Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Simpson Bay

Outdoor pool, sun loungers
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, (1156)
"Beautiful vacation "
Canada
alonzo
$214 nightly
The price is $225
Dec 4 - Dec 5
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites

Simpson Bay Suites

3.5 star property
Simpson Bay
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
$130 nightly
The price is $136
Dec 3 - Dec 4
Total with taxes and fees
Simpson Bay Suites
Amazing Top Floor Apartment | Balcony
The Hills Residence

The Hills Residence

3.0 star property
Simpson Bay
8.8 out of 10, Excellent, (51)
"Enjoyed my stay "
United States
Shakia
$254 nightly
The price is $266
Dec 8 - Dec 9
Total with taxes and fees
The Hills Residence
Smart TV, stereo, offices
Marina Views in the Heart of Simpson Bay

Marina Views in the Heart of Simpson Bay

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.
$326 nightly
The price is $340
Dec 3 - Dec 4
Total with taxes and fees
Marina Views in the Heart of Simpson Bay
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, (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.
$231 nightly
The price is $237
Dec 3 - Dec 4
Total with taxes and fees
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
Outdoor dining
D407 – Charming Apartment with Terrace

D407 – Charming Apartment with Terrace

Sint Maarten
$292 nightly
The price is $308
Dec 17 - Dec 18
Total with taxes and fees
D407 – Charming Apartment with Terrace
Pool
Charming 3BR Villa w Private Pool in Pelican Key

Charming 3BR Villa w Private Pool in Pelican Key

Pelican Key
$601 nightly
The price is $654
Dec 3 - Dec 4
Total with taxes and fees
Charming 3BR Villa w Private Pool in Pelican Key
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, (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.
$632 nightly
The price is $632
Dec 3 - Dec 4
Total with taxes and fees
Turquoise paradise, directly ON beach, gated w underground parking!
Exterior
Oceanview Escape in Sint Maarten

Oceanview Escape in Sint Maarten

Pelican Key
$554 nightly
The price is $578
Dec 5 - Dec 6
Total with taxes and fees
Oceanview Escape in Sint Maarten
On the beach
Maho Beach Escape; Sunset Ocean View

Maho Beach Escape; Sunset Ocean View

Maho, Sint Maarten
10.0 out of 10, Exceptional, (4)
"Self check in and out was a nice experience "
United States
Kelva
$256 nightly
The price is $256
Dec 3 - Dec 4
Total with taxes and fees
Maho Beach Escape; Sunset Ocean View
Pool
Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Simpson Bay
$508 nightly
The price is $530
Dec 3 - Dec 4
Total with taxes and fees
Beacon Hill Hideaway: Luxury Condo in Simpson Bay
TV
B251 - Beautiful 2 Bedroom with lagoon view

B251 - Beautiful 2 Bedroom with lagoon view

Sint Maarten
$346 nightly
The price is $365
Dec 5 - Dec 6
Total with taxes and fees
B251 - Beautiful 2 Bedroom with lagoon view
Exterior
Maho Oceanfront Luxe: Modern and Spacious Condo

Maho Oceanfront Luxe: Modern and Spacious Condo

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.
$229 nightly
The price is $229
Dec 3 - Dec 4
Total with taxes and fees
Maho Oceanfront Luxe: Modern and Spacious Condo
Living area
D438 – Amazing 2-Bedroom Lagoon View with Balcony

D438 – Amazing 2-Bedroom Lagoon View with Balcony

Sint Maarten
$624 nightly
The price is $666
Dec 25 - Dec 26
Total with taxes and fees
D438 – Amazing 2-Bedroom Lagoon View with Balcony
Pool
A116 - Immersive Simpson Bay Lagoon View

A116 - Immersive Simpson Bay Lagoon View

Sint Maarten
$283 nightly
The price is $298
Dec 17 - Dec 18
Total with taxes and fees
A116 - Immersive Simpson Bay Lagoon View
On the beach, sun loungers, beach towels
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

Simpson Bay
9.4 out of 10, Exceptional, (16)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
$784 nightly
The price is $814
Dec 30 - Dec 31
Total with taxes and fees
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Property grounds
Caribbean Sea Studio next to The Morgan Resort

Caribbean Sea Studio next to The Morgan Resort

Maho, Sint Maarten
8.0 out of 10, Very Good, (1)
$237 nightly
The price is $237
Dec 3 - Dec 4
Total with taxes and fees
Caribbean Sea Studio next to The Morgan Resort
Pool
A111 - Condo with amazing view

A111 - Condo with amazing view

Sint Maarten
$406 nightly
The price is $431
Dec 23 - Dec 24
Total with taxes and fees
A111 - Condo with amazing view
Pool
A102 - Cozy Apartment with Garden

A102 - Cozy Apartment with Garden

Sint Maarten
$348 nightly
The price is $369
Dec 29 - Dec 30
Total with taxes and fees
A102 - Cozy Apartment with Garden
Property grounds
Maho Beach House: Elegant 1-Bedroom, Beach Level

Maho Beach House: Elegant 1-Bedroom, Beach Level

Simpson Bay
$295 nightly
The price is $295
Dec 3 - Dec 4
Total with taxes and fees
Maho Beach House: Elegant 1-Bedroom, Beach Level
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
"Nice rooms with excellent air conditioning! Pool area and restaurant is exceptional. Friendly staff and a very convenient location. Fun to watch the planes come in from the infinity pool! "
Dean 1-night trip
Posted 4 days ago
The Morgan Resort Spa Village

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
This month
Next month
November
January
$424
$429
Month
Price
January
$429
February
$402
March
$420
April
$380
May
$278
June
$282
July
$283
August
$246
September
$211
October
$200
November
$169
December
$424
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 $66 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.

Explore a world of travel with Expedia

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.