Photo by Dorothy Schmidt

Holiday Rentals in Simpson Bay

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Our top choices for Simpson Bay holiday rentals

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 €163
includes taxes & fees
12 Jan - 13 Jan
Simpson Bay Suites

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
4.0 star property
9.0 out of 10, Wonderful, (1,170 reviews)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is €368
includes taxes & fees
15 Jan - 16 Jan
Hilton Vacation Club Royal Palm St. Maarten
10.0 out of 10, Exceptional, (2 reviews)
"perfect!!"
United States
jason l.
The price is €284
includes taxes & fees
13 Jan - 14 Jan
1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)
2.0 star property
Modern 2BR Villa | Beach Access | Mins to Maho
10.0 out of 10, Exceptional, (1 review)
"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 €430
includes taxes & fees
19 Jan - 20 Jan
Marina Views in the Heart of Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is €360
includes taxes & fees
2 Feb - 3 Feb
Maho Beach House: Studio Getaway, Oceanfront Vibe

Apartment in Sint Maarten

A115 - Incredible Lagoon View
A115 - Incredible Lagoon View
9.4 out of 10, Exceptional, (3 reviews)
"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 €287
includes taxes & fees
13 Jan - 14 Jan
Maho Beach Modern 1-Bedroom, Ocean Level
B237 - Cosy 1 Bedroom with Lagoon View
A101 - Outstanding Lagoon View & Garden
A103 - Incredible Apartment with Garden
9.4 out of 10, Exceptional, (16 reviews)
"Great location close to everything I will definitely be back love it."
United States
keenan j.
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
2.0 star property
The price is €750
includes taxes & fees
9 Feb - 10 Feb
Modern 2BR Townhome | Walk to Maho & SXM Planes
9.8 out of 10, Exceptional, (21 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 €656
includes taxes & fees
12 Jan - 13 Jan
Turquoise paradise, directly ON beach, gated w underground parking!
2.0 star property
Maho Beach 3BR Villa | Huge Terrace & Runway View
The price is €712
includes taxes & fees
28 Jan - 29 Jan
Beacon Hill Hideaway: Luxury Condo in Simpson Bay
10.0 out of 10, Exceptional, (2 reviews)
"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.
Sunny Days at Simpson Bay Yacht Club
The price is €743
includes taxes & fees
13 Jan - 14 Jan
Charming 3BR Villa w Private Pool in Pelican Key
The price is €491
includes taxes & fees
7 Feb - 8 Feb
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
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, apart-hotels, 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 favorite 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 depends 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 €163 per night. Entering your travel dates in the search wizard you might find 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.