Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1066)
"Perfect location for dining, partying and shoping"
The price is CA $233
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
9.0 out of 10, Wonderful, (37)
"Love the view first of all. Property was in a great location. "
The price is CA $214
CA $363 total
includes taxes & fees
Sep 1 - Sep 2
The Hills Residence

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (28)
"We enjoyed the stay to the fullest"
Tradewinds at Simpson Bay

Simpson Bay Suites

3.5 star property
6.8 out of 10, (123)
"Highly recommended and friendly staff…"
The price is CA $149
CA $167 total
includes taxes & fees
Aug 5 - Aug 6
Simpson Bay Suites

One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

9.8 out of 10, Exceptional, (72)
"We loved this house with the sound of the waves and the ocean front view. Pool was great and was a wonderful place to hang out. The house is Close to many things but still feels very private. House was clean and had everything we needed to cook most our meals. "
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.8 out of 10, Exceptional, (12)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Oceanfront amazing 2 bedrooms Condo

9.8 out of 10, Exceptional, (57)
"Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!"
Oceanfront amazing 2 bedrooms Condo

The Horny Toad Guesthouse

3.0 star property
9.4 out of 10, Exceptional, (53)
"We like it being beachfront, wide verandas, spacious unit, host and staff were excellent!"
The Horny Toad Guesthouse

A curated two bedroom suite near Maho beach.

10.0 out of 10, Exceptional, (2)
"Great place. Nice and quite with beaches close "
A curated two bedroom suite near Maho beach.

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

10.0 out of 10, Exceptional, (102)
"Super great time. Best location for all activities. Would stay again."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

Turquoise paradise, directly ON beach, gated w underground parking!

9.8 out of 10, Exceptional, (20)
"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! "
The price is CA $448
CA $605 total
includes taxes & fees
Aug 5 - Aug 6
Turquoise paradise, directly ON beach, gated w underground parking!

Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

10.0 out of 10, Exceptional, (9)
"Will stay again. "
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

1-bedroom condo in amazing Simpson Bay Pool Steps from the beach, with WiFi, AC

1-bedroom condo in amazing Simpson Bay Pool Steps from the beach, with WiFi, AC

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (119)
"Great stay, house well equipped, would book it again. "
BEACHFRONT DESIGN VILLA

Top of the art penthouse on the beach - 4000 sq. ft of luxury

10.0 out of 10, Exceptional, (75)
"Amazing property Fantastic location Incredible views Great getaway "
Top of the art penthouse on the beach - 4000 sq. ft of luxury

Luxury Penthouse with Private Rooftop Directly on Beach, Best Location, pool!

10.0 out of 10, Exceptional, (2)
"The entire complex was nice and well kept. Very close to the airport with stellar views! The unit was very clean and was overall a great experience. I would stay there again. "
Luxury Penthouse with Private Rooftop Directly on Beach, Best Location, pool!

Oceanfront amazing 2 BR Villa - 2 min from the beach

9.4 out of 10, Exceptional, (95)
"Good stay nice place property is comfortable, quiet, private, easily accessible, amenities worked well, kitchen very well equipment. Enjoyed my stay so did my group."
Oceanfront amazing 2 BR Villa - 2 min from the beach

Anchor House - Direct Oceanfront - Luxury & Modern Style

10.0 out of 10, Exceptional, (145)
"The property itself was beautiful and the view was or if this world! Access to nightlife, beaches, restaurants was perfect. So quiet and peaceful. We were so sad to leave!"
Anchor House - Direct Oceanfront - Luxury & Modern Style

Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

9.6 out of 10, Exceptional, (48)
"Had a great time with friends great house very nice pool nice sun set views"
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

Cliff House

3.5 star property
8.8 out of 10, Excellent, (3)
"Great stay at the Cliff house. Very private accommodations and plenty of room for a couple or a family experience. Easy parking, but only a short 7 minute walk into town. "
Cliff House
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

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 Charming 3BR Villa w Private Pool in Pelican Key and Ruby Room · CocoVaa Boutique Hotel - Ruby Suite.

How many vacation rentals are there in Simpson Bay?

With 80 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?

Flamingo Beach and Simpson Bay Beach are a couple of lovely local spots to get outside and enjoy nature. Kim Sha 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.