Owner Direct Vacation
Rentals in Simpson Bay
The Best Owner Direct Vacation Rentals in Simpson Bay. Explore thousands of vacation home rentals, large cabins, and villas near Simpson Bay
GUESTS
Explore the Best Simpson Bay Vacation Homes
Looking for the perfect place to stay in Simpson Bay? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Simpson Bay character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Simpson Bay
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- Security/Safety
Popular Neighborhoods for Simpson Bay Vacation Rentals
What are the best areas to stay in Simpson Bay
Discover the top neighborhoods in Simpson Bay and choose a place that suits your stay.
Friday Apr 17
Simpson Bay, Sint Maarten
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Simpson Bay vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Simpson Bay
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
How to Reserve Your Simpson Bay Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Simpson Bay Vacation Rental FAQs
There are a lot of options in Simpson Bay. If you plan on staying in the Simpson Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Simpson Bay:
- Anchor House - Direct Oceanfront - Luxury & Modern Style
- 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! nRates start at 250/nt!
- Top of the art penthouse on the beach - 4000 sq. ft of luxury
- LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
- WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
- ALMA - DIRECT BEACH ACCESS 4 BR VILLA
- The Penthouse at LaSiesta nnStunning views in luxurious surroundings!
- Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten
- Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV.
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
There are 115 vacation rentals with private pools near Simpson Bay. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Simpson Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Simpson Bay:
Currently, the total number of properties listed in 2026 is over 698 in the Simpson Bay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Simpson Bay.