Holiday Rentals in Simpson Bay

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Our top choices for Simpson Bay holiday rentals

Aparthotel in Simpson Bay

The Hills Residence
3.0 star property
8.6 out of 10, Excellent, (89 reviews)
"Great staff, would stay again!"
United States
Maimuna
The Hills Residence

Aparthotel in Simpson Bay

Simpson Bay Suites
3.5 star property
7.0 out of 10, Good, (137 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
The price is €160
includes taxes & fees
21 Mar - 22 Mar
Simpson Bay Suites
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 €293
includes taxes & fees
2 Mar - 3 Mar
Maho Beach Modern 1-Bedroom, Ocean Level
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 €345
includes taxes & fees
18 Mar - 19 Mar
Maho Beach House: Studio Getaway, Oceanfront Vibe

Apartment in Maho, Sint Maarten

Maho Beach House Ocean Front Garden Studio
8.0 out of 10, Very good, (1 review)
The price is €252
includes taxes & fees
17 Mar - 18 Mar
Maho Beach House Ocean Front Garden Studio
8.4 out of 10, Very good, (5 reviews)
"Very good place. Service very good. Keep up the good work lisa"
United States
Carlos
The price is €447
includes taxes & fees
5 Mar - 6 Mar
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Apartment in Simpson Bay

Beach Front Studio C3
8.8 out of 10, Excellent, (3 reviews)
"Clean and modern. Need a door for the bathroom. Check in was easy and Lisa was there to help us get checked in. She even provided 2 cold water and 2 cold beers"
United States
Norman
Beach Front Studio C3
10.0 out of 10, Exceptional, (1 review)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
Blue Sail Apartments - Two bedroom apartments

Apartment in Simpson Bay

Beach Front 1 Bedroom Flat D3
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
The price is €161
includes taxes & fees
8 Mar - 9 Mar
Beach Front 1 Bedroom Flat D3
4.0 star property
9.0 out of 10, Wonderful, (1,184 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
The price is €405
includes taxes & fees
15 Mar - 16 Mar
Hilton Vacation Club Royal Palm St. Maarten
The price is €301
includes taxes & fees
17 Mar - 18 Mar
Maho Beach House: Elegant 1-Bedroom, Beach Level
B242 - Glorious Lagoon View Apartment with Balcony

Condo in Maho, Sint Maarten

Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, (4 reviews)
"Self check in and out was a nice experience "
United States
Kelva
The price is €313
includes taxes & fees
2 Mar - 3 Mar
Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, (1 review)
"Incredible property. Views for days, great location. Had a wonderful stay and Lisa was great also. Very secure condo and clean. Loved the pool and so many dining options close by. "
United States
Camelo
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
The price is €585
includes taxes & fees
18 Mar - 19 Mar
Maho Beach House: Sand Bar Suite, 2-Bedroom

Condo in Simpson Bay

Maho Beach Suite
The price is €673
includes taxes & fees
3 Mar - 4 Mar
Maho Beach Suite

Apartment in Simpson Bay

Seafront Studio C4
10.0 out of 10, Exceptional, (3 reviews)
"My stay was amazing. Room was nice and cozy, located on strip near buccaneer beach. Everything was walking distance and the host was very kind and helpful and even gave me a gift. I traveled alone and felt extremely safe at this property. I will be returning!!"
United States
sacoya f.
Seafront Studio C4
The price is €182
includes taxes & fees
22 Mar - 23 Mar
Blue Sail Apartments - 1 bedroom apartments
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 €160 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 lively bars and top-notch restaurants.

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

Philips Scott House Calinago: This holiday home rental outside Simpson Bay is in a shopping district, and equipped with air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities such as a microwave and free parking are also available for your convenience. Some other homes for rent in Simpson Bay include Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and White Sands Retreat - Beachside at Beacon Hill.

How many holiday rentals are there in Simpson Bay?

With 34 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.