Simpson Bay condos
We found 1,080 condos — enter your dates for availability
Explore Simpson Bay condo rentals
Oceanfront amazing 2 bedrooms Condo
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
Sleeps 6 · 2 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Anchor House - Direct Oceanfront - Luxury & Modern Style
Sleeps 6 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
Ocean's Edge 2B directly on Simpson Bay Beach
Sleeps 3 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
Top rated condo and apartment rentals - Simpson Bay
Winter escape
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Our stay was great. The unit is an ideal location, well stocked, and beach and pool are lovely.Our hosts were quick to respond if we had a question.
Brad E.
Stayed Mar 2025
Perfect Accommodation
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
We had an amazing week at Kim's condo. Stunning harbour views. All three pools were gorgeous and never busy. Excellent location. Can't wait to return. Kim was very responsive.
Jenny K.
Stayed Jan 2025
Simpson Bay Yacht Club
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Great Location, walking distance to many restaurants, beaches. Condo is well equipped with many amenities. Pool is located right outside your back door with a few steps up to the pool deck. Steve the host is amazing, answered all our questions promptly. Messaged us a few days into our stay to make sure everything was going well.
Ronald M.
Stayed Jan 2025
Great beach location
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Perfect location in Simpson Bay, 2 steps from the beach. Lovely upper patio to watch sunsets. Owners very friendly and helpful!
Renee G.
Stayed Dec 2024
Excellent Service
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
I’d you’re looking for a clean, well kept property walking distance to just about everything in Simpson Bay and great service. This is your spot.
bethany s.
Stayed Dec 2024
Simpson Bay Beauty
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
The place was as advertised- just beautiful, so well equipped. The views are amazing and to be able to watch the planes taxi down the runaway was fantastic. We loved every moment of our stay. Host was so courteous and prompt to respond. Highly recommend staying here.
Ruthie M.
Stayed Mar 2023
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Frequently asked questions
Are there any apartment vacation rentals in Simpson Bay?
Choose from 1,080 apartment vacation rentals in Simpson Bay that have more value, privacy, amenities and space than a standard hotel room. Look into apartments and condos in sought-after neighborhoods such as Pelican Key, Cay Bay and Almond Grove.
How much does it cost to stay in an apartment vacation rental in Simpson Bay?
Apartment vacation rentals close to busy areas in Simpson Bay are usually more expensive. If you want to save, search for stays a little further away but with good transportation links. With Vrbo, you can easily browse your options and find the perfect vacation condo rental at a competitive price.
When is the best time to rent a vacation condo in Simpson Bay?
The most popular month to visit Simpson Bay is March, so if you'd love to experience this destination in its liveliest state, plan your stay then. Average temperatures at this time range from 25ºC (77ºF) to 26ºC (79ºF). Once you've worked out the best time to visit this part of Saint Martin, Vrbo will help you find an apartment vacation rental that offers a homey feel that most hotel rooms can't match.
Where can I rent a Simpson Bay vacation apartment with great views?
Vrbo has some awesome vacation condo rentals in Simpson Bay, including properties with beach views. When you aren't out sightseeing, kick back and gaze at vistas that are an attraction in themselves.
Does Simpson Bay have any weekend apartment rentals?
Switch on your out-of-office message and get away to Simpson Bay for a weekend adventure in a Vrbo apartment vacation rental. A top tip? Be flexible with your preferred dates and book early to have the first choice of some awesome vacation condo rentals.
Can I book a luxury apartment in Simpson Bay?
Book one of our luxury apartment vacation rentals in popular destinations like Pelican Key and get ready to live the good life during your Simpson Bay retreat. You can forget about roughing it at these vacation condo rentals. Offering top-quality perks like indoor or outdoor pools, cozy fireplaces and hot tubs, all you have to do is unpack, stretch out and enjoy.
What are the top things to do in Simpson Bay?
Maho Beach, Mullet Bay Beach and Simpson Bay Beach are top attractions that'll keep the whole family occupied in Simpson Bay. There's nothing like travel to bring everyone together, so browse our apartment vacation rentals in this exciting destination.
Why should I book my apartment vacation rental with Vrbo?
Book your apartment vacation rental with Vrbo and get more privacy and space compared to standard hotel accommodations. These kinds of stays promise that home-away-from-home ambience. One of the biggest pluses? You'll never have to share your space, whether you spend your trip in an apartment or somewhere a little swankier, like a villa or an estate.