Search Vacation Homes in Simpson Bay

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Compare 23 Vacation Homes in Simpson Bay with updated reviews, rates, and availability.

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
Terrace/patio
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
10.0 out of 10, Exceptional, (2)
"Jacob & Eli were gracious and responsive hosts. We had great communication and directions for the property. It was amazing to have a pool and a snorkeling beach at the same property. Outdoor grill worked great. We were able to park 3x small cars in the drive. Neighborhood is quiet and secure. Other reviews mention the airport noise but frankly we rarely heard anything over the sound of the waves on the beach!. No sargassum. Beach can be tricky to enter water but snorkeling is was nice. Kitchen...
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool
White Sands Retreat - Beachside at Beacon Hill
Simpson Bay Beach. Two mile long white sand 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
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access
Pool
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access
10.0 out of 10, Exceptional, (3)
"The pictures are accurate and house was very nice and spotless. House cleaners came every 2 days which was a pleasant surprise. Disappointed that there was no washer/dryer. I understood from the listing that it was available….I just would’ve packed differently. Kids enjoyed the pool and the sunsets are amazing. Stacey the house manager was the best! She stayed late to let us in as our flight was late. We forgot something when we checked out and she helped us get it back! I can’t say enough good...
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access
Caribbean Sea Studio next to The Morgan Resort
Interior
Caribbean Sea Studio next to The Morgan Resort
8.0 out of 10, Very Good, (1)
The price is AED 615
AED 884 total
includes taxes & fees
22 Nov - 23 Nov
Caribbean Sea Studio next to The Morgan Resort
Spacious, Beacon Hill House
Property grounds
Spacious, Beacon Hill House
10.0 out of 10, Exceptional, (1)
"This house is perfect for a foursome. It looks just like the pictures. It was very clean and we never saw a bug. Shelby greeted us upon our arrival. It’s in a great location. We walked to D’s Beach Bar often which is a perfect place to sunbathe and eat and drink."
Spacious, Beacon Hill House
Villa Myles: Beachfront
Pool
Villa Myles: Beachfront
Villa Myles: Beachfront
La Madrague, cosy house with private pool few steps to the beach
Pool
La Madrague, cosy house with private pool few steps to the beach
9.8 out of 10, Exceptional, (8)
"Met by the awesome host Isa. The house is amazing. There is a full kitchen complete with everything you need. Each room has its own patio area, including the king bed that opens to the pool. It’s a small pool, about 4ft deep but tons of fun. The upstairs master has a view of the ocean, magnificent. Not far from the beach, you could walk but we drove. Great air conditioning. Secure neighborhood. We were very glad we rented a car it definitely was needed. Thank you Isa for your warm welcome we...
La Madrague, cosy house with private pool few steps to the beach
Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club
Balcony leading from the living room.
Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club
2.0 star property
Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club
Peaceful Paradise
Living area
Peaceful Paradise
Peaceful Paradise
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite
The price is AED 404
AED 749 total
includes taxes & fees
28 Nov - 29 Nov
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite
La Madrague à Deux pas de la Plage
Outdoor dining
La Madrague à Deux pas de la Plage
La Madrague à Deux pas de la Plage
Entire apartment hosted by Alvin
Room
Entire apartment hosted by Alvin
Entire apartment hosted by Alvin
New listing! Blue View .. stunning views of endless sea!
Living area
New listing! Blue View .. stunning views of endless sea!
New listing! Blue View .. stunning views of endless sea!
Simpson Bay Penthouse
Pool
Simpson Bay Penthouse
4.0 star property
Simpson Bay Penthouse
Blue Sail Villa. 2 bedroom with pool
Pool
Blue Sail Villa. 2 bedroom with pool
7.0 out of 10, Good, (2)
"They may still be fixing things from Irma, but was a little disappointed. The bathroom had no handle on the shower so had to control the water with the small lever that should be inside the handle. The bathroom smelled musty and the shower was missing tile and the door did not close properly.. There were small ants crawling in through a crack by the window and they were everywhere- from the kitchen to the bathroom and the dining table. There were no beach towels provided and the towels they did...
Blue Sail Villa. 2 bedroom with pool
Gated Townhouse in Pelican Key- 1 block from Ocean!
Pool
Gated Townhouse in Pelican Key- 1 block from Ocean!
Gated Townhouse in Pelican Key- 1 block from Ocean!
Logan's Run St Maarten
Room
Logan's Run St Maarten
4.0 star property
Logan's Run St Maarten
Luxury 2 BED Beachfront Penthouse- SIMPSON BAY
Room
Luxury 2 BED Beachfront Penthouse- SIMPSON BAY
Luxury 2 BED Beachfront Penthouse- SIMPSON BAY
Pelican Key Ocean View 3 Bedroom 2 Bathroom Condo
Room
Pelican Key Ocean View 3 Bedroom 2 Bathroom Condo
Pelican Key Ocean View 3 Bedroom 2 Bathroom Condo
Pelican Pearl Villa - GENERATOR
898e8981 1b3e 412c b5ae c824f575b481
Pelican Pearl Villa - GENERATOR
Pelican Pearl Villa - GENERATOR
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 property types in Simpson Bay

The Horny Toad Guesthouse
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 AED 631
AED 817 total
includes taxes & fees
22 Nov - 23 Nov
The Horny Toad Guesthouse
Simpson Bay Suites
Exterior
Simpson Bay Suites
3.5 star property
6.8 out of 10, (104)
"They are very accommodating 👍"
The price is AED 496
AED 555 total
includes taxes & fees
22 Nov - 23 Nov
Simpson Bay Suites
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste with Generator
Pool
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
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.