42 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Islamorada Short Term Vacation Rentals with Online Payment(42)

42 Results
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(7)
  • 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
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
$950 - $1,600
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(14)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(14)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(13)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(17)
$1,800 - $3,000
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(4)
$2,500 - $3,000
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(9)
$395 - $700
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 3 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(28)
$107 - $200
per night
6 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
6 - 7 night minimum stay
(5)
$2,100 - $2,700
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(3)
$1,495 - $1,995
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(15)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(7)
  • 5 BR,
  • 3 BA,
  • Sleeps 15
28 night minimum stay
2 Reviews
  • 8 BR,
  • 5 BA,
  • Sleeps 24
2 Reviews
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
30 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
$1,099 - $1,499
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(3)
$5,300 - $6,200
per week
7 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(8)
$5,500
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
1 Review
Advertisement
 

Recent Islamorada Reviews

Beautiful Unit

5 of 5
The duplex is tastefully decorated. The kitchen well stocked for preparing our meals. Loved the roof top for viewing the sunrise and sunsets!! There is a small pool which was never crowded. Could the grounds and beach area be in better shape, yes, however this unit makes up for it.
  • Submitted: Mar 16, 2015
  • Stayed: Mar 2015

Amazing - simply amazing

5 of 5
Mike said we wouldn't be disappointed and boy was he right. We just checked-in and EVERYTHING is beyond expectations!!! Beautifully decorated, super clean (for all you OCD people like me) and more amenities than we thought. I'll check back in at the end of the week but so far - 5 star!!!!!!
  • Submitted: Mar 14, 2015
  • Stayed: Mar 2015

Wonderful Stay in the Keys!

5 of 5
Very nice condo that has updated bathrooms and kitchen! Close to everything...very nice pool and area at the waters edge! Could see the water and spectacular sunsets from the condo balcony! We met Pete when he stopped by to drop something off. Wonderful person, easy to work with and wonderful condo lead to an awesome stay in the Keys! You won't be sorry to rent this condo! THANKS, PETE!
  • Submitted: Mar 3, 2015
  • Stayed: Feb 2015