Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

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, (1,216 reviews)
"Great hotel and family friendly."
United States
Joseph
The price is CA $391
CA $447 total
includes taxes & fees
May 31 - Jun 1
Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (155 reviews)
"AC worked well the room was cleaned daily and the staff was always friendly and made great suggestions for dinning and places to see."
United States
Michael
The price is CA $183
CA $205 total
includes taxes & fees
May 4 - May 5
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 $261
CA $373 total
includes taxes & fees
May 16 - May 17
Maho Beach House: Studio Getaway, Oceanfront Vibe

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (128 reviews)
"Great location "
United States
Orandy
The Hills Residence

D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
The price is CA $280
CA $509 total
includes taxes & fees
May 3 - May 4
D416 – Relaxing apartment with Balcony

Maho Beach House: Sunset Suite, 1-Bedroom

Maho Beach House: Sunset Suite, 1-Bedroom
Maho
10.0 out of 10, Exceptional, (1 review)
"We had a great stay. Noah and Dwayne were great to work with. They were quick to respond to any questions we had or help we needed. We enjoyed out daily walks and spent time enjoying 3 different beaches within walking distance as well great places to eat, drink and enjoy time in the sun."
United States
Dawn A.
Maho Beach House: Sunset Suite, 1-Bedroom

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)
"Great place to stay with a lot of privacy and walkable to stores and restaurants. Amazing views! Lisa is so friendly and keeps the place amazing!"
United States
Alaciel S.
The price is CA $439
CA $611 total
includes taxes & fees
May 20 - May 21
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is CA $172
CA $201 total
includes taxes & fees
May 6 - May 7
Blue Sail Apartments - Two bedroom apartments

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

Turquoise paradise, directly ON beach, gated w underground parking!
Simpson Bay
9.8 out of 10, Exceptional, (22 reviews)
"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! "
United States
Rachel S.
The price is CA $581
CA $755 total
includes taxes & fees
Jun 1 - Jun 2
Turquoise paradise, directly ON beach, gated w underground parking!

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (3 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 $170
CA $254 total
includes taxes & fees
May 6 - May 7
Beach Front 1 Bedroom Flat D3

front-balcony beach view and the back-balcony main airport View

front-balcony beach view and the back-balcony main airport View
Simpson Bay
The price is CA $292
CA $372 total
includes taxes & fees
May 5 - May 6
front-balcony beach view and the back-balcony main airport View

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 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 $134
CA $216 total
includes taxes & fees
May 3 - May 4
Beach Front Studio C3

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 $156
CA $300 total
includes taxes & fees
May 3 - May 4
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Incredible property. Views for days, great location. Had a wonderful stay and Lisa was great also. Very secure condo and clean. Loved the pool and so many dining options close by. "
United States
Camelo
The price is CA $488
CA $671 total
includes taxes & fees
May 3 - May 4
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

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 $244
CA $348 total
includes taxes & fees
May 4 - May 5
Maho Beach Escape; Sunset Ocean View

Maho Beach House: Sand Bar Suite, 2-Bedroom

Maho Beach House: Sand Bar Suite, 2-Bedroom
Maho, Sint Maarten
The price is CA $434
CA $610 total
includes taxes & fees
May 26 - May 27
Maho Beach House: Sand Bar Suite, 2-Bedroom

Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is CA $509
CA $696 total
includes taxes & fees
May 26 - May 27
Maho Beach Suite

D406 - Incredible Apartment With Terrace

D406 - Incredible Apartment With Terrace
Cole Bay
The price is CA $280
CA $499 total
includes taxes & fees
May 6 - May 7
D406 - Incredible Apartment With Terrace

D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
The price is CA $280
CA $509 total
includes taxes & fees
May 6 - May 7
D407 – Charming Apartment with Terrace

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is CA $244
CA $277 total
includes taxes & fees
May 2 - May 3
Blue Sail Apartments - 1 bedroom apartments
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
This month
Next month
September
January
CA $262
CA $246
Month
Price
January
CA $478
February
CA $474
March
CA $445
April
CA $319
May
CA $262
June
CA $246
July
CA $307
August
CA $279
September
CA $220
October
CA $246
November
CA $325
December
CA $455
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 New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

How many vacation rentals are there in Simpson Bay?

With 41 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.