Simpson Bay Vacation Rentals

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Check prices for these dates

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Aug 7 - Aug 8
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Aug 8 - Aug 9
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Aug 8 - Aug 10
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Aug 15 - Aug 17

Vacation Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten
Relax by the pool surrounded by palm trees and lounge chairs.

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1070)
"The excellent service from ALL staff members on property. The property is so well maintained, well staffed and very friendly. "
The price is ￥32,613
￥38,101 total
includes taxes & fees
Aug 22 - Aug 23
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Relax on the balcony with a scenic view of the coastal town and distant mountains.

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
Enjoy breathtaking ocean views from this beachside retreat, where sailboats bob gently in the distance.

Simpson Bay Suites

3.5 star property
6.8 out of 10, (123)
"Highly recommended and friendly staff…"
The price is ￥15,870
￥17,774 total
includes taxes & fees
Aug 16 - Aug 17
Simpson Bay Suites
Tradewinds at Simpson Bay
Enjoy breathtaking marina views from our rooftop terrace, featuring lounge chairs and a pool.

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
Relax in comfort with a lounge chair and umbrella on the beach.

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
Enjoy a serene beach experience with gentle waves lapping at the shore.

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
Guests can enjoy breathtaking ocean views from their balcony or terrace.

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
Enjoy a serene beach view from this covered outdoor space with a white lattice design and blue railing.

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.
Enjoy meals in the kitchen with an oven and stainless steel sink, surrounded by a dining area with a round table and pendant light.

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!!
Relax by the pool overlooking the ocean, where you can enjoy a refreshing swim and access to the 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!
Enjoy breathtaking views of the turquoise sea from a balcony overlooking the sandy beach.

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 ￥47,756
￥64,654 total
includes taxes & fees
Aug 21 - Aug 22
Turquoise paradise, directly ON beach, gated w underground parking!
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
Enjoy stunning marina views from our hotel's modern design, featuring a flat roof and spacious balconies.

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
Enjoy the ocean view from this balcony with a wicker table and chairs.

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
Relax on the beach with two lounge chairs overlooking the calm sea and lush greenery.

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
Enjoy a tranquil beach experience with access to turquoise waters and a sailboat in the distance.

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
Relax by the ocean with a clear view from our poolside lounge chairs and seating area surrounded by palm trees.

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!
Relax on the deck with a clear view of the sea and distant boats.

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
Enjoy breathtaking views of the turquoise waters and serene beach surroundings.

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.
Enjoy breathtaking ocean views from this balcony with a clear view of the distant shoreline.

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
Relax by the pool surrounded by a deck and lounge chairs, with a serene view of the water and distant hills.

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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"The staff were very helpful and friendly."
Deanna 2-night trip
Posted 1 day ago
Simpson Bay Resort, Marina & Spa

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.