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
7.0 out of 10, Good, (133 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
$181 nightly
The price is $189
Mar 17 - Mar 18
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, (1,179 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
$475 nightly
The price is $499
Feb 20 - Feb 21
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very Good, (82 reviews)
"Great staff, would stay again!"
United States
Maimuna
$357 nightly
The price is $373
Feb 26 - Feb 27
Total with taxes and fees
The Hills Residence

Charming 3BR Villa w Private Pool in Pelican Key

Charming 3BR Villa w Private Pool in Pelican Key
Pelican Key
$945 nightly
The price is $1,028
Mar 3 - Mar 4
Total with taxes and fees
Charming 3BR Villa w Private Pool in Pelican Key

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
$528 nightly
The price is $528
Feb 28 - Mar 1
Total with taxes and fees
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
9.4 out of 10, Exceptional, (3 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.
$357 nightly
The price is $357
Mar 9 - Mar 10
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level

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.
$540 nightly
The price is $540
Feb 19 - Feb 20
Total with taxes and fees
Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
8.0 out of 10, Very Good, (1 review)
$276 nightly
The price is $276
Mar 17 - Mar 18
Total with taxes and fees
Maho Beach House Ocean Front Garden Studio

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Beacon Hill Hideaway: Luxury Condo in Simpson Bay
Simpson Bay
$692 nightly
The price is $722
Mar 3 - Mar 4
Total with taxes and fees
Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
$205 nightly
The price is $205
Mar 8 - Mar 9
Total with taxes and fees
Beach Front 1 Bedroom Flat D3

Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
10.0 out of 10, Exceptional, (1 review)
"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
$233 nightly
The price is $233
Feb 27 - Feb 28
Total with taxes and fees
Blue Sail Apartments - Two bedroom apartments

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (3 reviews)
"Clean and modern. Need a door for the bathroom. Check in was easy and Lisa was there to help us get checked in. She even provided 2 cold water and 2 cold beers"
United States
Norman
$159 nightly
The price is $159
Feb 23 - Feb 24
Total with taxes and fees
Beach Front Studio C3

D408 – Chic & Stylish 2 Bedroom with Terrace

D408 – Chic & Stylish 2 Bedroom with Terrace
Sint Maarten
$519 nightly
The price is $552
Feb 16 - Feb 17
Total with taxes and fees
D408 – Chic & Stylish 2 Bedroom with Terrace

C337 - Charming 2-Bedroom Lagoon View

C337 - Charming 2-Bedroom Lagoon View
Sint Maarten
$499 nightly
The price is $531
Feb 18 - Feb 19
Total with taxes and fees
C337 - Charming 2-Bedroom Lagoon View

A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
$399 nightly
The price is $424
Mar 7 - Mar 8
Total with taxes and fees
A101 - Outstanding Lagoon View & Garden

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
$312 nightly
The price is $322
Feb 18 - Feb 19
Total with taxes and fees
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

B256 - Amazing Top Floor Apartment With Balcony

B256 - Amazing Top Floor Apartment With Balcony
Sint Maarten
$383 nightly
The price is $406
Feb 26 - Feb 27
Total with taxes and fees
B256 - Amazing Top Floor Apartment With Balcony

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
8.6 out of 10, Excellent, (4 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.
$463 nightly
The price is $463
Feb 17 - Feb 18
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.0 out of 10, Wonderful, (2 reviews)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
$392 nightly
The price is $392
Feb 23 - Feb 24
Total with taxes and fees
Maho Beach House - Petit Studio Océanique - Charmante Vue

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
$508 nightly
The price is $508
Feb 21 - Feb 22
Total with taxes and fees
Maho Beach Escape; Sunset Ocean 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
September
January
$460
$380
Month
Price
January
$506
February
$460
March
$380
April
$366
May
$294
June
$283
July
$282
August
$283
September
$272
October
$281
November
$307
December
$495
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.

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?

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 White Sands Retreat - Beachside at Beacon Hill and New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many vacation rentals are there in Simpson Bay?

With 34 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.