Search Vacation Homes in Simpson Bay

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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!
Pool

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
On the beach, sun loungers, beach towels

White Sands Retreat - Beachside at Beacon Hill

9.0 out of 10, Wonderful, (32)
"The house was the right size for us. Plenty of room for three people. Location on Beacon Hill is fantastic for walking to Maho to see the landings, but also Simpson Bay beach access is no more than 150 feet. Gary provided chairs and umbrellas for the beach, also a small cooler. We were temporary locals and close to D's, which is a good beach bar.The whole thing was perfect for our needs, including off-street parking."
White Sands Retreat - Beachside at Beacon Hill
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, (3)
"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
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access
Outdoor pool

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

10.0 out of 10, Exceptional, (4)
"My family of 4 enjoyed this property! The home was very comfortable and well appointed with everything we needed for a perfect vacation. The home was immaculate and beautifully decorated. We were truly in awe of the ocean views from the main living area and pool deck. Perfect spot to watch the sunset with a cocktail and I enjoyed my morning coffee up on the balcony of the main suite overlooking the ocean. We thought the location was great. Easy to walk to bars, restaurants and shops. We...
Nice & Cosy 3BR Villa with private pool / Ocean View and beach access
Caribbean Sea Studio next to The Morgan Resort
Property grounds

Caribbean Sea Studio next to The Morgan Resort

8.0 out of 10, Very Good, (1)
The price is SAR 597
SAR 874 total
includes taxes & fees
11 Apr - 12 Apr
Caribbean Sea Studio next to The Morgan Resort
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite
Beach nearby

Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

The price is SAR 750
SAR 1,144 total
includes taxes & fees
6 Apr - 7 Apr
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite
Coco's Beach House with pool - Simpson Bay Beach
On the beach

Coco's Beach House with pool - Simpson Bay Beach

9.4 out of 10, Exceptional, (3)
"Lia is a terrific host. Great communication leading up to the trip and during our stay. She arranged for a car rental to meet us at the airport. Super easy. Our stay at Coco Beach was terrific. Highly recommend. Great location to beaches and restaurants."
Coco's Beach House with pool - Simpson Bay Beach
Villa Myles: Beachfront
Outdoor pool

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
Beach nearby

Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite

The price is SAR 750
SAR 1,133 total
includes taxes & fees
9 Apr - 10 Apr
Turquoise Room · CocoVaa Boutique Hotel - Turquoise Suite
La Madrague, cosy house with private pool few steps to the beach
Beach nearby, sun loungers, beach towels

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
Charming 3BR Villa w Private Pool in Pelican Key
Pool

Charming 3BR Villa w Private Pool in Pelican Key

The price is SAR 1,392
SAR 2,598 total
includes taxes & fees
7 Apr - 8 Apr
Charming 3BR Villa w Private Pool in Pelican Key
Mary's Beach House
Outdoor pool

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!
Smart TV, books

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

New listing! Blue View .. stunning views of endless sea!
Pelican Pearl Villa - GENERATOR
Outdoor dining

Pelican Pearl Villa - GENERATOR

Pelican Pearl Villa - GENERATOR
Logan's Run St Maarten
Exclusive House, 2 Bedrooms, Non Smoking, Sea View | Private kitchen | Oven, stovetop, dishwasher, cookware/dishes/utensils

Logan's Run St Maarten

4.0 star property
Logan's Run St Maarten
Blue Sail Villa. 2 bedroom with pool
Outdoor 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
Casa Picassa - Charming Beachfront 1 bedroom with Private Beach Access
On the beach

Casa Picassa - Charming Beachfront 1 bedroom with Private Beach Access

10.0 out of 10, Exceptional, (4)
"So nice to wake up and walk right out on the beach every morning. Host was exceptionally great!! very communicative and helped me find my way around. Next time I’m down I will want to stay here, 100%"
Casa Picassa - Charming Beachfront 1 bedroom with Private Beach Access
Simpson Bay Penthouse
Outdoor pool

Simpson Bay Penthouse

4.0 star property
Simpson Bay Penthouse
Entire apartment hosted by Alvin
Fridge, microwave, oven, stovetop

Entire apartment hosted by Alvin

Entire apartment hosted by Alvin
Luxury 2 BED Beachfront Penthouse- SIMPSON BAY
Pool

Luxury 2 BED Beachfront Penthouse- SIMPSON BAY

Luxury 2 BED Beachfront Penthouse- 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.
Don't see what you're looking for?
See all available properties in Simpson Bay
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten
Outdoor pool, sun loungers

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1003)
"We really enjoyed our stay at the Royal Palm. Top notch."
The price is SAR 674
SAR 806 total
includes taxes & fees
3 May - 4 May
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Amazing Top Floor Apartment | Balcony

The Hills Residence

3.0 star property
9.4 out of 10, Exceptional, (21)
"I loved staying at The Hills because it was very centric, easy to move around. The property has an amazing view with a pool, beautiful decor comfortable bed. I love it all. I will recommend it. I am staying here again. "
The Hills Residence
Simpson Bay Suites
Beach nearby, white sand, sun loungers, beach umbrellas

Simpson Bay Suites

3.5 star property
6.8 out of 10, (120)
"Highly recommended and friendly staff…"
The price is SAR 506
SAR 567 total
includes taxes & fees
16 Apr - 17 Apr
Simpson Bay Suites
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.