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Key West Holiday Rentals

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[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
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 ...
  • Nightly
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  • Weekly
    £300 - £1,345
  • Monthly
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Packer Retreat, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 4
30 DAY MINIMUM RENTALPacker Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to ...
  • Nightly
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  • Weekly
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  • Monthly
    £3,903 - £5,404
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 2
30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a ...
  • Nightly
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  • Weekly
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  • Monthly
    £3,602 - £4,803
Bahama Dreamin', Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 2
30 DAY MINIMUM RENTAL An enchanting island cottage nestled in the quiet end of Old Town in a small private compound with a hot tub and a pool. Set the pace of ...
  • Nightly
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  • Weekly
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  • Monthly
    £2,402 - £3,302
Contact Manager
Nightly rate from
£901
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Min stay:7
In the fabulous Truman Annex enclave and near the Caroline Street walking gate directly to downtown Key West, this nicely decorated home features a thirty ...
  • Nightly
    £901
  • Weekly
    £2,702 - £6,304
  • Monthly
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Contact Manager
Nightly rate from
£150
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay:7
This brand new property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key ...
  • Nightly
    £150 - £240
  • Weekly
    £1,009 - £1,681
  • Monthly
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Beach Club #112, Key West
Contact Manager
Nightly rate from
£156
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:7
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This comforatble 2 bedroom unit features a huge ...
  • Nightly
    £156 - £294
  • Weekly
    £1,051 - £2,059
  • Monthly
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Contact Manager
Nightly rate from
£186
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 2
Min stay:7
In the heart of Old Town, convenient to everything. The condo is set above a brick, tree lined courtyard that includes shops and restaurants. This three ...
  • Nightly
    £186 - £294
  • Weekly
    £1,219 - £2,059
  • Monthly
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Contact Owner
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 - £240
  • Weekly
    £660 - £1,201
  • Monthly
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Contact Manager
Nightly rate from
£120
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:7
Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium complex is situated opposite the largest beach ...
  • Nightly
    £120 - £222
  • Weekly
    £799 - £1,555
  • Monthly
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Lavender Jungle, Key West
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay:7
LAVENDER JUNGLE - Beautiful two bedroom one bath Shipyard condo located in the Truman Annex. This property has a renovated kitchen and upgraded bathroom. For ...
  • Nightly
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  • Weekly
    £300 - £1,345
  • Monthly
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Angela Cottage, Key West
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 2
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
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  • Weekly
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  • Monthly
    £3,002 - £3,903
Contact Manager
Nightly rate from
£357
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 4
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town ...
  • Nightly
    £357 - £477
  • Weekly
    £2,702 - £3,341
  • Monthly
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Beach Club #204, Key West
Contact Manager
Nightly rate from
£156
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Min stay:7
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This is one of the most elegant and colorful 2 ...
  • Nightly
    £156 - £294
  • Weekly
    £1,051 - £2,059
  • Monthly
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Secret Villa, Key West
Contact Manager
Nightly rate from
£270
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 3
Min stay:7
A hideaway on Freeschool Lane This unique villa is hidden away on the end of the quiet lane just a step away from Duval Street. Surrounded by exotic tropical ...
  • Nightly
    £270 - £474
  • Weekly
    £1,807 - £3,320
  • Monthly
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Key West Holiday Rental Advice
Posted by DarkOne, 16 Nov 2009
... KW was a laid back vacation. On the ... ... Interlude over . . . . back to our vacation We unpack ... ... miles a day when on vacation, but it ... ... we have to do on vacation. The good ... ... see a 6 person electric rental car crashed into a fence at Simonton and Caroline. An ambulance is ... more
Posted by SoccermomIA, 17 Nov 2009
... going to Key West in February for a vacation. Is this a good place (things to do) for kids, age range is 7-13yrs? Also, any ideas on where to stay, rental or hotel? What is the average temp in February? Kids like to snorkel, boogie board, etc. Thanks everyone ... more
Posted by bluewater, 17 Nov 2009
... perfect place for a family vacation! There is ... ... look into a house/condo rental. Also - plenty of resorts that have nightly rentals with kitchens/living rooms etc. If you're hesitant on KW - which I don't think you should be, but still want to be in the Keys - take ... more
Posted by dwass690, 17 Nov 2009
... private beaches and water sport rentals on property. Don't be detered by the people who tell you KW is not for Kids. These people assume you don't know it's wrong to have your kids out all night and maybe they feel uncomfortable around kids because they don ... more
Posted by brodieDublin, 11 Nov 2009
... is actually a really good choice. A cheaper room with a share bathroom may be avaialable. We balked at the shared bathroom option but is actually fine and very do-able!!! Your other option is a vacation rental. You could try www.vacationrentalskeywest.com to check rentals. Enjoy your trip ... more
Posted by ddpepper72, 11 Nov 2009
... daily housekeeping like in other rentals so we had to clean up after ourselves. Not a big deal but not everyone wants to clean on their vacation. - It is a residential area so there wasn't as much opportunity to meet neighbors like at a b&b. - We got a ... more
Posted by ohbo, 11 Nov 2009
... factor. if something goes wrong (dishwasher breaks, AC breaks), how does it get corrected? these little things are the one advantage of renting through a rental operation rather than from the owner, but there are lot of reputable owners and many are listed in the "vacation rentals" section above left ... more
Posted by ohbo, 11 Nov 2009
... to the Compass Realty weekly rentals. Scroll down to the Truman Annex section and you will see a plethora of options. The Harbor Place units are further down the page in the Truman Annex section. Compass also provides a nice map of Truman annex on their home page under "neighborhoods ... more
Posted by ybbhomeless, 7 Nov 2009
... in the living room and two bedrooms and the house is furnished with anything you could possibly need during your stay. The pool is very nice. Here is the link: http://realadventures.com/listings/1025334_Island-Wind-Key-West-Vacation-Home-Rentals Truman Annex is another place you could look ... more
Posted by brodieDublin, 7 Nov 2009
Try www.vacationrentalskeywest.com - they have a variety of rentals to choose from. We always stays in Bahama Breeze, which I highly recommend! http://www.tripadvisor.com/VacationRentalReview-g34345-d1456401-Bahama_Breeze-Key_West_Florida_Keys_Florida.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