Simpson Bay Vacation Rentals from $159: Search Short-Term Rentals

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

Charming 3BR Villa w Private Pool in Pelican Key : Visitors like this Simpson Bay vacation home rental. It offers a balcony, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 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 White Sands Retreat - Beachside at Beacon Hill and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

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Our top choices for Simpson Bay vacation rentals

Beach nearby, white sand, sun loungers, beach umbrellas

Aparthotel in Simpson Bay

Roger

$181 nightly

Jan 11 - Jan 12

Total with taxes and fees

Aparthotel in Simpson Bay

Tiffany

$307 nightly

Feb 2 - Feb 3

Total with taxes and fees

On the beach, sun loungers, beach umbrellas, beach towels

Aparthotel in Simpson Bay

Gisele

$408 nightly

Jan 15 - Jan 16

Total with taxes and fees

Apartment in Simpson Bay

jason l.

$312 nightly

Jan 13 - Jan 14

Total with taxes and fees

Vacation Home in Simpson Bay

$663 nightly

Jan 19 - Jan 20

Total with taxes and fees

Apartment in Simpson Bay

Trish S.

$429 nightly

Jan 11 - Jan 12

Total with taxes and fees

Condo in Maho, Sint Maarten

Colleen M.

$381 nightly

Jan 11 - Jan 12

Total with taxes and fees

Apartment in Sint Maarten

$341 nightly

Feb 2 - Feb 3

Total with taxes and fees

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Top Simpson Bay Hotel Reviews

Baker's Suites

10/10 Excellent

"Great staff and location"

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent

"We were at this hotel for 10 days (end of November 2025). The room was very clean. The room location was great as we faced the beach. We were on the second level which made it very convenient/walkable between the beach and the room. The kitchen in the room included everything that you need including paper towels, dishwasher soap, cleaning sponges , salt, pepper, dishes, pots and pans..etc. Hotel location was great (walking distance to many restaurants). Ample parking spaces (not sure why others said it was limited, they may have not known the parking under the hotel). Staff were amazing (both at the front desk and cleaning staff-not sure why some visitors had issues with the front desk as they were very courteous and professional-Tessy was the best). Our room was cleaned every 3 days (witout having to request the cleaning unlike some of the other reviews hear). The hotel staff communicated via text message so it would be helpful to have a phone plan to use at the island. The beaches at the hotel was just awesome. Waters were always calm. There is sand in the water so no need for rock shoes. Great snorkeling within the bay at the hotel as well as further out where you can find sea turtles and sting rays. This hotel, location and staff make it a 10/10 place to visit. We will be visiting again!"

Commodore Suites

10/10 Excellent

"We stayed eleven days here and the room that we had was the studio suit. Spacious for a long stay and the best air conditioner I ever had on an Island. The market on the main floor had everything we needed. The only issue we had was we planned a cookout on the rooftop for New Year's Eve. The Commodore has two gas grills for guest. We cleaned and seasoned are meat that afternoon but when we started to grill that evening the gas tanks were empty. We immediately reported this to the front desk thinking that they must have other tanks since we had set this up six days prior. The manager was notified by phone, but nothing they could do because it's getting late. Finally, the front desk clerk Lereisha came into action. She had her father come get the tank to get it filled at 9PM and he saved the celebration night. It was six of us planning to eat from the cookout. Lereisha showed how what customer service should be and stepped up to the plate, Thank you so much. Shout out to the other clerks Arella, and Shanilla who was always willing to help us. We will be back."

Hilton Vacation Club Royal Palm St. Maarten

10/10 Excellent

"The location is super convenient for everything, whether walking to restaurants or getting to other parts of the island. Room was spotless and well laid out and the views of the Caribbean sunset from the balcony couldn’t be better. Staff was amazing and on site restaurant was very good as well. We rented a car and parking was included and secure. I would stay here again but be warned it can be loud late into the night from the bar across the street. Especially Sunday night ironically. "

Price trends for vacation rentals in Simpson Bay

Less expensive	More expensive	This month	Next month
October	February	$404	$413

Month	Price
January	$404
February	$413
March	$391
April	$368
May	$305
June	$284
July	$304
August	$283
September	$263
October	$257
November	$280
December	$361

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 $159 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.

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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?

Charming 3BR Villa w Private Pool in Pelican Key: Visitors like this Simpson Bay vacation home rental. It offers a balcony, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 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 White Sands Retreat - Beachside at Beacon Hill and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 37 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.

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Check prices for these dates

Our top choices for Simpson Bay vacation rentals

Aparthotel in Simpson Bay

Aparthotel in Simpson Bay

Aparthotel in Simpson Bay

Apartment in Simpson Bay

Vacation Home in Simpson Bay

Apartment in Simpson Bay

Condo in Maho, Sint Maarten

Apartment in Sint Maarten

Condo in Maho

Apartment in Sint Maarten

Apartment in Sint Maarten

Apartment in Sint Maarten

Condo in Simpson Bay

Vacation Home in Simpson Bay

Apartment in Simpson Bay

Vacation Home in Simpson Bay

Condo in Simpson Bay

Condo in Simpson Bay

Vacation Home in Pelican Key

Apartment in Simpson Bay

Find vacation rentals that suit your style

Top Simpson Bay Hotel Reviews

Baker's Suites

Price trends for vacation rentals in Simpson Bay

Find out more about Simpson Bay

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