Simpson Bay Vacation Rentals

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Our top choices for Simpson Bay vacation rentals

D416 – Relaxing apartment with Balcony

D416 – Relaxing apartment with Balcony
Sint Maarten
$357 nightly
The price is $376
May 11 - May 12
Total with taxes and fees
D416 – Relaxing apartment with Balcony

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.
$560 nightly
The price is $560
Jun 1 - Jun 2
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!

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
$495 nightly
The price is $495
May 10 - May 11
Total with taxes and fees
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Maho Beach House: Sand Bar Suite, 2-Bedroom

Maho Beach House: Sand Bar Suite, 2-Bedroom
Maho, Sint Maarten
$450 nightly
The price is $450
May 25 - May 26
Total with taxes and fees
Maho Beach House: Sand Bar Suite, 2-Bedroom

Maho Beach Suite

Maho Beach Suite
Simpson Bay
$475 nightly
The price is $475
May 26 - May 27
Total with taxes and fees
Maho Beach Suite

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (157 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
$144 nightly
The price is $151
May 10 - May 11
Total with taxes and fees
Simpson Bay Suites

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
$206 nightly
The price is $206
May 10 - May 11
Total with taxes and fees
Blue Sail Apartments - 1 bedroom apartments

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, (1,223 reviews)
"This resort is absolutely amazing, our family enjoyed every minute. The pool and swim up bar are great and the private beach was fantastic. Its very centrally located close to airport and bars/restaurants,"
Canada
Curtis
$237 nightly
The price is $248
May 17 - May 18
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten

Garden view Simpson Bay apartment with pool-GENERATOR (2-1B)

Garden view Simpson Bay apartment with pool-GENERATOR (2-1B)
Simpson Bay
$279 nightly
The price is $286
May 11 - May 12
Total with taxes and fees
Garden view Simpson Bay apartment with pool-GENERATOR (2-1B)

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Perfect location for us! We wanted easy access to see the planes coming in and it could not have been more perfect. Close to taxis and buses. Hosts were excellent at communicating. Friendly staff, would recommend!! "
United States
Laura
$230 nightly
The price is $230
May 10 - May 11
Total with taxes and fees
Maho Beach House Ocean Front Garden Studio

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
$159 nightly
The price is $159
May 10 - May 11
Total with taxes and fees
Beach Front Studio C3

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
$189 nightly
The price is $189
May 10 - May 11
Total with taxes and fees
Beach Front 1 Bedroom Flat D3

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.
$455 nightly
The price is $455
May 18 - May 19
Total with taxes and fees
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

D406 - Incredible Apartment With Terrace

D406 - Incredible Apartment With Terrace
Cole Bay
$348 nightly
The price is $367
May 13 - May 14
Total with taxes and fees
D406 - Incredible Apartment With Terrace

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.
$306 nightly
The price is $306
May 14 - May 15
Total with taxes and fees
Maho Beach House: Sunset Suite, 1-Bedroom

D434 - Amazing Apartment with Balcony

D434 - Amazing Apartment with Balcony
Sint Maarten
$358 nightly
The price is $377
May 10 - May 11
Total with taxes and fees
D434 - Amazing Apartment with Balcony

D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace
Sint Maarten
$357 nightly
The price is $376
May 11 - May 12
Total with taxes and fees
D407 – Charming Apartment with Terrace

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.
$217 nightly
The price is $223
May 11 - May 12
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
9.6 out of 10, Exceptional, (4 reviews)
"The Maho was very clean, quiet and close to the airport. I recommend for people passing through or for a few days on St. Martins."
United States
David V.
$215 nightly
The price is $215
May 13 - May 14
Total with taxes and fees
Maho Beach Modern 1-Bedroom, Ocean Level

Lux Maho Reef 1BR Suite - Brand New - Best Location!

Lux Maho Reef 1BR Suite - Brand New - Best Location!
Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
$317 nightly
The price is $317
May 10 - May 11
Total with taxes and fees
Lux Maho Reef 1BR Suite - Brand New - Best Location!
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
May
January
$245
$284
Month
Price
January
$510
February
$417
March
$410
April
$341
May
$245
June
$284
July
$273
August
$245
September
$251
October
$266
November
$320
December
$510
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

Everything you need to know about Simpson Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpson Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Simpson Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 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.