Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

The Horny Toad Guesthouse
3 out of 5
2 Vlaun Drive, Simpson Bay
The price is $149 per night from May 26 to May 27
Stay at this 3-star beach apartment in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the spacious rooms ...
4.8/5 Exceptional! (38 reviews)
"Loved the views, the privacy and the beach at your front door. But to top it off Debbie & her Husband went out of their way to make sure I was good my whole stay. Definitely recommend & will definitely be back!"

Reviewed on May 16, 2022

The Horny Toad Guesthouse
Simpson Bay Suites
3.5 out of 5
Elmanar Plaza 3D Billy Folly Road, Cole Bay, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is $122 per night from May 26 to May 27
Stay at this 3.5-star business-friendly aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and 3 beach bars. Our guests praise the spacious rooms in our ...
3.3/5 (84 reviews)
"Staff was very accommodating, friendly and helpful."

Reviewed on Apr 11, 2022

Simpson Bay Suites
Cliff House
3.5 out of 5
Beacon Hill Road, Beacon Hill, Simpson Bay, 1744
Stay at this 3.5-star villa in Simpson Bay. Enjoy free WiFi, a furnished balcony, and a TV. Popular attractions Mullet Bay Beach and Dunes Casino are located ...
Cliff House
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Large Ocean Studio on Maho Beach
The price is $155 per night from Jun 17 to Jun 18
Stay at this vacation home in Simpson Bay. Enjoy 1 bedroom. Popular attractions Mullet Bay Beach and Dunes Casino are located nearby. Discover genuine guest ...
5/5 Exceptional! (1 review)
"The property was exactly what they promised. Great location, clear communication, safe and easy to get to. Very satisfied!"

Reviewed on Jan 12, 2022

Large Ocean Studio on Maho Beach
Maho Beach, Airport, Dining, Shopping, - all nearby | Book Now!
The price is $74 per night from Jun 1 to Jun 2
Stay at this family-friendly apartment in Simpson Bay. Enjoy free WiFi, onsite parking, and fenced yards. Popular attractions Mullet Bay Beach and Dunes Casino ...
5/5 Exceptional! (1 review)
Reasonably priced, great location. Clean and relaxing!!!
"Our first trip to St Maarten and definitely not our last. We will definitely stay here again. Our host Daniel was always reachable whenever we needed him. The location cannot be beat. Great room and a very comfy bed made Our stay all the better. If you are looking for a quiet, clean and comfy place ..."

Reviewed on Aug 21, 2021

Maho Beach, Airport, Dining, Shopping, - all nearby | Book Now!
Oceanfront amazing 2 bedrooms Condo
Stay at this family-friendly condo in Simpson Bay. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the WiFi in our reviews. Popular attractions ...
4.7/5 Exceptional! (12 reviews)
3 months in paradise
"The property was exactly as listed. Positives - Amazing location, quiet and comfortable, great view and pool, Ocean right next to us, Muna the housekeeper, Stacey & John the managers were great to deal with. Negatives - The place is starting to show a little tiredness, staying for so long we needed ..."

Reviewed on Apr 24, 2022

Oceanfront amazing 2 bedrooms Condo
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
Stay at this condo in Simpson Bay. Enjoy a beach locale, WiFi, and onsite parking. Our guests praise the restaurant and the WiFi in our reviews. Popular attractions ...
4.7/5 Exceptional! (26 reviews)
Fun
"Great time"

Reviewed on Mar 9, 2022

*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
Close to Maho Beach, Airport, Dining | Book Now!
The price is $66 per night from May 26 to May 27
Stay at this apartment in Simpson Bay. Enjoy free WiFi, onsite parking, and fenced yards. Popular attractions Mullet Bay Beach and Dunes Casino are located nearby. ...
Close to Maho Beach, Airport, Dining | Book Now!
Lovely Ocean Front 1-Bedroom Condo in Maho!
Stay at this vacation home in Simpson Bay. Enjoy 1 bedroom. Popular attractions Mullet Bay Beach and Dunes Casino are located nearby. Discover genuine guest ...
5/5 Exceptional! (1 review)
Great time!
"Great direct view of Ocean and sunsets from lanai, great view of Ocean from bed! Living room, dining room and Kitchen, granite countertops, new Kitchen and bath cabinets, stainless appliances, walking distance to Sunset Beach/ Moho beach where the planes land/fly directly over your head. Sunset Beach ..."

Reviewed on Mar 13, 2020

Lovely Ocean Front 1-Bedroom Condo in Maho!
ON THE BEACH duplex - Fully renovated
Stay at this property in Simpson Bay. Enjoy free WiFi, a beach locale, and onsite parking. Popular attractions Mullet Bay Beach and Dunes Casino are located ...
ON THE BEACH duplex - Fully renovated
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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.

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

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is $306 per night from May 29 to May 30
The Morgan Resort Spa Village
The Villas at Simpson Bay Beach Resort and Marina

The Villas at Simpson Bay Beach Resort and Marina

4 out of 5
Billy Folly Road No. 37A, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is $145 per night from Jun 11 to Jun 12
The Villas at Simpson Bay Beach Resort and Marina
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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Simpson Bay vacation rentals range between $66 per night and $306 per night.

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. 

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