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, (132 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
$192 nightly
The price is $200
Feb 7 - Feb 8
Total with taxes and fees
Simpson Bay Suites

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.6 out of 10, Excellent, (78 reviews)
"Great staff, would stay again!"
United States
Maimuna
$331 nightly
The price is $347
Feb 20 - Feb 21
Total with taxes and fees
The Hills Residence

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
10.0 out of 10, Exceptional, (2 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 22 - Feb 23
Total with taxes and fees
Beach Front Studio C3

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, (1,177 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
$408 nightly
The price is $428
Mar 1 - Mar 2
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
$115 nightly
The price is $115
Feb 8 - Feb 9
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.
$312 nightly
The price is $322
Feb 12 - Feb 13
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

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.
$335 nightly
The price is $335
Feb 23 - Feb 24
Total with taxes and fees
Maho Beach House - Petit Studio Océanique - Charmante Vue

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Simpson Bay
9.6 out of 10, Exceptional, (17 reviews)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
$451 nightly
The price is $466
Feb 10 - Feb 11
Total with taxes and fees
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

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)

Modern apartment with shared pool and generator (2-2B)

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
$316 nightly
The price is $326
Feb 8 - Feb 9
Total with taxes and fees
Modern apartment with shared pool and generator (2-2B)

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.
$445 nightly
The price is $445
Feb 13 - Feb 14
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level

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, (3 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.
$487 nightly
The price is $487
Mar 2 - Mar 3
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

B245 - Condo with amazing view

B245 - Condo with amazing view
Sint Maarten
$364 nightly
The price is $385
Feb 20 - Feb 21
Total with taxes and fees
B245 - Condo with amazing view

C344 - Lagoon view with balcony

C344 - Lagoon view with balcony
Simpson Bay
$399 nightly
The price is $424
Feb 9 - Feb 10
Total with taxes and fees
C344 - Lagoon view with balcony

A134 - Panoramic View of the Lagoon

A134 - Panoramic View of the Lagoon
Sint Maarten
$389 nightly
The price is $413
Feb 9 - Feb 10
Total with taxes and fees
A134 - Panoramic View of the Lagoon

A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
$387 nightly
The price is $410
Feb 10 - Feb 11
Total with taxes and fees
A116 - Immersive Simpson Bay Lagoon View

C337 - Charming 2-Bedroom Lagoon View

C337 - Charming 2-Bedroom Lagoon View
Sint Maarten
$493 nightly
The price is $525
Feb 18 - Feb 19
Total with taxes and fees
C337 - Charming 2-Bedroom Lagoon View

B256 - Amazing Top Floor Apartment With Balcony

B256 - Amazing Top Floor Apartment With Balcony
Sint Maarten
$384 nightly
The price is $407
Feb 26 - Feb 27
Total with taxes and fees
B256 - Amazing Top Floor Apartment With Balcony

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)
$340 nightly
The price is $340
Feb 15 - Feb 16
Total with taxes and fees
Maho Beach House Ocean Front Garden Studio

A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
$399 nightly
The price is $424
Feb 12 - Feb 13
Total with taxes and fees
A101 - Outstanding Lagoon View & Garden
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
$398
$343
Month
Price
January
$512
February
$398
March
$343
April
$360
May
$278
June
$282
July
$282
August
$279
September
$275
October
$279
November
$304
December
$499
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 $200 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?

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 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.