Simpson Bay Holiday Rentals

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Holiday Rentals in Simpson Bay

Orchid | View from room
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 NZ$364
per night
26 May - 27 May
The Horny Toad Guesthouse
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites
3.5 star property
6.8 out of 10, (100)
"Convenient location with the requisite amenities for local stay and business. Water pressure could be improved. Though clean and tidy furniture could be modernized. "
The price is NZ$223
per night
25 May - 26 May
Simpson Bay Suites
Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
10.0 out of 10, Exceptional, (66)
""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
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Exterior
Tradewinds at Simpson Bay
3.5 star property
8.6 out of 10, Excellent, (10)
"The room was spacious and spotless . The staff were attentive and went out of their way to ensure that we were comfortable. Nothing was too much trouble.Will be back excellent stay "
Tradewinds at Simpson Bay
Interior
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
10.0 out of 10, Exceptional, (24)
"Our family of 5 (2-10yr old boys, 1-14yr old girl) were very pleased with the condo. The location was prime in Simpson Bay. Within walking distance to a few beach bars and walked over to Maho Beach too a few times. The pool was nice (warm) and had plenty of seating, always a few seats available. There are beach chairs, toys on the porch along with a beach umbrella. The kitchen was well equipped and left us not needing anything. Bath linens could use a refresh but was sufficient. The only...
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Outdoor pool
Oceanfront amazing 2 bedrooms Condo
9.8 out of 10, Exceptional, (49)
"The condo was very nice. The furnishings were as expected and very tastefully done. The only detractor was the cleanliness of the pool. It needs more attention than what it currently receives and it is full sun. There is no shaded area if you’re hoping to take a break from the sun."
Oceanfront amazing 2 bedrooms Condo
Property grounds
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
9.6 out of 10, Exceptional, (71)
"Beautiful building, property, and very spacious condo with great views. Highly recommended."
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
Property grounds
Anchor House - Direct Oceanfront - Luxury & Modern Style
10.0 out of 10, Exceptional, (125)
"This property is simply stunning. Very clean. Safe area. Walkable to restaurants, bars, markets and the beach, however we did rent a car. Property manager Stacey was amazing. The pictures are spot on for this property and we are booking again in the coming months! I was a little worried that sometimes you aren’t sure what you are booking but this was amazingly perfect. Can’t wait to go back!"
Anchor House - Direct Oceanfront - Luxury & Modern Style
Outdoor pool
BEACHFRONT DESIGN VILLA
9.8 out of 10, Exceptional, (111)
"Stacey was great and set up our excursions which were great. House was perfect!"
BEACHFRONT DESIGN VILLA
Pool
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
10.0 out of 10, Exceptional, (80)
"As advertised. There is a security guard shack steps from the property which is manned 6 pm - 6am."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
On the beach, beach bar
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
9.8 out of 10, Exceptional, (20)
"Nice property. Grounds and pool maintained. Stayed for 2 weeks. We do cook meals at least half the time and found the kitchen could use some necessities like cups and bowls. Also, living room furniture is lacking seating and current furniture is uncomfortable. Other than that it would be nice if each bedroom had a TV. We will return."
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
On the beach, sun-loungers, beach towels
White Sands Retreat - Beachside at Beacon Hill
9.0 out of 10, Wonderful, (25)
"Five minutes walk to the beach. Nice little house."
White Sands Retreat - Beachside at Beacon Hill
Property grounds
Top of the art penthouse on the beach - 4000 sq. ft of luxury
9.8 out of 10, Exceptional, (59)
"Well laid out property, centrally located on the ilsland wirh rhe bonus of being on the Simpson Bay beachfront."
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Outdoor pool
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
Exterior
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 NZ$354
per night
25 May - 26 May
Maho Beach Escape; Sunset Ocean View
On the beach, sun-loungers, beach towels
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay over Easter weekend. The beach was busy."
The price is NZ$503
per night
28 May - 29 May
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio
Fourteen at Mullet Bay
3.5 star property
9.6 out of 10, Exceptional, (116)
"Beautiful and peaceful definitely going back"
Fourteen at Mullet Bay
Sundeck
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 NZ$1,225
per night
31 May - 1 Jun
Dawn Beach Club Resort Sint Maarten
Front of property
July Apartments
3.0 star property
9.2 out of 10, Wonderful, (69)
"That you have to park outside the premises of the resort."
The price is NZ$133
per night
6 Jun - 7 Jun
July Apartments
Sun-loungers, beach towels
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
10.0 out of 10, Exceptional, (8)
"The house was just as listed and the area was perfect. We enjoyed our stay and would recommend and will return!"
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
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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.

Other types of properties in Simpson Bay you may be interested in

Outdoor pool, pool loungers
The Morgan Resort Spa Village
4.0 star property
9.2 out of 10, Wonderful, (1215)
"Great property"
The price is NZ$611
per night
4 Jun - 5 Jun
The Morgan Resort Spa Village
BBQ/picnic area
The Villas at Simpson Bay Resort
4.0 star property
9.2 out of 10, Wonderful, (1005)
"All good "
The price is NZ$322
per night
11 Jun - 12 Jun
The Villas at Simpson Bay Resort
Exterior
Simpson Bay Resort, Marina & Spa
4.0 star property
8.8 out of 10, Excellent, (1000)
"I will go there again "
The price is NZ$200
per night
1 Jun - 2 Jun
Simpson Bay Resort, Marina & Spa
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Simpson Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Simpson Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Simpson Bay. Seeing all the best attractions is bound to make you fall in love with Simpson Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Simpson Bay short-term rentals, that won’t be hard to do.

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 lively bars and top-notch restaurants.

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 67 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. Simpson Bay Beach and Hollywood Casino are other places to visit while you're in town.

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.

Recent reviews of Simpson Bay properties
Expedia verified reviews