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Top Holiday 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 £153
includes taxes & fees
2 Sept - 3 Sept
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 Hills Residence

Simpson Bay Suites

3.5 star property
6.8 out of 10, (123)
"Highly recommended and friendly staff…"
The price is £91
includes taxes & fees
5 Aug - 6 Aug
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

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 £338
includes taxes & fees
5 Aug - 6 Aug
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)
"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

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

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

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

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!

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

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 holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Simpson Bay has to offer?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : This highly rated holiday home rental in Simpson Bay is located on the beach, and has an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. Other favourite 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 holiday rentals are there in Simpson Bay?

With 80 Expedia holiday rentals, you're guaranteed 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 holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.