Simpson Bay Holiday Rentals

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Holiday Rentals in Simpson Bay

The Horny Toad Guesthouse
3.0 star property
9.4 out of 10, Exceptional, (51)
"Deb & Doug are accommodating and great to talk to to get ideas of things to do. Perfect place to stay!"
The price is AU$341
includes taxes & fees
23 Nov - 24 Nov
The Horny Toad Guesthouse
Simpson Bay Suites
3.5 star property
6.8 out of 10, (104)
"They are very accommodating 👍"
The price is AU$232
includes taxes & fees
23 Nov - 24 Nov
Simpson Bay Suites
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste with Generator
9.8 out of 10, Exceptional, (67)
""We had an incredible stay at Villa Namaste! The property is gorgeous, with every room beautifully appointed. The view from the patio is breathtaking—worth every penny. Sitting in the infinity edge pool, looking out over the bluest Caribbean waters while watching mega yachts sail by, was a highlight of our days. The villa is also conveniently located close to many cool restaurants, some even within walking distance, which was perfect for our evenings out. The staff, particularly Olive and...
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste with Generator
Tradewinds at Simpson Bay
3.5 star property
8.8 out of 10, Excellent, (11)
"It’s beautiful and all the restaurants are across the way! "
Tradewinds at Simpson Bay
Oceanfront amazing 2 bedrooms Condo
9.8 out of 10, Exceptional, (50)
"Spacious condo style unit with secure parking spot (huge benefit). Rooftop pool where you can see the planes taking off was a highlight for our son. TIP: Double check with property manager address prior to arriving. What was sent on our VRBO confirmation was a little confusing based on the address labeling."
Oceanfront amazing 2 bedrooms Condo
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
10.0 out of 10, Exceptional, (26)
"It was located in a pretty beach, on the beginning we were scared of the neiborhood but is not bad because you have restaurants walking distance, the apartment has everything and is really clean and confortable. Also Andrea always responds very quickly. We’ll be back there definitely "
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
BEACHFRONT DESIGN VILLA
9.8 out of 10, Exceptional, (112)
"An excellent property"
BEACHFRONT DESIGN VILLA
Top of the art penthouse on the beach - 4000 sq. ft of luxury
10.0 out of 10, Exceptional, (65)
"Absolute amazing place, with fantastic views, great location and walk out access to the beach and other activities. Can’t wait to get back. "
Top of the art penthouse on the beach - 4000 sq. ft of luxury
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
9.6 out of 10, Exceptional, (75)
"great location, rented car and was able to see alot on the island. comfy bed, quiet and peaceful, excitement just a few blocks away. This was our 3rd visit to Aqualina."
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
10.0 out of 10, Exceptional, (85)
"Beautiful "
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Oceanfront amazing 2 BR Villa - 2 min from the beach
9.6 out of 10, Exceptional, (91)
"We had a wonderful week in St Maarten at the Cliffside property overlooking Simpson Bay. Perfect for 2 couples with great outdoor spaces and views of the water on 2 sides. We will definitely be back!"
Oceanfront amazing 2 BR Villa - 2 min from the beach
White Sands Retreat - Beachside at Beacon Hill
9.0 out of 10, Wonderful, (26)
"We would stay here again if we were to return. We loved the location, enjoyed watching the planes landing and taking off from the front porch, not a noise problem. The property had everything one needed for our stay, washing machine was a bonus as was having everything one needed for the beach. Communication with the owner was great. Walking distance to the Maho Beach area was great, close to bars, restaurants and shopping. We have not a bad word to say about this stay. I hope he will also give...
White Sands Retreat - Beachside at Beacon Hill
Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, (3)
"Self check in and out was a nice experience "
The price is AU$329
includes taxes & fees
26 Nov - 27 Nov
Maho Beach Escape; Sunset Ocean View
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
10.0 out of 10, Exceptional, (7)
"Serenity in the Sand was perfect for our week stay in St. Maarten! Condo was very clean and exactly as pictured. It was well stocked with everything we needed. The view is simply amazing! We started every day with time on the porch watching the gorgeous blue water, all the sailboats. We also enjoyed watching the sunsets from the porch or the beach. We loved the private access to the beach and the provided loungers. Restaurants and stores are close by and we walked to several. We rented a car to...
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
10.0 out of 10, Exceptional, (21)
"The rental was located on the beach with three spacious master suites. Chairs were available as well. Just make sure you know the villa number and how to get the key. I didn’t know that ahead of time. They even let me stay later than expected due to a delayed flight. I’d definitely return."
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
Fourteen at Mullet Bay
3.5 star property
9.6 out of 10, Exceptional, (175)
"The property is well kept, staff are nice"
Fourteen at Mullet Bay
Dawn Beach Club Resort Sint Maarten
4.0 star property
8.6 out of 10, Excellent, (14)
"Nice property, but far away from the airport and party area"
The price is AU$1,288
includes taxes & fees
30 Nov - 1 Dec
Dawn Beach Club Resort Sint Maarten
Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
10.0 out of 10, Exceptional, (65)
"Great property management "
The price is AU$474
includes taxes & fees
30 Nov - 1 Dec
Mullet Bay Suites: Your Luxury Stay Awaits
July Apartments
3.0 star property
9.0 out of 10, Wonderful, (83)
"Front desk staff was very knowledgeable and helpful. "
The price is AU$191
includes taxes & fees
14 Dec - 15 Dec
July Apartments
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
10.0 out of 10, Exceptional, (13)
"Great place!"
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Simpson Bay you may be interested in

The Morgan Resort Spa Village
4.0 star property
9.0 out of 10, Wonderful, (1438)
"Staff was all nice . Had a late check in due to rooms not being ready and was accommodated with drinks . The AC went out for a few hours on my last day and once again was accommodated with a $25 food credit for each party. Food was great & fresh. Hotel was very clean. Pool area also very clean. Taxis are available and all friendly. I would definitely be back. "
The price is AU$526
includes taxes & fees
24 Nov - 25 Nov
The Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa
4.0 star property
8.8 out of 10, Excellent, (1004)
"well planned footprint"
The price is AU$239
includes taxes & fees
25 Nov - 26 Nov
Simpson Bay Resort, Marina & Spa
The Villas at Simpson Bay Resort
4.0 star property
9.2 out of 10, Wonderful, (1105)
"Great beach - not crowded, clear water and lots of chairs. Good location to walk to town. "
The price is AU$301
includes taxes & fees
24 Nov - 25 Nov
The Villas at Simpson Bay Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars.

What are some of the best holiday rentals that Simpson Bay has to offer?

White Sands Retreat - Beachside at Beacon Hill: This highly rated holiday home rental in Simpson Bay is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub. Other favourite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Nice & Cosy 3BR Villa with private pool / Ocean View and beach access.

How many holiday rentals are there in Simpson Bay?

With 61 Expedia holiday rentals, you're guaranteed to find just the right place for your Simpson Bay stay.

What’s there to see and do in Simpson Bay?

Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find popular places such as Maho Beach and Orient Bay Beach.

What’s a holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.