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Featured Vacation Rentals in Simpson Bay

Studio Pinel
Studio Pinel
3.5 out of 5.0 22 Rue de Grandes Cayes, Cul de Sac
Studio Pinel offers a private beach, an outdoor pool, and a terrace. If you decide to drive, there's free parking. Other amenities at this beach vacation home ...
Villa Amalia
Villa Amalia
5.0 out of 5.0 Guana Bay Point, Philipsburg
At this vacation home, guests enjoy an outdoor pool, a 24-hour fitness center, and free WiFi in public areas. A stay here includes free valet parking. Other ...
Sea View Lodge Nestled in a Small Tropical Garden With Small Pool
Sea View Lodge Nestled in a Small Tropical Garden With Small Pool
Rue de Grande Caye, #8 Residence Sun Rise View, Cul de Sac, Collectivité de Saint-Martin
At this vacation home, guests have access to a garden. Transportation is made easy with limo/town car service. Helpful staff is there to provide concierge services, ...
House With 2 Bedrooms in Quartier D'orléans, With Wonderful Mountain View, Furnished Balcony and Wifi
House With 2 Bedrooms in Quartier D'orléans, With Wonderful Mountain View, Furnished Balcony and Wifi
Lot Spring 44, Quartier d Orleans
$311
Guests of this vacation home enjoy features like free WiFi in public areas. Free parking is available if you drive.
Villa Flagrantia, Paradise at Your Pleasure
Villa Flagrantia, Paradise at Your Pleasure
Philipsburg, Sint Maarten
At this vacation home, guests have access to a garden.
House in Residence With Swimming Pool
House in Residence With Swimming Pool
Cul de Sac, Collectivity of Saint Martin
At this vacation home, guests have access to a garden.
Beautiful Villa Bottom, sea View
Beautiful Villa Bottom, sea View
Quartier d Orleans, Collectivity of Saint Martin
This vacation home is a smoke-free vacation home.
Carbon Paradise Home
Carbon Paradise Home
Philipsburg, Sint Maarten
Located in Point Blanche, this vacation home is within 1 mi (2 km) of Leeward Islands, Museum of Sint Maarten, and Great Bay Beach. Cyrus Wathey Square and Philipsburg ...
Amazing House With Balcony and Wifi
Amazing House With Balcony and Wifi
Quartier d Orleans
Located in Orient Bay, this vacation home is 0.1 mi (0.1 km) from Leeward Islands and 1.5 mi (2.4 km) from Orient Bay Beach. Coconut Grove Beach and Butterfly ...
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Vacation Rentals

Book vacation rentals in Simpson Bay
Next time you take a group getaway top Simpson Bay, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Simpson Bay; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Simpson Bay rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Simpson Bay is sure to be a winner.

Hotel Options in Simpson Bay

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.