85 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Hotels
Homes
Studios
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Cottages
Estates
Farmhouses
Lodges
Townhomes
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

85 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Simpson Bay Vacation Rentals with pool(85)

85 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(17)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 7 night min stay
(35)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 10 night min stay
(17)
$400 - $786
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 7 night min stay
(8)
$400 - $714
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
5 - 7 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night min stay
(20)
  • 6 BR,
  • 5 BA,
  • Sleeps 12
7 night min stay
(5)
$229 - $329
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 7 night min stay
(4)
$229 - $329
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 7 night min stay
(11)
$229 - $329
per night
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 - 7 night min stay
(13)
$458 - $886
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 night min stay
(3)
$350 - $750
per night
3 - 10 night min stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
3 - 10 night min stay
2 Reviews
  • 1 BR,
  • 2 BA,
  • Sleeps 2
5 night min stay
(9)
$650 - $1,500
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 9
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night min stay
2 Reviews
  • 5 BR,
  • 5 BA,
  • Sleeps 10
(7)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
(6)
$1,643 - $4,286
per night
5 - 14 night min stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 12
5 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 4
(5)
$500 - $2,100
per night
5 - 7 night min stay
  • 5 BR,
  • 5 BA,
  • Sleeps 12
5 - 7 night min stay
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(20)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(23)
$175 - $250
per night
1 - 2 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 2 night min stay
(6)
  • Studio,
  • 1 BA,
  • Sleeps 2
7 night min stay
(8)
  • 2 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 10 night min stay
(4)
$150
per night
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night min stay
(26)
$1,225 - $2,100
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(8)
$239 - $339
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 7 night min stay
1 Review
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night min stay
$151 - $397
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
 

Recent Simpson Bay Reviews

Amazing place!

5 of 5
One of the best location in St Maarten, fron beach awesome mansion very quiet and relaxing and, at the same time, right in the center of Simpson Bay and Pellican that is the place you want to stay during your holiday in the friendly island. Very spacious rooms and beuatiful pool with ocean view.
  • Submitted: May 15, 2015
  • Stayed: Nov 2014

Paradise

5 of 5
The drive to this property concerned me: close to the airport and a neighborhood I wasn't familiar with. BUT when I arrived and the storm shutters opened, I fell in love! This condo is in the perfect location and very safe and secure. All of the rooms are large and so comfortable! I can't wait to come back again!
  • Submitted: Mar 24, 2015
  • Stayed: Mar 2015

TOTAL DESCONNECT BEST LOCATION

5 of 5
FIVE STAR CONDO, BEAUTIFULf!!!!!!! CLEAN!!!!!! STAYED FOR 5 NITES RECOMMEND A CAR IF STAYING FOR MORE NITES, CABS GET EXPENSIVE. HAD DINNER AT BEACH, JUST SIMPLE DESCONNECT FROM THE WORLD. WILL COME AGAIN , WE WERE DEEEPLYYYYY SAD TO LEAVE WISH I HAD MORE STARS!!!!!!! TO GIVE THEO AND HIS PLACE
  • Submitted: Feb 23, 2015
  • Stayed: Feb 2015