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, (1076)
"Perfect vacation "
The price is CA $311
CA $362 total
includes taxes & fees
Sep 7 - Sep 8
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 $223
CA $372 total
includes taxes & fees
Sep 11 - Sep 12
The Hills Residence

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 14 - Aug 15
Simpson Bay Suites

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

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.6 out of 10, Exceptional, (13)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

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

9.8 out of 10, Exceptional, (73)
"We chose the property based on proximity to family in the neighborhood and we could not have been happier with our selection. The private pool and access to beach was wonderful. The facility was beautiful and clean and suited our needs perfectly as the en suite bathroom for each bedroom was great."
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

Oceanfront amazing 2 bedrooms Condo

9.6 out of 10, Exceptional, (58)
"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!!

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

White Sands Retreat - Beachside at Beacon Hill

9.0 out of 10, Wonderful, (34)
"For us, this property was perfectly located & great for what we needed. Fast walk to a beach & wonderful beach restaurant, easy drives to other beaches & restaurants, beach equip, etc. property manager was so responsive & nice, as was the owner. We would stay there again. "
White Sands Retreat - Beachside at Beacon Hill

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 $447
CA $606 total
includes taxes & fees
Aug 14 - Aug 15
Turquoise paradise, directly ON beach, gated w underground parking!

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

9.6 out of 10, Exceptional, (48)
"Nice Villa. Prefect for families. Large living area. 3 nice bedrooms. Large kitchen with great appliances.Had no issues."
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea

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

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

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!

BEACHFRONT DESIGN VILLA

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

Nice and cozy ocean front studio with private terrace. Short walk to beaches.

9.4 out of 10, Exceptional, (18)
"Easy, no hassle accommodation. Short walk tl Maho beach, bars and shopping. Functional suite with a fabulous view"
Nice and cozy ocean front studio with private terrace. Short walk to beaches.

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
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?

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Simpson Bay are Ruby Room · CocoVaa Boutique Hotel - Ruby Suite and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 81 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.