Simpson Bay Holiday Rentals

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Our top choices for Simpson Bay holiday rentals

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (133 reviews)
"Room was clean. Had a full living room and kitchen incl microwave. Convenient to kim-sha beach. "
United States
Dale
The price is NZ$314
includes taxes & fees
17 Mar - 18 Mar
Simpson Bay Suites

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, (1,179 reviews)
"Great staff, location and amenities."
United States
Deon Oliver
The price is NZ$826
includes taxes & fees
20 Feb - 21 Feb
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (82 reviews)
"Great staff, would stay again!"
United States
Maimuna
The Hills Residence

Charming 3BR Villa w Private Pool in Pelican Key

Charming 3BR Villa w Private Pool in Pelican Key
Pelican Key
Charming 3BR Villa w Private Pool in Pelican Key

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
Simpson Bay
The price is NZ$878
includes taxes & fees
14 Mar - 15 Mar
Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach Modern 1-Bedroom, Ocean Level
Maho
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 NZ$579
includes taxes & fees
9 Mar - 10 Mar
Maho Beach Modern 1-Bedroom, Ocean Level

Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
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 NZ$881
includes taxes & fees
19 Feb - 20 Feb
Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House Ocean Front Garden Studio

Maho Beach House Ocean Front Garden Studio
Maho, Sint Maarten
8.0 out of 10, Very good, (1 review)
The price is NZ$448
includes taxes & fees
17 Mar - 18 Mar
Maho Beach House Ocean Front Garden Studio

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Beacon Hill Hideaway: Luxury Condo in Simpson Bay
Simpson Bay
The price is NZ$1,288
includes taxes & fees
2 Mar - 3 Mar
Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Beach Front 1 Bedroom Flat D3

Beach Front 1 Bedroom Flat D3
Simpson Bay
10.0 out of 10, Exceptional, (1 review)
"Great spot! Clean, comfortable and well equipped. "
United States
Jill
The price is NZ$330
includes taxes & fees
17 Mar - 18 Mar
Beach Front 1 Bedroom Flat D3

Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
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

Beach Front Studio C3

Beach Front Studio C3
Simpson Bay
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
The price is NZ$263
includes taxes & fees
17 Mar - 18 Mar
Beach Front Studio C3

D408 – Chic & Stylish 2 Bedroom with Terrace

D408 – Chic & Stylish 2 Bedroom with Terrace
Sint Maarten
The price is NZ$904
includes taxes & fees
16 Feb - 17 Feb
D408 – Chic & Stylish 2 Bedroom with Terrace

C337 - Charming 2-Bedroom Lagoon View

C337 - Charming 2-Bedroom Lagoon View
Sint Maarten
The price is NZ$869
includes taxes & fees
18 Feb - 19 Feb
C337 - Charming 2-Bedroom Lagoon View

A101 - Outstanding Lagoon View & Garden

A101 - Outstanding Lagoon View & Garden
Sint Maarten
A101 - Outstanding Lagoon View & Garden

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)
Simpson Bay
The price is NZ$523
includes taxes & fees
18 Feb - 19 Feb
Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

B256 - Amazing Top Floor Apartment With Balcony

B256 - Amazing Top Floor Apartment With Balcony
Sint Maarten
B256 - Amazing Top Floor Apartment With Balcony

Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
Simpson Bay
8.6 out of 10, Excellent, (4 reviews)
"Great place to stay with a lot of privacy and walkable to stores and restaurants. Amazing views! Lisa is so friendly and keeps the place amazing!"
United States
Alaciel S.
The price is NZ$759
includes taxes & fees
17 Feb - 18 Feb
Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.0 out of 10, Wonderful, (2 reviews)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
The price is NZ$631
includes taxes & fees
23 Feb - 24 Feb
Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach Escape; Sunset Ocean View

Maho Beach Escape; Sunset Ocean View
Maho, Sint Maarten
10.0 out of 10, Exceptional, (4 reviews)
"Self check in and out was a nice experience "
United States
Kelva
The price is NZ$828
includes taxes & fees
21 Feb - 22 Feb
Maho Beach Escape; Sunset Ocean View
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 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 NZ$263 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?

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : This highly rated holiday home rental in Simpson Bay is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 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 New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove.

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.