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Compare 27 Vacation Homes in Simpson Bay with updated reviews, rates, and availability.

Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay!

10.0 out of 10, Exceptional, (2)
"Super easy process for checking in & out .Also , very friendly helpful staff !"
Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay!

White Sands Retreat - Beachside at Beacon Hill

9.0 out of 10, Wonderful, (33)
"Five minutes walk to the beach. Nice little house."
White Sands Retreat - Beachside at Beacon Hill

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

10.0 out of 10, Exceptional, (3)
"This was an excellent place to bring our family to ! The beautiful house was spacious with multiple bedrooms and a large living area. The outside space was also great with a really nice pool for adults and kids and lots of outdoor seating . There is also access to the beach! We really enjoyed our stay and the view was spectacular !! Eli was always available to answer questions and help to make our stay memorable !"
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

Nice & Cosy 3BR Villa with private pool / Ocean View and beach access

10.0 out of 10, Exceptional, (4)
"The villa looks understated from the outside. Once you walk in the front garden, and into the front door, it's amazing. Beautiful home with beautiful views."
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access

Caribbean Sea Studio next to The Morgan Resort

8.0 out of 10, Very Good, (1)
The price is SAR 487
SAR 750 total
includes taxes & fees
27 Apr - 28 Apr
Caribbean Sea Studio next to The Morgan Resort

Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

The price is SAR 600
SAR 983 total
includes taxes & fees
26 Apr - 27 Apr
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

Coco's Beach House with pool - Simpson Bay Beach

9.4 out of 10, Exceptional, (3)
"Problems galore but most handled quickly. Both bedroom a/c quit because completely rusted through. First a/c guy (Tony) was absolutely useless. He spent 2.5 hours and fixed nothing. Second group of a/c guys (coolite) were outstanding and spent 4.5 hours and returned in morning to clean up trash. Most outlets did not work and had to make coffee in living room. Electrician could not fix as problem was in street so fixed next day. Went a few days without satellite which makes no sense for this kind...
Coco's Beach House with pool - Simpson Bay Beach

Villa Myles: Beachfront

10.0 out of 10, Exceptional, (1)
"This property was perfect for three couples. The principal bedroom with its own ensuite was located on the second level. On the main level there were two other bedrooms, one with an ensuite washroom and the other with the washroom just outside the bedroom. You can walk to Simpson's Bay beach or Maho. The property was clean, and housekeeping came in twice during our weeklong stay. We met the owner of the property, and he was very nice. The property management company was not the best that we have...
Villa Myles: Beachfront

Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite

The price is SAR 600
SAR 979 total
includes taxes & fees
1 May - 2 May
Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite

La Madrague, cosy house with private pool few steps to the beach

9.8 out of 10, Exceptional, (8)
"The place was outstanding. Close to everything yet secluded enough to relax. Property manager was outstanding in helping us out with island, recommendations, and reservations. Really a solid stay."
La Madrague, cosy house with private pool few steps to the beach

Charming 3BR Villa w Private Pool in Pelican Key

The price is SAR 1,370
SAR 2,919 total
includes taxes & fees
26 Apr - 27 Apr
Charming 3BR Villa w Private Pool in Pelican Key

Mary's Beach House

8.0 out of 10, Very Good, (1)
"The contact person is inaccurate in the listing and can not be reached as she is not the correct contact for this property. I messaged 2 times and no response. In addition it states in the description to have a “ fully equipped kitchen” , that was not the case. The was no oven , as stated in listing. That is not a fully equipped kitchen. A kitchen.” Additionally the microwave in the house shocks you when you push the open button"
Mary's Beach House

New listing! Blue View .. stunning views of endless sea!

New listing! Blue View .. stunning views of endless sea!

Pelican Pearl Villa - GENERATOR

Pelican Pearl Villa - GENERATOR

Logan's Run St Maarten

4.0 star property
Logan's Run St Maarten

Casa Picassa - Charming Beachfront 1 bedroom with Private Beach Access

10.0 out of 10, Exceptional, (4)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location. Local vibe but access to plenty. Beautiful view. Private beach!! "
Casa Picassa - Charming Beachfront 1 bedroom with Private Beach Access

Blue Sail Villa. 2 bedroom with pool

7.0 out of 10, Good, (2)
"Nette woning met fijn uitzicht en aardig on site management. Goede prijs/kwaliteit verhouding. Zou aangenamer kunnen zijn als enkele zaken gerepareerd worden, zoals klemmende badkamer deur, douchekraan en schuifdeur van het balkon."
Blue Sail Villa. 2 bedroom with pool

Entire apartment hosted by Alvin

Entire apartment hosted by Alvin

Luxury 2 BED Beachfront Penthouse- SIMPSON BAY

Luxury 2 BED Beachfront Penthouse- SIMPSON BAY

Simpson Bay Penthouse

4.0 star property
Simpson Bay Penthouse
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

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1011)
"Great place to vacation with family "
The price is SAR 542
SAR 668 total
includes taxes & fees
10 May - 11 May
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
9.2 out of 10, Wonderful, (25)
"Great place to stay! "
The Hills Residence

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (27)
"Was an amazing stay definitely recommend this place ! "
Tradewinds at Simpson Bay
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.