Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (158 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
$144 nightly
The price is $151
May 30 - May 31
Total with taxes and fees
Simpson Bay Suites

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, (1,234 reviews)
"This resort is absolutely amazing, our family enjoyed every minute. The pool and swim up bar are great and the private beach was fantastic. Its very centrally located close to airport and bars/restaurants,"
Canada
Curtis
$262 nightly
The price is $275
Jun 16 - Jun 17
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Maho Beach House - Spacious 1 Bedroom Suite

Maho Beach House - Spacious 1 Bedroom Suite
Maho, Sint Maarten
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Spacious room. "
Canada
Sinisa
$288 nightly
The price is $288
May 30 - May 31
Total with taxes and fees
Maho Beach House - Spacious 1 Bedroom Suite

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
Jun 7 - Jun 8
Total with taxes and fees
Blue Sail Apartments - Double room

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
Jun 1 - Jun 2
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
$357 nightly
The price is $376
Jun 2 - Jun 3
Total with taxes and fees
D416 – Relaxing apartment with Balcony

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
May 30 - May 31
Total with taxes and fees
Beach Front Studio C3

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.
$556 nightly
The price is $556
Jun 1 - Jun 2
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.
$462 nightly
The price is $462
Jun 2 - Jun 3
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
$189 nightly
The price is $189
May 30 - May 31
Total with taxes and fees
Beach Front 1 Bedroom Flat D3

Maho Beach Suite

Maho Beach Suite
Simpson Bay
$538 nightly
The price is $538
Jun 3 - Jun 4
Total with taxes and fees
Maho Beach Suite

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.
$223 nightly
The price is $229
May 31 - Jun 1
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

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.
$277 nightly
The price is $277
Jun 7 - Jun 8
Total with taxes and fees
Maho Beach House: Studio Getaway, Oceanfront Vibe

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.
$216 nightly
The price is $216
May 30 - May 31
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level

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
Jun 7 - Jun 8
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
$203 nightly
The price is $203
Jun 7 - Jun 8
Total with taxes and fees
Blue Sail Apartments - 1 bedroom apartments

Maho Beach House: Sunset Suite, 1-Bedroom

Maho Beach House: Sunset Suite, 1-Bedroom
Maho
10.0 out of 10, Exceptional, (1 review)
"We had a great stay. Noah and Dwayne were great to work with. They were quick to respond to any questions we had or help we needed. We enjoyed out daily walks and spent time enjoying 3 different beaches within walking distance as well great places to eat, drink and enjoy time in the sun."
United States
Dawn A.
$323 nightly
The price is $323
May 31 - Jun 1
Total with taxes and fees
Maho Beach House: Sunset Suite, 1-Bedroom

D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
$356 nightly
The price is $375
Jun 1 - Jun 2
Total with taxes and fees
D407 – Charming Apartment with Terrace
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
July
January
$279
Month
Price
January
$538
February
$538
March
$477
April
$369
May
$297
June
$279
July
$258
August
$273
September
$271
October
$265
November
$291
December
$462
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 $86 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.

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?

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Simpson Bay are Dream Beachfront Home : Stunning sea views, private pool and walking distance and New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many vacation rentals are there in Simpson Bay?

With 41 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.