Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

The Horny Toad Guesthouse
Orchid | View from room
The Horny Toad Guesthouse
3.0 star property
9.4 out of 10, Exceptional, 51 reviews
"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
Jun 22 - Jun 23
The Horny Toad Guesthouse
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
10.0 out of 10, Exceptional, 66 reviews
""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
Simpson Bay Suites
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites
3.5 star property
6.8 out of 10, 101 reviews
"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
Jun 21 - Jun 22
Simpson Bay Suites
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Tradewinds at Simpson Bay
Exterior
Tradewinds at Simpson Bay
3.5 star property
8.6 out of 10, Excellent, 10 reviews
"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
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
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 reviews
"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.
Oceanfront amazing 2 bedrooms Condo
Outdoor pool
Oceanfront amazing 2 bedrooms Condo
9.8 out of 10, Exceptional, 50 reviews
"Spacious condo style unit with secure parking spot (huge benefit). Rooftop pool where you can see the planes taking off was a highlight for our son. TIP: Double check with property manager address prior to arriving. What was sent on our VRBO confirmation was a little confusing based on the address labeling."
Oceanfront amazing 2 bedrooms Condo
Anchor House - Direct Oceanfront - Luxury & Modern Style
Property grounds
Anchor House - Direct Oceanfront - Luxury & Modern Style
10.0 out of 10, Exceptional, 127 reviews
"My friends and I found the home spacious well equipped and breathtaking views .we enjoyed having the and found all the beds to be comfortable. The host and Stacey were attentive . It was exactly as described."
Anchor House - Direct Oceanfront - Luxury & Modern Style
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
Property grounds
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
9.6 out of 10, Exceptional, 72 reviews
"We loved the property! At first we weren't sure about the location but it was so convenient and lots of good restaurants nearby just more residential. It's a quiet beach which was nice as well. The housekeeper went above and beyond to make sure everything was perfect."
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
BEACHFRONT DESIGN VILLA
Outdoor pool
BEACHFRONT DESIGN VILLA
9.8 out of 10, Exceptional, 112 reviews
"An excellent property"
BEACHFRONT DESIGN VILLA
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
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 reviews
"We really enjoyed our stay over Easter weekend. The beach was busy."
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Pool
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
10.0 out of 10, Exceptional, 82 reviews
"Bob was the best host. Communication was so easy before our trip and during our stay. Bob was out of town but made sure all our needs were met. Chevor checked us in and helped us find a tech store to buy a SIM card for our phone to use while on the island. The house is in the perfect location close to everything. The neighborhood felt very safe. The house and pool were exceptionally clean. Bob has the house stocked with everything you need. We loved drinking coffee sitting on the porch or on the...
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Property grounds
Top of the art penthouse on the beach - 4000 sq. ft of luxury
10.0 out of 10, Exceptional, 61 reviews
"Nicely decorated, great space allowing privacy for three couples. Penthouse with hot tub is truly a bonus. The property manager was very responsive as well. Definitely would stay here again!"
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Oceanfront amazing 2 BR Villa - 2 min from the beach
Outdoor pool
Oceanfront amazing 2 BR Villa - 2 min from the beach
9.6 out of 10, Exceptional, 91 reviews
"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
Maho Beach Escape; Sunset Ocean View
Exterior
Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, 3 reviews
"Self check in and out was a nice experience "
The price is $135
$205 total
includes taxes & fees
Jun 22 - Jun 23
Maho Beach Escape; Sunset Ocean View
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
On the beach, beach bar
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
9.8 out of 10, Exceptional, 20 reviews
"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!
White Sands Retreat - Beachside at Beacon Hill
On the beach, sun loungers, beach towels
White Sands Retreat - Beachside at Beacon Hill
9.0 out of 10, Wonderful, 25 reviews
"Five minutes walk to the beach. Nice little house."
White Sands Retreat - Beachside at Beacon Hill
Fourteen at Mullet Bay
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio
Fourteen at Mullet Bay
3.5 star property
9.6 out of 10, Exceptional, 129 reviews
"This was a great place to stay the staff was great & the food around the area was great ! I’ll definitely be back "
Fourteen at Mullet Bay
Dawn Beach Club Resort Sint Maarten
Sundeck
Dawn Beach Club Resort Sint Maarten
4.0 star property
8.6 out of 10, Excellent, 14 reviews
"Nice property, but far away from the airport and party area"
The price is $699
$839 total
includes taxes & fees
Jun 22 - Jun 23
Dawn Beach Club Resort Sint Maarten
July Apartments
Front of property
July Apartments
3.0 star property
9.2 out of 10, Wonderful, 74 reviews
"Probably one of the easiest parking on the island! Front desk staff is always present and very helpful and friendly. Easy to get to and a nice, clean stay."
The price is $68
$81 total
includes taxes & fees
Jul 4 - Jul 5
July Apartments
Mullet Bay Suites: Your Luxury Stay Awaits
Terrace/patio
Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
10.0 out of 10, Exceptional, 49 reviews
"I highly recommend Mullet Bay Suites for its cleanliness, modern amenities, and comfort. The suites offer stunning views, especially in the morning, and feature convenient parking and robust security. The property is just a short walk to the beach, adding to its appeal. The management is excellent, and we received a warm welcome from the property manager, Emmanuel, who greeted us with cold towels and local banana rum—a delightful touch! Emmanuel is attentive, kind, and responsive, providing...
Mullet Bay Suites: Your Luxury Stay Awaits
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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

The Morgan Resort Spa Village
Outdoor pool, sun loungers
The Morgan Resort Spa Village
4.0 star property
9.2 out of 10, Wonderful, 1,292 reviews
"Absolutely enjoyed the stay and the service was awesome!!!"
The price is $252
$324 total
includes taxes & fees
Jul 2 - Jul 3
The Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa
Exterior
Simpson Bay Resort, Marina & Spa
4.0 star property
8.8 out of 10, Excellent, 1,005 reviews
"Great "
The price is $121
$146 total
includes taxes & fees
Jun 24 - Jun 25
Simpson Bay Resort, Marina & Spa
The Villas at Simpson Bay Resort
BBQ/picnic area
The Villas at Simpson Bay Resort
4.0 star property
9.2 out of 10, Wonderful, 1,007 reviews
"Great hotel, located in a great area. The pool area and bar were nice, however, the pool does not have a shallow area to hangout. The rooms were updated and clean, only thing that was missing was a long mirror but otherwise it’s a great hotel for a great price !"
The price is $171
$205 total
includes taxes & fees
Jun 21 - Jun 22
The Villas at Simpson Bay Resort
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 $68 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

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

5/5 Excellent
"Favorite place to stay on the island"
A verified traveler stayed at Simpson Bay Resort, Marina & Spa
Posted 2 days ago
Simpson Bay Resort, Marina & Spa