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Simpson Bay Beach Vacation Rentals Vacation Rentals(56)

56 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(15)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 7 night minimum stay
(31)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(17)
$175 - $250
per night
1 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 4 night minimum stay
(5)
$350 - $750
per night
5 - 10 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
5 - 10 night minimum stay
(16)
$2,800 - $5,500
per week
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 14 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
2 Reviews
$229 - $329
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
(8)
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 7 night minimum stay
$169 - $299
per night
4 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
4 - 7 night minimum stay
(15)
$300 - $400
per night
5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
5 night minimum stay
(6)
$3,200 - $6,200
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
$314 - $843
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
4 - 7 night minimum stay
2 Reviews
$215 - $315
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 - 7 night minimum stay
(10)
  • 2 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 4
1 Review
$215 - $400
per night
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 3
5 - 7 night minimum stay
$1,400 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(21)
$500 - $645
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 7 night minimum stay
$525 - $929
per night
5 - 10 night minimum stay
  • 2 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 10 night minimum stay
(3)
  • 4 BR,
  • 5 BA,
  • Sleeps 12
(33)
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
$1,225 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(7)
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Recent Simpson Bay Reviews

Island Paradise

5 of 5
We rode out Hurricane Gonzalo on 10/13/14 in the fantastic 3 bedroom penthouse unit. Both Simona and the owner were extremely attentive to our concerns/needs throughout the storm as well as the entire week afterward. The unit was nicely appointed and spacious. The outer patios were magnificant and the sunsets from the rooftop hot tub were breathtaking. The beach in front of the house was practically private (except on weekends). There was plenty of shade from an umbrella and palm trees. The water was crystal clear and warm! Finally, the owners of the adjoining units were very helpful and friendly. Highly recommend!!!
  • Submitted: Oct 23, 2014
  • Stayed: Oct 2014

Beautiful Villa! More than we expected

5 of 5
My girlfriends and I (8 of us) decided on Rick's Seaside Retreat for our girls vacation. This place did not disappoint, the Jacuzzi tubs were just what we needed after a day of sightseeing. The rooms were spacious and beautiful, the kitchen had everything we needed to make a meal. The only thing negative I could say was the gas took longer than what I'm used to with electric. The villa's view I feel is second to none, and I can't think of a better place to have spent my birthday. Jenny was a jewel and we were thankful for her insights and suggestions. Rick, you and Marie have a beautiful home and I thank you for allowing us to experience a bit of paradise.
  • Submitted: Sep 7, 2014
  • Stayed: Aug 2014

Second visit twice as nice!

5 of 5
My wife and I returned to spend another anniversary on the island. Just like the first time, it was perfect! The unit, the property, staff, weather and island....perfect! I would just like to thank Scott, again for sharing what he has. I'd also like to thank Mary for making everything go smoothly. We'll be back again...maybe not next year...but we'll be back.
  • Submitted: Aug 4, 2014
  • Stayed: Jul 2014