Simpson Bay Vacation Rentals

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Check prices for these dates

Tonight
Nov 28 - Nov 29
Tomorrow
Nov 29 - Nov 30
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Vacation Rentals in Simpson Bay

Outdoor pool, sun loungers
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Simpson Bay

4.0 star property
9.0 out of 10, Wonderful, (1155)
"Beautiful vacation "
Canada
alonzo
The price is ￥21,232
￥26,397 total
includes taxes & fees
Dec 17 - Dec 18
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony
The Hills Residence

Aparthotel in Simpson Bay

3.0 star property
8.8 out of 10, Excellent, (50)
"This apartment was nice, clean, modern, walking distance to restaurants and shops. "
United States
Lionel
The Hills Residence
Pool
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Apartment in Simpson Bay

10.0 out of 10, Exceptional, (1)
"Communication with the host was very easy. The location is outstanding and the facility has every amenity. You can imagine. I highly recommend this property and can’t wait to visit again."
United States
Richard S.
The price is ￥19,763
￥37,000 total
includes taxes & fees
Nov 29 - Nov 30
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites

Aparthotel in Simpson Bay

3.5 star property
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
The price is ￥18,989
￥21,269 total
includes taxes & fees
Dec 1 - Dec 2
Simpson Bay Suites
Smart TV, stereo, offices
Marina Views in the Heart of Simpson Bay

Apartment in Simpson Bay

10.0 out of 10, Exceptional, (1)
"We loved this place so much we bought it! The location is to die for. Right in the heart of Simpson Bay, there is soooo much to see and do right around you. The beach is literally a four minute walk and the water is calm and beautiful. We can’t wait to come back again and again! Also, Kayla, the manager is the best to work with. Sweet and helpful."
United States
Trish S.
The price is ￥28,914
￥57,734 total
includes taxes & fees
Nov 30 - Dec 1
Marina Views in the Heart of Simpson Bay
Exterior
Maho Oceanfront Luxe: Modern and Spacious Condo

Condo in Maho

9.4 out of 10, Exceptional, (3)
"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 ￥28,451
￥32,515 total
includes taxes & fees
Dec 2 - Dec 3
Maho Oceanfront Luxe: Modern and Spacious Condo
Property grounds
Turquoise paradise, directly ON beach, gated w underground parking!

Apartment in Simpson Bay

9.8 out of 10, Exceptional, (20)
"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 ￥61,735
￥81,115 total
includes taxes & fees
Nov 29 - Nov 30
Turquoise paradise, directly ON beach, gated w underground parking!
Property grounds
Maho Beach House: Studio Getaway, Oceanfront Vibe

Condo in Maho, Sint Maarten

10.0 out of 10, Exceptional, (2)
"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.
Maho Beach House: Studio Getaway, Oceanfront Vibe
TV
A117 - Lovely 2 Bedroom with Lagoon View

Apartment in Sint Maarten

2.0 star property
The price is ￥35,040
￥53,795 total
includes taxes & fees
Dec 2 - Dec 3
A117 - Lovely 2 Bedroom with Lagoon View
Pool
A116 - Immersive Simpson Bay Lagoon View

Apartment in Sint Maarten

A116 - Immersive Simpson Bay Lagoon View
Outdoor dining
D407 – Charming Apartment with Terrace

Apartment in Sint Maarten

D407 – Charming Apartment with Terrace
Exterior
Oceanview Escape in Sint Maarten

Condo in Pelican Key

The price is ￥39,541
￥93,030 total
includes taxes & fees
Dec 9 - Dec 10
Oceanview Escape in Sint Maarten
Pool
A101 - Outstanding Lagoon View & Garden

Apartment in Sint Maarten

The price is ￥30,555
￥50,966 total
includes taxes & fees
Dec 2 - Dec 3
A101 - Outstanding Lagoon View & Garden
Pool
Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Condo in Simpson Bay

The price is ￥49,869
￥96,571 total
includes taxes & fees
Dec 3 - Dec 4
Beacon Hill Hideaway: Luxury Condo in Simpson Bay
Property grounds
Maho Beach House: Elegant 1-Bedroom, Beach Level

Condo in Simpson Bay

The price is ￥34,509
￥46,856 total
includes taxes & fees
Dec 2 - Dec 3
Maho Beach House: Elegant 1-Bedroom, Beach Level
Pool
Sunny Days at Simpson Bay Yacht Club

Condo in Simpson Bay

10.0 out of 10, Exceptional, (2)
"This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again"
United States
JEROME J.
The price is ￥51,263
￥89,123 total
includes taxes & fees
Dec 1 - Dec 2
Sunny Days at Simpson Bay Yacht Club
Pool
Charming 3BR Villa w Private Pool in Pelican Key

Vacation Home in Pelican Key

The price is ￥43,936
￥104,197 total
includes taxes & fees
Dec 1 - Dec 2
Charming 3BR Villa w Private Pool in Pelican Key
Pool
A111 - Condo with amazing view

Apartment in Sint Maarten

The price is ￥44,018
￥67,353 total
includes taxes & fees
Dec 23 - Dec 24
A111 - Condo with amazing view
On the beach
Maho Beach Escape; Sunset Ocean View

Condo in Maho, Sint Maarten

10.0 out of 10, Exceptional, (4)
"Self check in and out was a nice experience "
United States
Kelva
The price is ￥27,382
￥39,416 total
includes taxes & fees
Dec 2 - Dec 3
Maho Beach Escape; Sunset Ocean View
Property grounds
Maho Beach House: Sunset Suite, 1-Bedroom

Condo in Maho

10.0 out of 10, Exceptional, (1)
"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.
The price is ￥33,384
￥47,450 total
includes taxes & fees
Dec 2 - Dec 3
Maho Beach House: Sunset Suite, 1-Bedroom
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 Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"I want to see the place first and I wasn't disappointed here.i would recommend this hotel fto ay"
Nadia 4-night trip
Posted 2 days ago
The Villas at Simpson Bay Resort

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
  • Use the map to find apartments and other holiday homes in the Simpson Bay neighbourhood you prefer
  • 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 top-notch restaurants and lively bars.

What are some of the best vacation home rentals that Simpson Bay has to offer?

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Charming 3BR Villa w Private Pool in Pelican Key.

How many vacation rentals are there in Simpson Bay?

With 36 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 Orient 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.