Simpson Bay Vacation Rentals

Choose from 326 vacation rentals located in Simpson Bay, Sint Maarten. Top filters in Simpson Bay include Air conditioner, Internet / Wifi, and Kitchen or Kitchenette. Prices range from $77 to $4,829 per night. Our most popular vacation rental types near Simpson Bay are Hotel and RV.

Top vacation rentals in Simpson Bay

Beachfront

4.9

Outstanding(112 Reviews)

BEACHFRONT DESIGN VILLA

Villa

in Beacon Hill

10 guests · 4 bedrooms · 5 baths

Garden · Pool · Kitchen or Kitchenette

Indulge in a peaceful retreat at BEACHFRONT DESIGN VILLA, our elegant Villa in Simpson Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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4.9

Outstanding(131 Reviews)

Anchor House - Direct Oceanfront - Luxury & Modern Style

Apartment

in Cupecoy

6 guests · 3 bedrooms · 4 baths

Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Simpson Bay? Look no further than our Apartment, Anchor House - Direct Oceanfront - Luxury & Modern Style. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

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3.5

Average(426 Reviews)

Travel Inn Hotel Simpson Bay

Hotel

in Simpson Bay

3star

1 king bed

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Simpson Bay at Travel Inn Hotel Simpson Bay for $191 for your next trip.

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Beachfront

3.8

Good(464 Reviews)

Atrium Beach Resort and Spa St Maarten

Hotel

in Simpson Bay

4star

1 king bed

Pool · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Simpson Bay? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

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Vacation rentals with air conditioning in Simpson Bay

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5.0

Outstanding(83 Reviews)

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

Villa

in Beacon Hill

6 guests · 3 bedrooms · 3 baths

Garden · Pool · Kitchen or Kitchenette

Nestled in Simpson Bay, this Villa is perfect for your next vacation. Enjoy 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!'s top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

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4.8

Outstanding(89 Reviews)

Oceanfront amazing 2 BR Villa - 2 min from the beach

Villa

in Beacon Hill

4 guests · 2 bedrooms · 2 baths

Garden · Pool · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Simpson Bay at Oceanfront amazing 2 BR Villa - 2 min from the beach for $623 for your next trip.

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3.4

Average(90 Reviews)

Simpson Bay Suites

Apartment hotel

in Simpson Bay

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

The best choice in Simpson Bay for Apartment hotel, for $191 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront

4.0

Good(468 Reviews)

Mary's Boon Beach Plantation Resort & Spa

Hotel

in Simpson Bay

4star

1 king bed

Garden · Pool · Pets allowed

Enjoy the best of Simpson Bay in our Hotel, Mary's Boon Beach Plantation Resort & Spa. A stunning property with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$

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Simpson Bay

Simpson Bay travel guide

Let us help you plan your perfect Simpson Bay vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Simpson Bay, and more.