Simpson Bay Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Tonight
Jan 15 - Jan 16
Tomorrow
Jan 16 - Jan 17
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

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
8.4 out of 10, Very Good, (68 reviews)
"Three guests, paid extra for third. Messaged reminder to hotel that we needed couch bed to have bedding. Arrival= no bedding or pillows and one towel and one shower gel for three people. Absolutely disappointing, requested bedding and pillows three times. Finally ONLY sheets show up. No blanket or pillows. Go all the way down a big long ramp to request again. To be told will send. Never came. 4th time said hotel doesn’t have any???? Most ridiculous hotel, next to zero service, no cleaning nor...
Canada
Phillip
$311 nightly
The price is $325
Feb 2 - Feb 3
Total with taxes and fees
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, (131 reviews)
"It is 'value priced', has a convenient location and the AC works :) But be realistic in your expectations, this is not competing with the Hiltons and Morgans on the island. Great for an overnight layover. Huge rooms - Really it's a full sized apartment with all the amenities. "
United States
Roger
$181 nightly
The price is $189
Jan 16 - Jan 17
Total with taxes and fees
Simpson Bay Suites
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, (1,171 reviews)
"Room was great, resort was great, staff was great"
Canada
Gisele
$427 nightly
The price is $449
Feb 12 - Feb 13
Total with taxes and fees
Hilton Vacation Club Royal Palm St. Maarten
Iron/ironing board, free WiFi

MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
6.2 out of 10, (10 reviews)
"The room was very clean and tidy. The staff were very helpful. Request for taxi service to the airport waited for over an hour. With the help of a neighbor a taxi was flagged down "
United States
Carol
$86 nightly
The price is $90
Jan 17 - Jan 18
Total with taxes and fees
MIDTOWN MOTEL SXM
Deluxe Double Room | Down comforters, free WiFi, bed sheets

July Apartments

July Apartments
3.0 star property
Madame's Estate
9.2 out of 10, Wonderful, (166 reviews)
"Room was clean. Staff was friendly. Location was close to shopping and restaurant with a taxi. "
United States
DANICA
$77 nightly
The price is $80
Jan 19 - Jan 20
Total with taxes and fees
July Apartments
Outdoor pool

Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.6 out of 10, Excellent, (24 reviews)
"Very clean , beautiful pool , great food at the restaurant pool side , amazing service by everyone especially Ramon and Serge !! Such a pleasure to be around them ! Coffee shop was also great ! A beautiful Place for a family or a couples getaway ! "
Canada
Melissa
$686 nightly
The price is $717
Jan 24 - Jan 25
Total with taxes and fees
Dawn Beach Club Resort Sint Maarten
702: Grand Apartment, 1 Queen Bed, Balcony, Sea View | Living area | 55-inch Smart TV with satellite channels, Netflix, Hulu

Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.8 out of 10, Exceptional, (123 reviews)
"Staff was courteous but we got a notifications that the breakfast that is included with our stay is not available on Sundays"
United States
KATPADY
$310 nightly
The price is $325
Jan 20 - Jan 21
Total with taxes and fees
Mullet Bay Suites: Your Luxury Stay Awaits
Outdoor pool

condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-
4.0 star property
Indigo Bay
9.2 out of 10, Wonderful, (25 reviews)
"Good location easy access to a private beach "
United States
All About
$495 nightly
The price is $516
Jan 20 - Jan 21
Total with taxes and fees
condostmaarten by the sea -Adults Only-
Terrace/patio

The Forest

The Forest
4.0 star property
Anse Marcel
10.0 out of 10, Exceptional, (17 reviews)
"An oasis in the hills above Anse Marcel. Lovely property, beautiful rooms, great food and warm, welcoming hosts!"
United States
Daniel
$431 nightly
The price is $450
Jan 19 - Jan 20
Total with taxes and fees
The Forest
Villa | Living area

Avenue du lagon

Avenue du lagon
Oyster Pond
$1,883 nightly
The price is $1,958
Feb 10 - Feb 11
Total with taxes and fees
Avenue du lagon
Exterior

Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
$527 nightly
The price is $550
Jan 16 - Jan 17
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.2
Beach

Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
$527 nightly
The price is $550
Jan 16 - Jan 17
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.1
Beach

Singh Luxury Apartments With sea View, Apt.3

Singh Luxury Apartments With sea View, Apt.3
3.0 star property
Oyster Pond
2.0 out of 10, (1 review)
$914 nightly
The price is $956
Jan 16 - Jan 17
Total with taxes and fees
Singh Luxury Apartments With sea View, Apt.3
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

Commodore Suites

Commodore Suites

10/10 Excellent
"Great amenities"
Dale 3-night trip
Posted 2 days ago
Commodore Suites

Price trends for vacation rentals in Simpson Bay

Less expensive
More expensive
Next month
October
March
$390
Month
Price
January
$384
February
$390
March
$402
April
$378
May
$299
June
$285
July
$304
August
$287
September
$267
October
$262
November
$280
December
$366
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 $159 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?

Charming 3BR Villa w Private Pool in Pelican Key: Visitors like this Simpson Bay vacation home rental. It offers a balcony, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Simpson Bay are White Sands Retreat - Beachside at Beacon Hill and Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 37 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.