Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (95 reviews)
"Clean rooms, amazing views, and responsive staff! Will be staying again next time. "
United States
Nicole
The price is CA $295
CA $362 total
includes taxes & fees
Mar 24 - Mar 25
The Hills Residence

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (144 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
The price is CA $231
CA $259 total
includes taxes & fees
Apr 6 - Apr 7
Simpson Bay Suites

Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
"Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating."
United States
Colleen M.
The price is CA $501
CA $647 total
includes taxes & fees
Mar 18 - Mar 19
Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.0 out of 10, Wonderful, (2 reviews)
"The location was very good. Located right by the Sunset Beach Bar and the arrival of the planes. The unit, itself, was great. Roomy for two. Nice patio area to watch the planes. The people that work in the building were very obliging and hospitable."
United States
Robin P.
Maho Beach House Ocean Front Garden Studio

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, (1,189 reviews)
"I don’t know why anyone would ever want to stay anywhere else! This place is the absolute best, nice beach, amazing staff, best location! "
Canada
Stefanie
The price is CA $525
CA $588 total
includes taxes & fees
Apr 3 - Apr 4
Hilton Vacation Club Royal Palm St. Maarten

Seafront Studio C4

Seafront Studio C4
Simpson Bay
10.0 out of 10, Exceptional, (3 reviews)
"My stay was amazing. Room was nice and cozy, located on strip near buccaneer beach. Everything was walking distance and the host was very kind and helpful and even gave me a gift. I traveled alone and felt extremely safe at this property. I will be returning!!"
United States
sacoya f.
Seafront Studio C4

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, (6 reviews)
"Very good place. Service very good. Keep up the good work lisa"
United States
Carlos
The price is CA $492
CA $676 total
includes taxes & fees
Mar 30 - Mar 31
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
"Great location near Simpson Bay restaurants and nightlife. Accommodations were exactly as pictured with modern furnishings. Car rental is recommended to fully enjoy the island. "
United States
Christopher
The price is CA $171
CA $256 total
includes taxes & fees
Mar 18 - Mar 19
Beach Front 1 Bedroom Flat D3

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.
The price is CA $244
CA $407 total
includes taxes & fees
Mar 31 - Apr 1
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

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

Modern apartment with shared pool and generator (2-2B)
Simpson Bay
The price is CA $275
CA $444 total
includes taxes & fees
Mar 19 - Mar 20
Modern apartment with shared pool and generator (2-2B)

5 minutes walking from the beach 1-4B

5 minutes walking from the beach 1-4B
Simpson Bay
The price is CA $269
CA $437 total
includes taxes & fees
Mar 18 - Mar 19
5 minutes walking from the beach 1-4B

A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View
Sint Maarten
The price is CA $362
CA $611 total
includes taxes & fees
Mar 24 - Mar 25
A116 - Immersive Simpson Bay Lagoon View

D403 - Very nice apartment with terrace

D403 - Very nice apartment with terrace
Cole Bay
10.0 out of 10, Exceptional, (1 review)
"Great spot for the money! The hill is tough as everyone says, but the staff do a great job taking you up and down as needed, or the cabs will drive you up if it’s after hours "
United Kingdom
Tony P.
The price is CA $315
CA $540 total
includes taxes & fees
Mar 23 - Mar 24
D403 - Very nice apartment with terrace

B256 - Amazing Top Floor Apartment With Balcony

B256 - Amazing Top Floor Apartment With Balcony
Sint Maarten
B256 - Amazing Top Floor Apartment With Balcony

A127 - Stunning 2-Bedroom Lagoon View

A127 - Stunning 2-Bedroom Lagoon View
Sint Maarten
6.0 out of 10, (1 review)
The price is CA $472
CA $762 total
includes taxes & fees
Mar 25 - Mar 26
A127 - Stunning 2-Bedroom Lagoon View

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is CA $226
CA $254 total
includes taxes & fees
Mar 24 - Mar 25
Blue Sail Apartments - 1 bedroom apartments

C321 - Spectacular Apartment with Lagoon Views

C321 - Spectacular Apartment with Lagoon Views
Sint Maarten
C321 - Spectacular Apartment with Lagoon Views

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (3 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
The price is CA $136
CA $218 total
includes taxes & fees
Apr 6 - Apr 7
Beach Front Studio C3

B236 - Homely Apartment with Balcony

B236 - Homely Apartment with Balcony
Sint Maarten
B236 - Homely Apartment with Balcony

Maho Beach Escape; Sunset Ocean View

Maho Beach Escape; Sunset Ocean View
Maho, Sint Maarten
10.0 out of 10, Exceptional, (4 reviews)
"Self check in and out was a nice experience "
United States
Kelva
The price is CA $501
CA $641 total
includes taxes & fees
Mar 20 - Mar 21
Maho Beach Escape; Sunset Ocean View
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
Next month
September
February
CA $372
Month
Price
January
CA $631
February
CA $651
March
CA $454
April
CA $372
May
CA $285
June
CA $246
July
CA $308
August
CA $280
September
CA $238
October
CA $276
November
CA $318
December
CA $434
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Simpson Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Philips Scott House Calinago: This vacation home rental outside Simpson Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Some other homes for rent in Simpson Bay include White Sands Retreat - Beachside at Beacon Hill and Dream Beachfront Home : Stunning sea views, private pool and walking distance .

How many vacation rentals are there in Simpson Bay?

With 40 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.