Simpson Bay Vacation Rentals

Vacation Rentals in Simpson Bay

Orchid | View from room
The Horny Toad Guesthouse
3.0 star property
9.4 out of 10, Exceptional, (51)
"Deb & Doug are accommodating and great to talk to to get ideas of things to do. Perfect place to stay!"
The price is $172
$222 total
includes taxes & fees
May 29 - May 30
The Horny Toad Guesthouse
Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
10.0 out of 10, Exceptional, (66)
""We had an incredible stay at Villa Namaste! The property is gorgeous, with every room beautifully appointed. The view from the patio is breathtaking—worth every penny. Sitting in the infinity edge pool, looking out over the bluest Caribbean waters while watching mega yachts sail by, was a highlight of our days. The villa is also conveniently located close to many cool restaurants, some even within walking distance, which was perfect for our evenings out. The staff, particularly Olive and...
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites
3.5 star property
6.8 out of 10, (100)
"Convenient location with the requisite amenities for local stay and business. Water pressure could be improved. Though clean and tidy furniture could be modernized. "
The price is $122
$136 total
includes taxes & fees
May 29 - May 30
Simpson Bay Suites
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Exterior
Tradewinds at Simpson Bay
3.5 star property
8.6 out of 10, Excellent, (10)
"The room was spacious and spotless . The staff were attentive and went out of their way to ensure that we were comfortable. Nothing was too much trouble.Will be back excellent stay "
Tradewinds at Simpson Bay
Beach | On the beach, sun loungers, beach towels
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
10.0 out of 10, Exceptional, (24)
"Our family of 5 (2-10yr old boys, 1-14yr old girl) were very pleased with the condo. The location was prime in Simpson Bay. Within walking distance to a few beach bars and walked over to Maho Beach too a few times. The pool was nice (warm) and had plenty of seating, always a few seats available. There are beach chairs, toys on the porch along with a beach umbrella. The kitchen was well equipped and left us not needing anything. Bath linens could use a refresh but was sufficient. The only...
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Outdoor pool
Oceanfront amazing 2 bedrooms Condo
9.8 out of 10, Exceptional, (49)
"The condo was very nice. The furnishings were as expected and very tastefully done. The only detractor was the cleanliness of the pool. It needs more attention than what it currently receives and it is full sun. There is no shaded area if you’re hoping to take a break from the sun."
Oceanfront amazing 2 bedrooms Condo
Property grounds
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
9.6 out of 10, Exceptional, (71)
"Beautiful building, property, and very spacious condo with great views. Highly recommended."
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
Outdoor pool
BEACHFRONT DESIGN VILLA
9.8 out of 10, Exceptional, (111)
"Stacey was great and set up our excursions which were great. House was perfect!"
BEACHFRONT DESIGN VILLA
Pool
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
10.0 out of 10, Exceptional, (80)
"As advertised. There is a security guard shack steps from the property which is manned 6 pm - 6am."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Property grounds
Anchor House - Direct Oceanfront - Luxury & Modern Style
10.0 out of 10, Exceptional, (125)
"This property is simply stunning. Very clean. Safe area. Walkable to restaurants, bars, markets and the beach, however we did rent a car. Property manager Stacey was amazing. The pictures are spot on for this property and we are booking again in the coming months! I was a little worried that sometimes you aren’t sure what you are booking but this was amazingly perfect. Can’t wait to go back!"
Anchor House - Direct Oceanfront - Luxury & Modern Style
On the beach, beach bar
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
9.8 out of 10, Exceptional, (20)
"Nice property. Grounds and pool maintained. Stayed for 2 weeks. We do cook meals at least half the time and found the kitchen could use some necessities like cups and bowls. Also, living room furniture is lacking seating and current furniture is uncomfortable. Other than that it would be nice if each bedroom had a TV. We will return."
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
Property grounds
Top of the art penthouse on the beach - 4000 sq. ft of luxury
9.8 out of 10, Exceptional, (59)
"Well laid out property, centrally located on the ilsland wirh rhe bonus of being on the Simpson Bay beachfront."
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Outdoor pool
Oceanfront amazing 2 BR Villa - 2 min from the beach
9.6 out of 10, Exceptional, (91)
"We had a wonderful week in St Maarten at the Cliffside property overlooking Simpson Bay. Perfect for 2 couples with great outdoor spaces and views of the water on 2 sides. We will definitely be back!"
Oceanfront amazing 2 BR Villa - 2 min from the beach
Exterior
Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, (3)
"Self check in and out was a nice experience "
The price is $130
$199 total
includes taxes & fees
May 30 - May 31
Maho Beach Escape; Sunset Ocean View
On the beach, sun loungers, beach towels
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay over Easter weekend. The beach was busy."
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
On the beach, sun loungers, beach towels
White Sands Retreat - Beachside at Beacon Hill
9.0 out of 10, Wonderful, (25)
"Five minutes walk to the beach. Nice little house."
White Sands Retreat - Beachside at Beacon Hill
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio
Fourteen at Mullet Bay
3.5 star property
9.6 out of 10, Exceptional, (118)
"Beautiful and peaceful definitely going back"
Fourteen at Mullet Bay
Sundeck
Dawn Beach Club Resort Sint Maarten
4.0 star property
8.6 out of 10, Excellent, (14)
"Nice property, but far away from the airport and party area"
The price is $699
$839 total
includes taxes & fees
Jun 4 - Jun 5
Dawn Beach Club Resort Sint Maarten
Front of property
July Apartments
3.0 star property
9.2 out of 10, Wonderful, (71)
"The host was understanding and kind, they extended my checkout time so I could leave for my flight at an appropriate time."
The price is $68
$81 total
includes taxes & fees
Jun 11 - Jun 12
July Apartments
Sun loungers, beach towels
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
10.0 out of 10, Exceptional, (8)
"The house was just as listed and the area was perfect. We enjoyed our stay and would recommend and will return!"
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
Don't see what you're looking for?
See all available properties in Simpson Bay
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.

