31 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Simpson Bay Vacation Rentals(31)

31 Results
$300 - $400
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
5 - 7 night minimum stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night minimum stay
(3)
$169 - $249
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 7 night minimum stay
(16)
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 7 night minimum stay
1 Review
$229 - $329
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 7 night minimum stay
1 Review
$458 - $886
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 night minimum stay
2 Reviews
$229 - $329
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 - 7 night minimum stay
(12)
$1,643 - $4,286
per night
5 - 14 night minimum stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 12
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 4
1 Review
$239 - $339
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(12)
$3,200 - $4,500
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 night minimum stay
$795 - $1,571
per night
5 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
5 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
5 night minimum stay
(4)
$686 - $1,357
per night
7 - 13 night minimum stay
  • 5 BR,
  • 6 BA,
  • Sleeps 10
7 - 13 night minimum stay
$157 - $229
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
(21)
  • 6 BR,
  • 6 BA,
  • Sleeps 12
7 - 14 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
$310 - $420
per night
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 more choices from the HomeAway Network
$229 - $329
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 7 night minimum stay
(5)
$215 - $300
per night
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
5 - 7 night minimum stay
(3)
$3,150 - $4,550
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 7
7 night minimum stay
$383 - $557
per night
3 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 14 night minimum stay
$229
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
(8)
$1,495 - $1,995
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
Advertisement
 

Recent Simpson Bay Reviews

Great place!

5 of 5
We just got back from this lovely condo. There was 4 of us in our party. The condo is in a gated area. Which we were surprised and happy to know how safe it was. I've been dealing with Sam (property manager)back and forth thru emails with questions and she responds back right away. She has been a great pleasure to deal with. The condo is huge, we never felt cramped like a hotel room. all the amenities listed were all there. If you rent a car, there's a parking spot right out front. There was an elevator to get to the 2nd floor. The balcony was spacious. Everything is walking distance from the condo. The balcony faces the pool. The beach is right across the street which we used everyday. There's beach chairs to rent from Buccaneers beach bar but lf you are ordering something from them it's free. There's a supermarket across the street. (Be prepared, prices were quite high but it's more for the convience) We didnt use the kitchen for cooking, but everything U need is there. The condo is very clean. I must say that we were very pleased and will return!
  • Submitted: Jan 19, 2015
  • Stayed: Jan 2015

Our ultimate Caribbean dream home!

5 of 5
My husband and I stayed at Seabrooke during the week of Jan 4th thru the 11th with two other couples. Broker/caretaker Wendy was amazing from beginning to end, she arranged every detail of our stay! The villa was extremely well equipped with a chefs kitchen including granite counter tops. I believe we may have been the 1st group to stay after a major refit as every appliance was new. The house was very clean and beautifully furnished, and with THE MOST AMAZING VIEW we’ve ever experienced on ANY vacation so far. Watching the sunset from our porch nightly; from our bedrooms we could hear the waves lap the beach. We took long walks on Simpson Bay Beach where we discovered many restaurants. I got up early every morning to watch the sun rise, It was truly paradise on earth. The view of the mega yachts on the horizon, a passing rain shower far at sea, a bottle of wine while watching the sky turn the most stunning colors. Additionally, an ATM, restaurants, pharmacy, bakery, grocery store and tons of nightlife were all within walking distance of the house. Seabrooke felt like our ultimate Caribbean dream home. We loved it so much, We are considering re-booking for next year to avoid post-vacation blues.. I could really get used to living like that.
  • Submitted: Jan 15, 2015
  • Stayed: Jan 2015

Beautiful Beach!

4 of 5
Rating Details: I was more than satisfied with the condition of the vacation rental. I was very happy with the location. The vacation rental was very clean. The property manager was very helpful. Overall, I recommend this vacation rental. Reviewer Comments: Had a great time. We were told that the cleaning service would come 3 times a week and they never came. Other than that, everything was great! Awesome beach, great location, short drive to Maho, security at night!
  • Submitted: Jan 10, 2015
  • Stayed: Dec 2014