592+ Vacation Rentals & Holiday Homes in Simpson Bay |
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Simpson Bay Accommodations - Hotels & Rentals

About Simpson Bay Vacation Rentals

Discover More than 592 Incredible Getaway Rentals Available in Simpson Bay. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Simpson Bay.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Simpson Bay, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Simpson Bay. The Average Size of Places to Stay Near Simpson Bay is 842.4 ft², with Prices Averaging US $507 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Simpson Bay. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Simpson Bay

Type Count
Holiday Apartments 210
Villas 114
Vacation Homes 48
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Simpson Bay

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Simpson Bay with Online Reservations.

Weather in Simpson Bay, SX

View the weather forecast for Simpson Bay before booking your Simpson Bay Vacation Rentals to confirm your best time to go.

December - February
High 85°F       Low 69°F
March - May
High 87°F       Low 72°F
June - August
High 89°F       Low 76°F
September - November
High 88°F       Low 73°F

Activities Simpson BayGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Simpson BayGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Kim Sha Beach
Simpson Bay Beach
Flamingo Beach
Dunes Casino
Hollywood Casino
Lay Bay Beach
Maho Beach
Mullet Bay Beach
American University of the Caribbean
Great Bay Beach
Guana Bay Beach
Cupecoy Beach
Dawn Beach
University of St. Martin
Fort Amsterdam
Starz City Casino
Philipsburg Courthouse
Mullet Bay
Little Bay Beach

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Flamingo Beach 1,514 Properties
Kim Sha Beach 1,511 Properties
Simpson Bay Beach 1,504 Properties
Hollywood Casino 1,460 Properties
Lay Bay Beach 1,438 Properties
Dunes Casino 1,401 Properties
Pelican Key 111 Properties
Beacon Hill 77 Properties

Frequently Asked Questions About Simpson Bay?

What are the top hotels, lake houses & vacation rentals in Simpson Bay?

We provide an array of great vacation destinations in Simpson Bay. If you are looking to stay in or around the Simpson Bay area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Simpson Bay:

How many Hotels & Vacation Rentals have private pools in Simpson Bay?

We have 101 Hotels & Vacation Rentals featuring a private pool in and near Simpson Bay. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Simpson Bay is best for families?

Searching for a family-friendly getaway in Simpson Bay? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Simpson Bay?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 592 in the Simpson Bay area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Simpson Bay.

Nearby Neighborhood (2) 
Neighborhood Property Count
Maho Vacation Rentals in Simpson Bay 458
Pelican Key Vacation Rentals in Simpson Bay 111

People Also Ask

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Recently Booked Hotels, Resorts, or Rentals in Simpson Bay