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Islamorada Long Term Vacation Rentals with Online Payment(43)

43 Results
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(15)
$1,575 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(12)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(10)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(10)
$2,500 - $3,000
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(6)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(6)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(3)
$1,600 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(13)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(33)
  • 9 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 25
7 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 8
(25)
$1,150 - $1,400
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(14)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(26)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
(11)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
$12,900
per month
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 8
28 night minimum stay
2 Reviews
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(5)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
2 Reviews
$4,800
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(7)
$2,100 - $2,800
per week
7 - 28 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 - 28 night minimum stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 15
28 night minimum stay
2 Reviews
$5,300 - $6,200
per week
7 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
$140 - $199
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
$14,000
per month
28 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
28 night minimum stay
(5)
$2,970 - $6,000
per month
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
28 night minimum stay
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Recent Islamorada Reviews

The Perfect Family Rental in the Florida Keys

5 of 5
Anyone looking to experience a TRUE 5 Star rental in the beautiful Florida Keys need not look further. Our family (of 16) spent our Thanksgiving holiday at this beautiful villa and it exceeded ALL our expectations. Everyone agreed that the location, accommodations and overall assistance from the property owner regarding local contacts made this selection for our "Three Generation Vacation" a most memorable holiday, one our family will not soon forget. The owner provided us with names of people who we used during our stay. Including a private chef and his assistant who came to the villa and prepared several evening meals. (A luxury when you have toddlers and don't necessarily want to dine out every night) He provided us with the name of a car service to pick us up from the Miami airport. He was also helpful in giving us a list of places to see and go (including deep sea fishing) and the infamous Theater of the Sea. Great day time activity for the kids. There was also someone there at the villa to greet us (upon our arrival) and to familiarize us with the property. And if we needed any assistance during our stay that same person was only a phone call away. The most impressive quality with this property is that you not only have this beautiful, custom tiled pool and Jacuzzi but also your own private beach. This property is pristine, comfortable, spacious and provides you with all the comforts of home. The landscaping is picture perfect, so much so that we hired a professional photographer to take our family portrait on the beautiful grounds. The master suite was grand and provided you with privacy and beautiful views of the ocean and sunsets.. An elevator was useful for taking luggage to each of the rooms. The bedrooms were extremely comfortable and the outdoor showers off each of the 4 main bedrooms, were an added bonus. The Pineapple house is a perfect spot for the person who wants a little privacy and the guest house is wonderful for a family to share. The house is beautifully decorated with the kitchen being more professional than residential. Our family could not have been more comfortable and pleased with our week spent at this beautiful "home away from home". Overall, this property gets 5 STARS!
  • Submitted: Dec 21, 2014
  • Stayed: Nov 2014

Wonderful Location

5 of 5
It was our 1st time in Islamorada. Knowing very little about the location, we blindly made the decision to rent in Anglers Reed. We made a great decision. The place was great. We found out that much of the Keys was built many moons ago. Many of buildings are old...not Anglers Reef. I am guessing it's about 8 years old. It's small (50 ish houses) and very quaint. The pool is wonderful. I think they keep it at about 90 degrees! The marina can handle boats up to 30 feet. And the beach is small, but nice. This unit is in a wonderful location. A quick walk to the pool, marina or beach. The neighborhood is tucked away, but close to a few watering holes/ restaurants. We had 2 adults and 3 kids (one in a pack and play)...and the unit size was perfect. The unit was very clean when we arrived and had everything we need for the week. We have already reached out to the owner about renting it again!
  • Submitted: Dec 5, 2014
  • Stayed: Nov 2014

Great place, great time!

5 of 5
This was a wonderful trip! We stayed here last year with our dog and loved the location! The owner answered all my questions prior to my visit. It's off the beaten path and nice and private. We returned to find the same! There is road construction ongoing on the main road and you don't hear anything back here. The condo has everything you need. Very clean and stocked well in the kitchen. We fished from the dock and saw many varieties of fish. Lots of fun. We will hopefully be able to return next year!
  • Submitted: Nov 20, 2014
  • Stayed: Nov 2014