38 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Simpson Bay Vacation Rentals(38)

38 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(17)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 7 night minimum stay
(32)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
5 - 10 night minimum stay
(13)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(18)
$500 - $600
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 7 night minimum stay
2 Reviews
$2,975 - $5,500
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(4)
$229 - $329
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 7 night minimum stay
(9)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
(4)
$215 - $300
per night
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 3
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(22)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(17)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 6 night minimum stay
(6)
$525 - $929
per night
3 - 10 night minimum stay
  • 2 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 10 night minimum stay
(3)
  • 4 BR,
  • 5 BA,
  • Sleeps 12
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(7)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
1 Review
$1,225 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(7)
$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)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 Review
15 more choices from the HomeAway Network
$175 - $235
per night
1 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 4 night minimum stay
(5)
$350 - $750
per night
3 - 10 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
3 - 10 night minimum stay
(16)
$357 - $500
per night
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
$1,750 - $3,300
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(9)
$1,050 - $1,750
per week
7 night minimum stay
  • 1 BR,
  • 1 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)
$1,100
per week
7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
Advertisement
 

Recent Simpson Bay Reviews

This property is awesome!

5 of 5
This property is a five star for sure! Great location right on the beach, all amenities were there. Theo was most helpful and we took a boat trip to two snorkelling places which was one of the highlights. There are two restaurants within walking distance if you don't feel like cooking and a great kitchen if you do. Town is 5 minutes away with great places to eat as well. Recommend renting a vehicle. Hope to come back next year!
  • Submitted: Jan 28, 2015
  • Stayed: Nov 2014

Amazing Villa! Best vacation ever!

5 of 5
My family and I (11 of us including, 2 grandmothers and a 4 year old) just returned from a 1 week stay over the New Year at this beautiful villa. It was everything we expected and more. We were amazed when we walked in the doors and saw the beauty of this villa and the scenery from the backyard. It was spacious for all of us and the upstairs allowed for the extra space needed for the family. Waking up to the sunrise every morning was beautiful. The space in the backyard allowed everyone to do their own thing and to have family dinners while enjoying the weather and view. The sights of the fireworks on New Years Eve was spectacular and seeing all the beautiful yachts pass by was breathtaking. The Villa was in the most perfect and convenient location for our family. A 10 minute walk took us to the sunset bar for breakfast or to relax on the beach and a 10 minute walk in the other direction took us to Simpsons Bay Beach that was never crowded. Jenny was so inviting when we first got there and shared a lot of useful information on where to buy food, drinks, etc. We were also pleasantly surprised to get a visit from Rick when he was in the area and he was able to share more useful information for us on what to see and where to go. Being close to the airport was nice and we were never bothered by the noise. This was our first villa rental as my family normally does all inclusive resorts and hands down it topped every family vacation we have been on. To be able to have the space and privacy of the villa was a great feature and there was so much to do and see. Thank you Rick for sharing your beautiful home with us and we can't wait to come back on our next trip to St. Maarten. You made our end to 2014 and beginning to 2015 the most memorable and relaxing time ever!!
  • Submitted: Jan 19, 2015
  • Stayed: Dec 2014

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