A wooden pier extending into calm waters with sailboats anchored nearby.

Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Simpson Bay vacation rentals

Terrace/patio

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (159 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 ￥19,712
￥22,079 total
includes taxes & fees
Jul 22 - Jul 23
Simpson Bay Suites
Amazing Top Floor Apartment | Balcony

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very Good, (158 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is ￥27,481
￥46,169 total
includes taxes & fees
Jul 22 - Jul 23
The Hills Residence
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, (1,250 reviews)
"Great staff.. Great location..Great property"
United States
Wilbert
The price is ￥36,212
￥42,282 total
includes taxes & fees
Aug 15 - Aug 16
Hilton Vacation Club Royal Palm St. Maarten
Property grounds

Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is ￥16,639
￥19,967 total
includes taxes & fees
Jul 16 - Jul 17
Blue Sail Apartments - Double room
Property grounds

Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
The price is ￥29,203
￥41,695 total
includes taxes & fees
Jul 16 - Jul 17
Maho Beach House - Petit Studio Océanique - Charmante Vue
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 ￥59,782
￥82,200 total
includes taxes & fees
Jul 16 - Jul 17
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Property grounds

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 ￥64,085
￥85,338 total
includes taxes & fees
Jul 16 - Jul 17
Turquoise paradise, directly ON beach, gated w underground parking!
Interior

Maho Beach Suite

Maho Beach Suite
Simpson Bay
The price is ￥60,431
￥83,012 total
includes taxes & fees
Aug 2 - Aug 3
Maho Beach Suite
Beach

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
8.8 out of 10, Excellent, (5 reviews)
"Really cool place and the location was prime. The cleaning lady was the nicest person there could be as well. "
Canada
Benjamin
The price is ￥16,083
￥25,830 total
includes taxes & fees
Jul 16 - Jul 17
Beach Front Studio C3
Beach

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 ￥20,322
￥30,556 total
includes taxes & fees
Jul 16 - Jul 17
Beach Front 1 Bedroom Flat D3
TV

B225 - Incredible Lagoon View

B225 - Incredible Lagoon View
Sint Maarten
The price is ￥29,674
￥57,815 total
includes taxes & fees
Jul 16 - Jul 17
B225 - Incredible Lagoon View
Pool

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 ￥17,748
￥35,205 total
includes taxes & fees
Jul 28 - Jul 29
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Pool

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Simpson Bay
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
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
8.8 out of 10, Excellent, (6 reviews)
The price is ￥47,825
￥68,619 total
includes taxes & fees
Jul 16 - Jul 17
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Outdoor dining

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 ￥19,967
￥23,295 total
includes taxes & fees
Jul 16 - Jul 17
Blue Sail Apartments - Two bedroom apartments
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 ￥33,140
￥46,298 total
includes taxes & fees
Jul 23 - Jul 24
Maho Beach Escape; Sunset Ocean View
Outdoor dining

Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is ￥28,286
￥32,168 total
includes taxes & fees
Jul 16 - Jul 17
Blue Sail Apartments - 1 bedroom apartments
Pool

Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!

Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
Simpson Bay
10.0 out of 10, Exceptional, (4 reviews)
"Location worked out well close to airport. We were able to walk to beach and restaurants "
United States
Dominick C.
The price is ￥100,557
￥142,794 total
includes taxes & fees
Jul 27 - Jul 28
Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
Pool

Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!

Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!
Simpson Bay
2.0 out of 10, (1 review)
The price is ￥108,052
￥150,072 total
includes taxes & fees
Aug 12 - Aug 13
Beach Front 4 Bed Condon D2.1 with Sea View and Private Pool !!
Beach

To complete

To complete
Cul-de-Sac
The price is ￥10,168
￥11,092 total
includes taxes & fees
Jul 16 - Jul 17
To complete
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
"Great stay"
Chasity 3-night trip
Posted less than an hour 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:

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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 New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 46 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. In the larger area, you’ll find popular places like Maho Beach and Mullet Bay Beach.

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.