20 Best Cudjoe Key Vacation rentals on Holiday Lettings - House rentals

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Cudjoe Key

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24 Vacation rentals

13

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 mi …see more

from $260 / night

$1495 - $2250 / week

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Responds fast!
avg. 2 hours 12 minutes

from $260 / night

54

Vacation home rental

Florida Keys / Cudjoe Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size …see more

from $158 / night

$1100 / week

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from $158 / night

25

Vacation cottage in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 23 mi
  • Swimming pool
Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, livi …see more

from $140 / night

$890 - $1400 / week

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Responds fast!
avg. 2 hours 44 minutes

from $140 / night

(3) Very Good 

19

Cudjoe Key Vacation home accommodation

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing …see more

from $94 / night

$654 / week

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Responds fast!
avg. 3 hours 14 minutes

from $94 / night

15

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Come enjoy the best the Florida Keys has to offer, with this lovely 3 bedroom and 2 bathroom canal front home on Cudjoe Key! This nautically decorated, comfortable home offers quick boating access to Cudjoe Bay from the 40’ dock and is fully equipped for the water enthu …see more

from $114 / night

$794 / week

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from $114 / night

11

Vacation cottage in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. …see more

from $149 / night

$999 - $1099 / week

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from $149 / night

19

Cudjoe Key Vacation home rental

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
This home is great for families! It has been recently updated with new tile throughout, new furnishings and bedding, and features 3 bedrooms and 2 bathrooms as well as a roomy loft area. You'll enjoy an open living plan with a nice size full kitchen with plenty of count …see more

from $134 / night

$934 / week

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from $134 / night

11

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Dreaming of an awesome Florida Keys vacation? This is your perfect pick! This Cudjoe Key home has everything you could wish for and a perfect vacation spot! The home is designed with rich and warm wood tones making it the perfect place to relax after a long wonderful da …see more

from $127 / night

$887 / week

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from $127 / night

14

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Welcome to Egret's Landing! From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style home promises all the comforts of home, and so much more! The 40' dock and yard is landscaped with native foliage and offer …see more

from $100 / night

$700 / week

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from $100 / night

16

Cudjoe Key Vacation home rental

Florida Keys / Cudjoe Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
It's always 5 O'Clock here at this wonderful Florida Keys vacation spot. Start your day off with refreshing Mimosas or Bloody Marys as you enjoy sitting out on the screened porch overlooking the nice boating canal. The interior is nicely decorated in tropical island sty …see more

from $87 / night

$607 / week

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from $87 / night

14

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Welcome to Cudjoe Cottage, a wonderful spot to spend your Florida Keys vacation! This 2 bedroom 2 bath home, nestled among lush landscaping, is delightfully decorated in neutral tones with beach accents. The kitchen is completely equipped for the most ardent of chefs, w …see more

from $114 / night

$794 / week

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from $114 / night

12

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate Island home. Home-away-from-home comforts include central air and a well equipped kitchen. The 30' dockage area provides quick and easy access to the …see more

from $97 / night

$677 / week

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from $97 / night

14

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine. Just minutes from Cudjoe Gardens marina for gas, bait and your fishing needs. Deep draft boating will accommodate up to 4 foot draft. Large and …see more

from $120 / night

$840 / week

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from $120 / night

19

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for friends to gather. Ful …see more

from $180 / night

$1260 / week

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from $180 / night

28

Home rental in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
CANAL FRONT HOME WITH 3 BEDROOM AND 2 BATH AND POSSIBLE 4TH BEDROOM , TWO ENTRANCE HOME ONE TO LIVING ROOM AND OTHER TO COVERED DECK OVERLOOKING CANAL. GLASS SLIDERS TO BEAUTIFUL VIEWS OFF 2 BEDROOMS . ALL NEW FURNITURE AND STAINLESS STEEL APPLIANCES, GRANITE COUNTE …see more

from $167 / night

$1167 / week

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from $167 / night

8

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This Cudjoe Key home is neat as a pin. Brand new in 2007 with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get togethers. The large comfortable living room has plenty of seating including recliners in the sofa and l …see more

from $90 / night

$630 / week

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from $90 / night

19

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front home is very comfortable and spacious. This home offers a living-dining-kitchen great room floor plan with comfortable seating and a flat s …see more

from $95 / night

$665 / week

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from $95 / night

16

Vacation home rental

Florida Keys / Cudjoe Key

3 5 30 nights min

  • 3 bedrooms
  • Sleeps 5
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Come and enjoy the wonderful Florida Keys lifestyle at Tropical Bay. Located at mile marker 22, close to Key West and Marathon for great day trips around the islands. This spacious 3 bedroom, 2 bathroom ground level home is cozy and comfortable. Extra large screened por …see more

from $84 / night

$584 / week

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from $84 / night

34

Home rental in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
AS PER MONROE COUNTY RENTAL LAWS ONLY ONE RENTAL IS ALLOWED PER MONTH TO ONE GROUP OR FAMILY PER 28 Day period. The minimal rental is a WEEK but once you book a partial month, the entire month is to be blocked off. THESE are not our laws but laws from MONROE count …see more

from $428 / night

$2995 - $3300 / week

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from $428 / night

12

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
This great Vacation Home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living & dining rooms provide ideal entertaining areas for friends and family. Enjoy warm, tropical breezes on the large wood dock, overlooking the deepwater canal …see more

from $100 / night

$700 / week

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from $100 / night

12

Vacation caravan/mobile home in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to either the Atlantic or the Gulf. This home has everything you need to enjoy a relaxing vacation with resort amenities at your backdoor. Featuring 2 bedroo …see more

from $135 / night

$851 - $1250 / week

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from $135 / night

15

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating access and cruise out to …see more

from $70 / night

$490 / week

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from $70 / night

20

Cudjoe Key Vacation home rental

Florida Keys / Cudjoe Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
2 Bedroom 2 Bath Sleeps 6 Tropically Decorated Stilt Home Lovely Covered Porch with Water View You won't be disappointed in the beautiful decorated 2 Bedroom/2 Bath stilt home with a canal view. Relax on the covered deck with privacy palms. Lovely tropical decor with …see more

from $120 / night

$900 / week

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Responds fast!
avg. 1 hour 38 minutes

from $120 / night

11

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! The kitchen is fully equipped with all the luxuries of home (and more!). The dockside Tiki Hut and hammock overlook a great, deepwater canal perfect for boating and swimming. …see more

from $167 / night

$1167 / week

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from $167 / night

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