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Simpson Bay Vacation Rentals(36)

36 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(16)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 10 night minimum stay
(13)
  • 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
(18)
$500 - $643
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 7 night minimum stay
$329
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
(9)
$350 - $750
per night
5 - 10 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
5 - 10 night minimum stay
(16)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
(4)
$215 - $450
per night
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 3
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 6 night minimum stay
(6)
$525 - $929
per night
5 - 10 night minimum stay
  • 2 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 10 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(21)
  • 4 BR,
  • 5 BA,
  • Sleeps 12
(33)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(7)
  • 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)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
1 Review
$150 - $300
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(3)
$215 - $371
per night
4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 night minimum stay
(6)
14 more choices from the HomeAway Network
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$175 - $250
per night
1 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 4 night minimum stay
(5)
$357 - $500
per night
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
$1,100 - $2,000
per week
7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
$1,800 - $2,200
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(7)
$1,750 - $3,300
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(9)
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
7 night minimum stay
1 Review
  • 4 BR,
  • 5 BA,
  • Sleeps 12
1 Review
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Recent Simpson Bay Reviews

Absolutely stunning

5 of 5
This condo was amazing, better than the pictures. Very clean, spacious and new. The deck on the main floor is a great place to relax and have a morning cup of coffee and just look over the beautiful sea. The penthouse deck has a 360 degree view which is just as picturesque at night as it is during the day. Sitting in the hot tub with a glass of wine and watching the sunset is something we will always think about. The beach on Simpson Bay is one of the best on the island and you just walk out of the unit and you are there. If you are looking for a high end condo on the beach, I don't believe you will find anything better. Simona was great, very helpful and friendly. This property was beyond our expectations.
  • Submitted: Dec 10, 2014
  • Stayed: Nov 2014

Intimate experience even with child in tow !

5 of 5
What a luxurious treat! This resort is small, personal and intimate, so much better than the mega hotels on so many of the other beaches. And, the beach! almost private and so very beautiful. Loved having the 2 pools to choose from, the bar and restaurant right on site! The staff were friendly, helpful and courteous; everything was so clean and fresh! I thought having the 3 of us (with our 11 yr old sleeping on the pull out chair) would be cramped, but we had plenty of space and what a nice amenity / money saver to have the kitchenette! And, the deck ... coffee and the newspaper with those views. Just lovely. Can't say enough. As far as local activities and restaurants, I'd recommend the Butterfly Farm, the snorkeling adventures with Rock'nRoll Safari, and dinner at Izi ... such fun!
  • Submitted: Nov 7, 2014
  • Stayed: Mar 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