Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

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

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Save time when booking: choose rentals that accept online reservations or online payments

Islamorada Vacation Rentals with Online Payment(31)

31 Results
$875 - $1,600
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(15)
  • 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 5
7 night minimum stay
(20)
  • 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)
$8,100 - $8,700
per month
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
30 night minimum stay
(5)
  • 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)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(13)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(10)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
(25)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(18)
  • 9 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 25
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(28)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(26)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 16
7 night minimum stay
(5)
5 more choices from the HomeAway Network
$1,825 - $2,300
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(45)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
$2,800 - $3,200
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(6)
Advertisement
 

Recent Islamorada Reviews

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!

5 of 5
Our group consisted of 8 people, 4 adults and 4 children, and the place accommodated perfectly. The house is very well described in that it is very lush and tropical, also including great wildlife (all the kids got to pet a manatee from the dock). Being centrally located was a plus for any north/south excursions. The owner was very responsive with any requests. We all had a genuinely great time and would use again as well as recommend to others.
  • Submitted: Dec 4, 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