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Cudjoe Key

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Vacation Rentals in Cudjoe Key, 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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18 Trusted Cudjoe Key Area Rentals
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
1-18 of 18
A tropical paradise in the florida keys, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
A tropical paradise in the florida keys
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
133 AUD - 220 AUD
Week:
924 AUD - 1,539 AUD
Month:
3,079 AUD - 3,592 AUD
Minimum rental - 1 week
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Lower Keys Paradise- 2/2 on water near Key West, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Lower Keys Paradise- 2/2 on water near Key West
Slideshow
4.5 of 5 stars 6 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
924 AUD - 1,026 AUD
Minimum rental - 3 nights
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Tropical Paradise Oceanfront Home with Pool, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Tropical Paradise Oceanfront Home with Pool
Slideshow
4.5 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
338 AUD
Week:
2,360 AUD
Minimum rental - 1 night
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Beautiful spacious home with pool and ocean views, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Beautiful spacious home with pool and ocean views
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Month:
5,131 AUD - 6,158 AUD
Minimum rental - 1 week
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White Ibis Inn, Oceanview Private Estate, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
White Ibis Inn, Oceanview Private Estate
Slideshow
4.5 of 5 stars 10 reviews
  • Holiday Rental House
  • 6 Bedrooms, sleeps 14
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
530 AUD
Week:
3,489 AUD - 4,310 AUD
Minimum rental - 5 nights
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Oceanfront 5 star Home Beach area Heated Pool, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Oceanfront 5 star Home Beach area Heated Pool
Slideshow
4.5 of 5 stars 13 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
359 AUD
Week:
1,847 AUD - 3,028 AUD
Minimum rental - 1 week
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Family Retreat Oceanfront Home with Pool, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Family Retreat Oceanfront Home with Pool
Slideshow
3.5 of 5 stars 1 review
  • Holiday Rental House
  • 6 Bedrooms, sleeps 12
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
440 AUD
Week:
3,079 AUD
Minimum rental - 1 night
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Oceanfront Tropical Paradise Vacation Home, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Oceanfront Tropical Paradise Vacation Home
Slideshow
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Check availability
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Fandango, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Fandango
Slideshow
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
440 AUD
Week:
3,079 AUD
Minimum rental - 1 night
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The following rentals are within 10 kilometres of Cudjoe Key, Florida Keys, Florida.

Little Sleeves End, Little Torch Key
Florida, Florida Keys, Little Torch Key Holiday Rentals
Little Sleeves End
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
205 AUD
Week:
1,334 AUD
Month:
5,131 AUD
Minimum rental - 4 weeks
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Florida Keys Waterfront Getaway, Ramrod Key
Florida, Florida Keys, Ramrod Key Holiday Rentals
Florida Keys Waterfront Getaway
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
205 AUD
Week:
1,437 AUD
Month:
3,695 AUD
Minimum rental - 1 week
Check availability
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Island Living, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Island Living
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
292 AUD
Month:
5,131 AUD
Minimum rental - 1 night
Check availability
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Secluded Hideaway, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Secluded Hideaway
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
235 AUD
Week:
1,642 AUD
Minimum rental - 1 night
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Oceanfront Rental on Summerland Key, Florida, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Oceanfront Rental on Summerland Key, Florida
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
2,258 AUD
Month:
6,158 AUD
Minimum rental - 1 week
Check availability
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Barry Beach - 4/3 Keys Cottage, Open Water, Pool, Little Torch Key - JUST ADDED
Florida, Florida Keys, Little Torch Key Holiday Rentals
Barry Beach - 4/3 Keys Cottage, Open Water, Pool
Slideshow
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
513 AUD
Week:
3,079 AUD
Month:
8,210 AUD
Minimum rental - 3 nights
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Oceanfront Estate on Beautiful Summerland Key, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Oceanfront Estate on Beautiful Summerland Key
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
2,566 AUD - 4,618 AUD
Month:
7,697 AUD - 13,855 AUD
Minimum rental - 1 week
Check availability
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Pool, Dock, Sandy Beach, Privacy, Open Water, Summerland Key, FL - JUST ADDED
United States, Florida, Summerland Key Holiday Rentals
Pool, Dock, Sandy Beach, Privacy, Open Water
Slideshow
  • Holiday Rental House
  • 7 Bedrooms, sleeps 14
  • 5 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
1,026 AUD
Week:
5,644 AUD
Month:
20,525 AUD
Minimum rental - 3 nights
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Ocean Front with Private Boat Basin and Pool, Little Torch Key - JUST ADDED
Florida, Florida Keys, Little Torch Key Holiday Rentals
Ocean Front with Private Boat Basin and Pool
  • Holiday Rental House
  • 6 Bedrooms, sleeps 12
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
667 AUD
Week:
3,592 AUD
Month:
13,342 AUD
Minimum rental - 3 nights
Check availability
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1-18 of 18

Cudjoe Key Holiday Rental Advice

Key West Vacation Rentals
Posted by brodieDublin, 20 Jan 2012
www.historichideaways.com www.athomeinkeywest Or check holiday Rentals to the left! ... more
kays in april
Posted by flipflopsrule, 8 Jan 2012
Contact Andi Saylor at Keys Holiday Rentals. ... more
Is TravelFurnish.com a reputable agency?
Posted by jess j, 11 Feb 2012
... whole experience renting from a vacation rental by ... ... that people think renting a vacation rental by owner is like going to a hotel and it is not. When I checked in I was told that this condo does not operate like a hotel. The owners here are renting them out ... more
Posted by Julius C, 20 May 2012
... was trying to find a vacation rental through flipkey, and found this gorgeous apartment in Times Square area for 259/night, so I decided to ask for the availability. The owner/host Dave Jennings replied back with a gmail account (tripolot@gmail.com) and linked me to travelfurnish.com for ... more
Friends of Bill Wilson
Posted by Stephen H, 30 Apr 2012
Any friends of Bill Wilson renting Condo? We are 4 non-drinkers, non-smokers looking for vacation rental with 2 BR and 2 BA 8/11/2012 - 8/18/2012. Thanks & Peace! ... more
Chosing where to stay for 1 week, help!
Posted by bluewater, 30 Apr 2012
No all inclusives (except Little Palm Island). A resort or vacation rental? That's really up to you and what you like and don't like. It's best to stay with what you like. You can wander at will with a resort too. ... more
dove creek lodge, key largo marriott, or hampton inn
Posted by Kimdrake26, 23 Apr 2012
Check out the vacation rentals on TA, My boyfriend and I went in this same circle trying to choose betwene these 3 hotels (none looking too spectacular, especially for the price they wanted!). Out of curiosity I started looking at what a vacation rental would cost. We wound up booking ... more
Posted by wnbamiamisol, 24 Apr 2012
Vacation rentals (houses) in unincorporated Monroe County are regulated by law to a 30 day minimum. Some condos are excluded as are some gated communities. If you go that route, best to make sure yours is a legal short term rental rather than have your vacation turn into a disaster. ... more
Absolutely Paradise, Vacation Rental Home Key West
Posted by TravelAgent026, 22 Mar 2012
Wonderful property...house is very nice...3 bedroom...2 1/2 baths...pool was ok...within walking distance of South beach and Duval St. Bone Island Vacation Rentals...very nice! ... more
Best area for a house rental?
Posted by SDT, 10 Mar 2012
... They will help you get what you want and assure the house has the needed license to be able to be rented short term. Compass Realty has many properties in Truman Annex. Historic Hideaways is another choice, but if you google "Key West Vacation Rentals" you will see several agencies ... more
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