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Key West Holiday Rentals

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[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Nightly rate from
£240
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 10
Bathrooms: 4
Built in the 1880's and located just steps from Duval Street, this large historic building includes a great room with vaulted ceilings encompassing the living ...
  • Nightly
    £240 - £366
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Nightly rate from
£105
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 3
Min stay:3
All new 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse ...
  • Nightly
    £105 - £241
  • Weekly
    £662 - £1,204
  • Monthly
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 3
This beautiful 3-story town home is located in the gated Truman Annex in the historic Foundry. From the house, it's an easy to walk to the beach at Fort ...
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  • Weekly
    £970 - £1,509
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Porter Court, Key West
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 5
Bathrooms: 2
Located at the prestigious Truman Annex this lovely two bedroom, two bath vacation rental town home is convenient to everything. This hideaway is within ...
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  • Weekly
    £1,084 - £1,807
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
This classic 1920's Conch house is just four blocks from the North end of Duval Street. Relax on the front porch or float in the pool. The house features ...
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  • Monthly
    £3,011 - £9,034
Shipyard, Key West
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 5
Bathrooms: 1
These shipshape condominiums have gorgeous landscaped yard and deck areas for entertaining and sunning. Located at the Truman Annex, just two blocks from ...
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  • Weekly
    £696 - £1,265
  • Monthly
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Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 3
Min stay:7
Place in Paradise - Experience the finest in Key West living when you stay in this delightful two bedroom two and one half bath conch-style townhome in ...
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  • Weekly
    £301 - £1,867
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Heron, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 1, sleeps 4
Bathrooms: 1
Heron. These cottages are some of several cottages located at the Colony cottages, formerly the Colony Guest House. These one bedroom one bath accommodations ...
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  • Weekly
    £301 - £1,427
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Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 3
Our guests will find this impressively detailed treasure in the Historic Seaport District. Circa mid 1850's, this home is in the center of the most historic ...
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  • Monthly
    £2,409 - £6,022
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 3
Located just within the gates of Truman Annex, this townhouse is only a short walk to the beach at Fort Zachary Taylor State Park; the sunset celebration at ...
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  • Weekly
    £991 - £1,475
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay:7
SHIPYARD TREASURE - Great Key West location, this two bedroom one bath Shipyard condo has it all. You are centrally located to all the sites and attractions ...
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  • Weekly
    £301 - £1,349
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Seaside Place, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 5, sleeps 12
Bathrooms: 4
This beautiful five bedroom, four bath home located just a block away from the Southernmost Point in the continental USA. Beaches are just a few minutes away ...
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  • Weekly
    £3,035 - £4,201
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Management: Professional
Property: Condo/Apartment
Bedrooms: 1, sleeps 3
Bathrooms: 1
This quaint conch duplex sits on the edge of "The Meadows" area of Old Town Key West. This one bedroom one bath is one of the few one-bedroom homes that ...
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  • Monthly
    £1,506 - £3,011
Rainbow's End, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 2
RAINBOWS END Charming 2 bedroom 2 bath single family home with a private pool in Old Town Key West. This breezy single family home is centrally located near ...
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  • Weekly
    £301 - £2,183
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:7
BEACH HOUSE CONDO – Is a beautiful two bedroom two bath Shipyard condominium with a private Jacuzzi on the back patio. Located in the Truman Annex which is ...
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  • Weekly
    £434 - £1,518
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Key West Holiday Rental Advice
Posted by L164, 30 Oct 2009
... for many years) in January and would like to know if anyone knows of a rental with a kitchen and a sunset view near Mallory Square. We would also consider a hotel/bb with a sunset view that includes breakfast.. Is this too much to ask for in Key West ... more
Posted by ybbhomeless, 30 Oct 2009
... viewing up a spiral staircase on its rooftop patio. This is a one of a kind condo. The Galleon has 5 floors. In this condo YOU ARE THE 6th FLOOR! We loved it there. It is a great location on Front Street. http://www.vacationrentals.com/vacation-rentals/23760.html ... more
Posted by brodieDublin, 1 Nov 2009
Variety of rentals available from www.vacationrentalskeywest.com but don't know if any have a sunset view??? ... more
Posted by dmilbury, 21 Oct 2009
I noticed an increase on Craig's list in the vacation rental section for FF week also. ... more
Posted by sevenelevenohnine, 27 Oct 2009
... I've found that most rentals have a ... ... the person whose name the rental would be in, or anyone staying there? I did see that some of them said that any occupant under 25 had to be with a parent/legal guardian/family group. Would being with a spouse satisfy ... more
Posted by UNCMickey, 27 Oct 2009
... above posts. I own a vacation rental; sadly not in the Keys! If someone is up front with me about a special situation/request, I'm almost always willing to work with them. --BTW, I was 25 on my first trip to KW, it was my honeymoon! (21+ years ago ... more
Posted by Trimada, 23 Oct 2009
... into Ft Lauderdale: Picked up rental, we were ... ... purpose, (hey we’re on vacation) left about ... ... 7 year old for a “vacation”. This is ... ... them but when taking a vacation, go to ... ... I am talking about full vacation 5-7 days, if you are stopping off on a cruise for ... more
Posted by jaywepp17, 24 Oct 2009
... just a "different" sort of vacation spot. Certainly nothing will compete with Disney for a kids trip, but in Key West you can do so many uinique things that get them up and active. But agreed with most of the rest of the report. Glad you had a good time ... more
Posted by Trimada, 25 Oct 2009
... use my hotel points for vacations. I am with you entirely packing up and go each night is not ideal but it saved a lot of $$ Without a doubt I am sorry we didn’t get to the CTH, it was my biggest regret but as you say, it gives ... more
Posted by SDT, 23 Oct 2009
... want to be sure the rental is legal or you could end up with a pretty lousy vacation. All houses and condos are required to have transient licenses or they can not rent for less then 30 days. You might have found a great deal, but I would take a ... 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