Simpson Bay Holiday Rentals

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Our top choices for Simpson Bay holiday rentals

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.4 out of 10, Very good, (68 reviews)
"Good location, walkable area, great views. "
United States
Tiffany
The Hills Residence

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
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
The price is AU$283
includes taxes & fees
21 Jan - 22 Jan
Simpson Bay Suites
4.0 star property
9.0 out of 10, Wonderful, (1,171 reviews)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is AU$671
includes taxes & fees
12 Feb - 13 Feb
Hilton Vacation Club Royal Palm St. Maarten

Aparthotel in Downtown Philipsburg

MIDTOWN MOTEL SXM
2.5 star property
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
The price is AU$134
includes taxes & fees
20 Jan - 21 Jan
MIDTOWN MOTEL SXM

Aparthotel in Madame's Estate

July Apartments
3.0 star property
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
July Apartments

Condo resort in Oyster Pond

Dawn Beach Club Resort Sint Maarten
4.0 star property
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
Dawn Beach Club Resort Sint Maarten
4.0 star property
9.8 out of 10, Exceptional, (123 reviews)
"Great apartment and great location!"
United States
Miljan
The price is AU$563
includes taxes & fees
2 Feb - 3 Feb
Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
9.2 out of 10, Wonderful, (25 reviews)
"Good location easy access to a private beach "
United States
All About
The price is AU$772
includes taxes & fees
21 Jan - 22 Jan
condostmaarten by the sea -Adults Only-

Aparthotel in Anse Marcel

The Forest
4.0 star property
10.0 out of 10, Exceptional, (17 reviews)
"This is a wonderful property to stay at we loved it and really wish we never had to leave but alas real life must go on "
United States
Mitchel
The price is AU$672
includes taxes & fees
20 Jan - 21 Jan
The Forest

Villa in Oyster Pond

Avenue du lagon
The price is AU$2,930
includes taxes & fees
10 Feb - 11 Feb
Avenue du lagon
3.5 star property
The price is AU$823
includes taxes & fees
24 Jan - 25 Jan
Singh Luxury Apartments With sea View, Apt.2
3.0 star property
The price is AU$823
includes taxes & fees
17 Jan - 18 Jan
Singh Luxury Apartments With sea View, Apt.1
3.0 star property
2.0 out of 10, (1 review)
The price is AU$1,431
includes taxes & fees
16 Jan - 17 Jan
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.
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Top Simpson Bay Hotel Reviews

Find out more about Simpson Bay

Everything you need to know about Simpson Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Simpson Bay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay holiday rentals we have selected for you start as low as AU$241 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Simpson Bay has to offer?

Charming 3BR Villa w Private Pool in Pelican Key: This highly rated holiday home rental in Simpson Bay offers a balcony, a selection of games and a BBQ 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 that you can cook with friends or family. Other favourite 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 holiday rentals are there in Simpson Bay?

With 37 Expedia holiday rentals, you're guaranteed 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 holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.