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Islamorada

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Vacation Rentals in Islamorada, Florida Keys

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Tip: Refine your search by price, amenities, & more (see left column).
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134 Trusted Islamorada Rentals
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€527 - €753 / week
3 Bedrooms, sleeps 6
2 Bathrooms
€181 / night
2 Bedrooms, sleeps 4
2 Bathrooms
€527 - €670 / week
1 Bedroom, sleeps 4
1 Bathroom
€376 - €452 / week
Sleeps 4
1 Bathroom
€3,387 / week
5 Bedrooms, sleeps 8
4 Bathrooms

Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Month:
€2,107
Minimum rental - 4 weeks
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
€1,325 - €1,821
Month:
€3,763
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Week:
€2,258
Minimum rental - 1 week
Check availability
Also consider
€527 - €753 / week
3 Bedrooms, sleeps 6
2 Bathrooms
€181 / night
2 Bedrooms, sleeps 4
2 Bathrooms
€527 - €670 / week
1 Bedroom, sleeps 4
1 Bathroom
€376 - €452 / week
Sleeps 4
1 Bathroom
€3,387 / week
5 Bedrooms, sleeps 8
4 Bathrooms
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Month:
€3,010 - €3,387
Minimum rental - 4 weeks, 2 nights
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
€1,129 - €1,242
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
€1,129 - €1,242
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Week:
€1,054 - €1,490
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
€2,258
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
€1,093 - €1,502
Month:
€3,763
Minimum rental - 1 night
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
€1,053
Month:
€2,632
Minimum rental - 1 week
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
€1,129 - €1,505
Month:
€3,387 - €4,515
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 3 Bedrooms, sleeps 1
  • 1 Bathroom
  • Professional
EMAIL AGENT
Month:
€3,010
Minimum rental - 4 weeks, 2 nights
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Month:
€3,010
Minimum rental - 4 weeks, 2 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
€527
Month:
€1,355
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Islamorada Holiday Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
€903 - €1,242
Minimum rental - 1 week
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
€263 - €414
Week:
€1,580 - €2,634
Month:
€5,268 - €9,933
Minimum rental - 1 week
Check availability

Islamorada Holiday Rental Advice

Posted by saramo2, 27 Dec 2010
... for a nice 1 week vacation rental somewhere in the keys, have never been to the keys before. Only needs to sleep 2 (my husband and I) for somtime in May '11. Looking in the price range of about $2000 or less for the week. Hoping for something private like ... more
Posted by bluewater, 6 Feb 2011
... is Futura is only avl by the week, where as KT is avl for whatever your need. And being a nightly you have the daily towel exchange trash out etc - which does make for a price difference. Thats why it's hard to compare nightly prices to a vacation rental ... more
Posted by bluewater, 6 Feb 2011
I thought they did have a weekly rate, can't recall, but still, they have daily service unlike a vacation rental. Something to consider when thinking about rates. you may not care about that, but you can't poo poo it when you compare rates. ... more
Posted by PrincessPalmTree, 12 Jan 2009
... member joining us at our vacation rental in Islamorada and she will be coming down from West Palm Beach. The Greyhound bus schedule appears to be the most straight forward path with one stopover in Miami. My concern is that it is a 2.5 hour layover and my family ... more
Posted by JBSH, 26 Dec 2007
... you are looking for a vacation rental I would call Island Villa Properties or Freewheeler Vacation Rentals they both have a huge inventory of homes to chose from, and I am sure you would be able to find one that is perfect for what you have in mind. Good Luck ... more
Posted by Frivolous, 1 Nov 2008
... very simple wedding at a vacation property in Islamorada in March 2009 but, as some family will be in attendance, I'd like to spend one night away at a romantic hotel somewhere. We have a 2 year old and it'll be the first time I've left her ... more
Posted by Engadiner, 23 Sep 2008
... stayed at the Tackle Shop Apartment at Bud n' Mary's for many years, with a big balcony overlooking the marina and the captain making the best impression on us and the one who brought back the biggest fish with a guarantee has always been Alex Adler / Kalex. Check him ... more
Posted by SRobbo, 15 Jun 2006
... orientated resort and we've booked a 2-bed apartment with ocean view. We're not going until the end of the year but as that's "peak" time we've had to book early! Sorry I can't be of help to you, but good luck with your plans ... more
Posted by dmuso, 8 Sep 2005
... roomy. They have condos and apartments there as well. They have the pool, shuffleboard and it's kid friendly if they are coming with you. People are nice, also there is an awesome fish pond with all kinds of Big fish to feed. We went 5 years ago and are ... more
Posted by mkl2209, 16 Sep 2005
... had the one bedroom oceanfront apartment and it was worth the price. In fact, we'll be there next week! The place is clean, quiet and great for couples or families. The Outback Steakhouse is right next door, and Lazy Days just a few doors down. The area is quiet ... more
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