Simpson Bay Vacation Rental Travel Info

Number of vacation rentals
167
Popular accommodation
Simpson Bay villas
Known landmarks
Maho Beach, Mullet Bay Beach and Simpson Bay Beach
International airport
Philipsburg (SXM-Princess Juliana Intl.)

Other types of properties in Simpson Bay you may be interested in

Outdoor pool, sun loungers
The Morgan Resort Spa Village
4.0 star property
9.2 out of 10, Wonderful, (1230)
"Our second time at the resort, we visited about 18months ago. The service was not as great as the first time and found some of the amenities lacking -like towel shortage. Check in was after 4pm as rooms not ready. Pool area loungers and umbrellas starting to look worn, but staff is very attentive and very nice. Great location, nice pool and entertainment. "
The price is $260
$331 total
includes taxes & fees
Jun 10 - Jun 11
The Morgan Resort Spa Village
BBQ/picnic area
The Villas at Simpson Bay Resort
4.0 star property
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean, felt safe. Food and shopping in close proximity. "
The price is $164
$197 total
includes taxes & fees
Jun 11 - Jun 12
The Villas at Simpson Bay Resort
Exterior
Simpson Bay Resort, Marina & Spa
4.0 star property
8.8 out of 10, Excellent, (1000)
"I will go there again "
The price is $105
$127 total
includes taxes & fees
Jun 27 - Jun 28
Simpson Bay Resort, Marina & Spa
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.

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 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.

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 lively bars and top-notch restaurants.

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

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a spa tub. Other favorite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Nice & Cosy 3BR Villa with private pool / Ocean View and beach access.

How many vacation rentals are there in Simpson Bay?

With 67 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.

Recent reviews of Simpson Bay properties
Expedia verified reviews

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

5/5 Excellent
"We enjoyed every moment of our stay! Beautiful views! Outstanding staff!"
A verified traveler stayed at Hilton Vacation Club Flamingo Beach St. Maarten
Posted 18 hours ago
Hilton Vacation Club Flamingo Beach St. Maarten