Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Simpson Bay vacation rentals

Amazing Top Floor Apartment | Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.6 out of 10, Excellent, (88 reviews)
"Great staff, would stay again!"
United States
Maimuna
The Hills Residence
Beach nearby, white sand, sun loungers, beach umbrellas

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (137 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
The price is ￥26,134
￥29,270 total
includes taxes & fees
Mar 21 - Mar 22
Simpson Bay Suites
Exterior

Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
9.4 out of 10, Exceptional, (3 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.
The price is ￥47,592
￥53,672 total
includes taxes & fees
Mar 2 - Mar 3
Maho Beach Modern 1-Bedroom, Ocean Level
Property grounds

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 ￥47,708
￥63,143 total
includes taxes & fees
Mar 18 - Mar 19
Maho Beach House: Studio Getaway, Oceanfront Vibe
Property grounds

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
8.0 out of 10, Very Good, (1 review)
The price is ￥29,561
￥41,878 total
includes taxes & fees
Mar 17 - Mar 18
Maho Beach House Ocean Front Garden Studio
Pool

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
8.6 out of 10, Excellent, (4 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 ￥52,261
￥72,217 total
includes taxes & fees
Feb 26 - Feb 27
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Beach

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 ￥15,435
￥24,790 total
includes taxes & fees
Mar 8 - Mar 9
Beach Front Studio C3
Pool

Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
10.0 out of 10, Exceptional, (1 review)
"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 ￥31,395
￥35,985 total
includes taxes & fees
Feb 27 - Feb 28
Blue Sail Apartments - Two bedroom apartments
Beach

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
The price is ￥19,504
￥29,482 total
includes taxes & fees
Mar 8 - Mar 9
Beach Front 1 Bedroom Flat D3
On the beach, sun loungers, beach umbrellas, beach towels

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, (1,183 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
The price is ￥67,203
￥74,656 total
includes taxes & fees
Mar 15 - Mar 16
Hilton Vacation Club Royal Palm St. Maarten
Property grounds

Maho Beach House: Elegant 1-Bedroom, Beach Level

Maho Beach House: Elegant 1-Bedroom, Beach Level
Simpson Bay
The price is ￥41,909
￥55,161 total
includes taxes & fees
Mar 17 - Mar 18
Maho Beach House: Elegant 1-Bedroom, Beach Level
A heated pool

B242 - Glorious Lagoon View Apartment with Balcony

B242 - Glorious Lagoon View Apartment with Balcony
Sint Maarten
The price is ￥39,124
￥61,357 total
includes taxes & fees
Mar 19 - Mar 20
B242 - Glorious Lagoon View Apartment with Balcony
Interior

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 ￥43,967
￥57,531 total
includes taxes & fees
Mar 2 - Mar 3
Maho Beach Escape; Sunset Ocean View
Pool

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 ￥62,208
￥83,412 total
includes taxes & fees
Mar 14 - Mar 15
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Property grounds

Maho Beach House: Sand Bar Suite, 2-Bedroom

Maho Beach House: Sand Bar Suite, 2-Bedroom
Maho, Sint Maarten
The price is ￥83,069
￥107,391 total
includes taxes & fees
Mar 18 - Mar 19
Maho Beach House: Sand Bar Suite, 2-Bedroom
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is ￥97,288
￥123,169 total
includes taxes & fees
Mar 3 - Mar 4
Maho Beach Suite
WiFi, bed sheets

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.
The price is ￥13,876
￥21,672 total
includes taxes & fees
Feb 28 - Mar 1
Seafront Studio C4
Pool

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is ￥29,375
￥33,598 total
includes taxes & fees
Mar 22 - Mar 23
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

The Morgan Resort Spa Village

The Morgan Resort Spa Village

10/10 Excellent
"The room was great, beautiful view of the pool and ocean. Everything we the ate at the resort was great, the staff were also great. Would definitely stay here again :) Loved the little touches, like a rum punch and a hand/face towel when you check in."
Sabrina Cheng 5-night trip
Posted 3 days ago
The Morgan Resort Spa Village

Find out more about Simpson Bay

Search for holiday rentals in Simpson Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpson Bay using one of the methods below:

  • View our selection of featured holiday rentals in Simpson Bay
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  • Enter your travel dates to view the best deals on holiday rentals in Simpson Bay while they last

Look no further and take a look at our great range of rental properties in Simpson Bay!

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?

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 Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and White Sands Retreat - Beachside at Beacon Hill.

How many vacation rentals are there in Simpson Bay?

With 34 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.