Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.6 out of 10, Excellent, (65)
"Good location, walkable area, great views. "
United States
Tiffany
$296 nightly
The price is $310
Feb 2 - Feb 3
Total with taxes and fees
The Hills Residence

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
6.8 out of 10, (130)
"It is 'value priced', has a convenient location and the AC works :) But be realistic in your expectations, this is not competing with the Hiltons and Morgans on the island. Great for an overnight layover. Huge rooms - Really it's a full sized apartment with all the amenities. "
United States
Roger
$181 nightly
The price is $189
Jan 7 - Jan 8
Total with taxes and fees
Simpson Bay Suites
4.0 star property
9.0 out of 10, Wonderful, (1168)
"Room was great, resort was great, staff was great"
Canada
Gisele
$456 nightly
The price is $479
Jan 13 - Jan 14
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
10.0 out of 10, Exceptional, (2)
"perfect!!"
United States
jason l.
$308 nightly
The price is $318
Jan 13 - Jan 14
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
2.0 star property
$357 nightly
The price is $378
Jan 7 - Jan 8
Total with taxes and fees
D426 - Beautiful view of the lagoon with balcony

Apartment in Sint Maarten

C334 - Cozy Apartment with balcony
2.0 star property
$357 nightly
The price is $378
Jan 7 - Jan 8
Total with taxes and fees
C334 - Cozy Apartment with balcony
2.0 star property
$346 nightly
The price is $367
Jan 9 - Jan 10
Total with taxes and fees
C302 – Modern Comfort with Private Terrace
10.0 out of 10, Exceptional, (2)
"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.
$402 nightly
The price is $402
Feb 2 - Feb 3
Total with taxes and fees
Maho Beach House: Studio Getaway, Oceanfront Vibe
2.0 star property
$435 nightly
The price is $435
Jan 8 - Jan 9
Total with taxes and fees
D428 – Spacious 2-Bedroom Lagoon View with Balcony
10.0 out of 10, Exceptional, (1)
"We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful."
United States
Trish S.
$442 nightly
The price is $461
Jan 6 - Jan 7
Total with taxes and fees
Marina Views in the Heart of Simpson Bay
2.0 star property
$348 nightly
The price is $369
Jan 19 - Jan 20
Total with taxes and fees
C321 - Spectacular Apartment with Lagoon Views
2.0 star property
$537 nightly
The price is $561
Jan 6 - Jan 7
Total with taxes and fees
Modern 2BR Villa | Beach Access | Mins to Maho
9.4 out of 10, Exceptional, (3)
"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.
$344 nightly
The price is $344
Jan 29 - Jan 30
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level
$336 nightly
The price is $356
Jan 9 - Jan 10
Total with taxes and fees
B242 - Glorious Lagoon View Apartment with Balcony

Apartment in Sint Maarten

C337 - Charming 2-Bedroom Lagoon View
2.0 star property
$438 nightly
The price is $465
Jan 11 - Jan 12
Total with taxes and fees
C337 - Charming 2-Bedroom Lagoon View
8.6 out of 10, Excellent, (4)
"Welcoming love the area we will be coming back thank you so much "
United States
Juan D.
Maho Beach Garden Studio with Beach Access
2.0 star property
$642 nightly
The price is $671
Jan 7 - Jan 8
Total with taxes and fees
Modern 2BR Townhome | Walk to Maho & SXM Planes
$351 nightly
The price is $372
Jan 7 - Jan 8
Total with taxes and fees
A105 - Breathtaking Apartment with Garden
10.0 out of 10, Exceptional, (2)
"This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again"
United States
JEROME J.
$943 nightly
The price is $984
Feb 5 - Feb 6
Total with taxes and fees
Sunny Days at Simpson Bay Yacht Club
2.0 star property
$796 nightly
The price is $832
Jan 26 - Jan 27
Total with taxes and fees
Maho Beach 3BR Villa | Huge Terrace & Runway 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
This month
Next month
October
January
$418
$416
Month
Price
January
$418
February
$416
March
$416
April
$373
May
$288
June
$289
July
$303
August
$280
September
$260
October
$248
November
$277
December
$400
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 $189 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 lively bars and top-notch restaurants.

What are some of the best vacation home rentals that Simpson Bay has to offer?

Maho Beach House Ocean Front Garden Studio: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Charming 3BR Villa w Private Pool in Pelican Key.

How many vacation rentals are there in Simpson Bay?

With 40 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.