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Key West Holiday Rentals

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Recommended by Travellers

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Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Packer Retreat, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 4
Min stay:30
30 DAY MINIMUM RENTALPacker Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    CAD5,617 - CAD9,191
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Contact Manager
Nightly rate from
CAD204
map unavailable
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:7
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and ...
  • Nightly
    CAD204 - CAD378
  • Weekly
    CAD1,358 - CAD2,645
  • Monthly
    --
Albury Bungalow, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:30
30 DAY MINIMUM RENTAL ALBURY BUNGALOW A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    CAD3,574 - CAD6,638
Angela Cottage, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:30
30 DAY MINIMUM RENTAL ANGELA COTTAGE This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    CAD3,574 - CAD6,638
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay:30
NEW SINCE JANUARY 2010 - MONTHLY RENTAL ONLY! Located in the old town of Key West CARPE DIEM is a quintessential Conch Cottage close to all attractions Key ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    CAD2,247 - CAD4,085
Contact Manager
Nightly rate from
CAD179
map unavailable
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Boater's Dream, Key West
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    CAD3,163 - CAD5,106
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Contact Manager
Nightly rate from
CAD179
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just ...
  • Nightly
    CAD179 - CAD203
  • Weekly
    CAD1,251 - CAD1,787
  • Monthly
    CAD5,361 - CAD6,449
Key West Holiday Rental Advice
Posted by CaptBonez, 11 Mar 2010
... He sold out a few years back before the crash and bought a place up the coast. I'm going to have to let him know its a vacation rental now. Fish hard, Bonez Does it have a web site or a page on-line I can forward to him ... more
Posted by MrsO531, 23 Feb 2010
the vacation rental website has lots of great ideas, thanks! ... more
Posted by simkeith, 22 Feb 2010
... with a B&B or vacation rental condo rather than a hotel or resort. I was in Key West in August of 2008 and a very very minor tropical storm came rolling through. An evacuation order was given by the politicians, which means you have to leave and it is ... more
Posted by evhudsons, 16 Feb 2010
You might want to get a vacation home rental, like the Truman Annex. Just google Truman Annex vacation rental and check it out, or look through Trip Advisor for Truman Annex. They are week or longer rentals. ... more
Posted by xaos, 13 Feb 2010
Not sure if it still is but that house Arnie is refering to used to be available as a vacation rental. ... more
Posted by goldilox2677, 4 Dec 2009
... Thanksgiving in a Bone Island vacation rental on Whitehead St. (Little Palm) and it had BED BUGS. I have 58 welts all over my body. I contacted them via email with pictures and no reply. My husband called the office and someone said we must have brought them from home ... more
Posted by goldilox2677, 4 Dec 2009
You are right Arnie. I am pretty much an expert on bed bugs after this happened to me. One is never the same after something like this. I will check every inch of every hotel room and vacation rental from now on. ... more
Posted by bone-island, 7 Dec 2009
... the owners of Bone Island Vacation Rentals we ... ... complaint passed to Bone Island Vacation Rentals. 2. Upon receipt of the complaint a pest control company inspected the unit and no infestation of any type was found. Of course we conducted our own inspection with the same results. 3. As a ... more
Posted by kittenkatt79, 25 Jan 2010
I think a private vacation rental (rental house ... ... contact with Vacation Homes of Key West - http://www.vhkw.com - for a family reunion trip this year. Also check out http://www.vrbo.com for vacation rental houses listed by the owner. I've found negotiating can be easier through VRBO ... more
Posted by djad, 24 Jan 2010
TA has aTimeshare Vacation rental forum. I have not used it to rent anything, but may help. http://www.tripadvisor.com/ShowForum-g1-i10700-Timeshares_Vacation_Rentals.html ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus 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
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns