jul 28 - Jul 29
Total with taxes and fees
Beach Front Studio C3

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
$123 nightly
The price is $123
Jul 28 - Jul 29
Total with taxes and fees
Blue Sail Apartments - Double room

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.
$210 nightly
The price is $216
Jul 28 - Jul 29
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Perfect location for us! We wanted easy access to see the planes coming in and it could not have been more perfect. Close to taxis and buses. Hosts were excellent at communicating. Friendly staff, would recommend!! "
United States
Laura
Maho Beach House Ocean Front Garden Studio

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
$217 nightly
The price is $223
Aug 3 - Aug 4
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
$340 nightly
The price is $356
Aug 2 - Aug 3
Total with taxes and fees
B225 - Incredible Lagoon View

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
$257 nightly
The price is $257
Jul 28 - Jul 29
Total with taxes and fees
Maho Beach Escape; Sunset Ocean View

Maho Beach Suite

Maho Beach Suite
Simpson Bay
$466 nightly
The price is $466
Aug 25 - Aug 26
Total with taxes and fees
Maho Beach Suite

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
$503 nightly
The price is $503
Jul 29 - Jul 30
Total with taxes and fees
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

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.
$879 nightly
The price is $879
Jul 28 - Jul 29
Total with taxes and fees
Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!

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
$143 nightly
The price is $143
Aug 4 - Aug 5
Total with taxes and fees
Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
$198 nightly
The price is $198
Jul 28 - Jul 29
Total with taxes and fees
Blue Sail Apartments - 1 bedroom apartments

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)
$932 nightly
The price is $932
Jul 28 - Jul 29
Total with taxes and fees
Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!

Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (172 reviews)
"Great stay! Beautiful suite"
United States
Crystal Alana
$326 nightly
The price is $339
Aug 6 - Aug 7
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
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
$277
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 $136 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 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.