Cudjoe Key Vacation Rentals

(35 rentals)
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3 BR | 3 BA | Sleeps 8 | Quick View

$234

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

60' of dock, swimmable canal with direct access to cudjoe bay (just 200 yards away). Our home is equipped with a full kitchen and everything needed to relax after a full day of boating. There is a bait freezer, extra storage freezer and ice maker. We also have an extra refrigerator downstairs ...

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Property Type

Cudjoe Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 15 miles to Bahia Honda State Park

$227

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

Minimum Rental is 28 Days to a single family or party (no subleases allowed).PLEASE DO NOT REQUEST for less than 28 night rental. A fine of $16,000.00 is imposed by Monroe county for less than 28 nights. Less than 28 nights is simply non-negotiableNO PETS ALLOWED. IF YOU WANT TO BRING PETS, ...

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Property Type

Cudjoe Key Cottage

"Cudjoe paradise"

A little piece of paradise. From the very moment we arrived we were pleased. Everything was exactly as described and the owners were so helpful and pleasant to deal with. The accompanying boat launch is ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys, ...

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Property Type

Cudjoe Key House

"SPECTACULAR SOUTHERN SUNSET - 5 STARS"

No need for all the little details - this place is just SPECTACULAR! Our stay was absolutely INCREDIBLE! If you're looking for the PERFECT spot for ALL the Florida Keys activities, then this one is a ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every ...

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Property Type

Cudjoe Key House

"Squillets & Manor Wedding"

We had a great time, we will definitely be back! Fun in the sun! Close to restaurants and grocery store.

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 17 miles to Bahia Honda

$317

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

Looking for a vacation rental to get away from it all in the Fabulous Florida Keys? Look no further than our beautifully renovated home with open water and sunset views! This home has three bedrooms and two full bathrooms, open floor plan with designer kitchen and views from every room! You can enjoy ...

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Property Type

Cudjoe Key House

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2 BR | 3 BA | Sleeps 6 | Quick View

4

Distance to beach: 15 miles to Bahia Honda

$501

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on ...

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Property Type

Cudjoe Key House

"Don't worry be happy!!!"

Great location, views were gorgeous from our waterfront decks, 30 mins. to airport! Rental was clean, comfortable & well equipped with everything you need & then some. Home owners thought of everything ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

This vacation home has a spectacular view over Cudjoe Bay to the Atlantic from the upper deck, and from the seats in the heated private pool. Kayaks included in the rental. Home has 4 bedrooms and 2 bathrooms. Property has water access/dock for a small boat, and options to dock a larger or multiple boats ...

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Property Type

Cudjoe Key House

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6 BR | 4 BA | Sleeps 12 | Quick View

$658

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool

About this property

This brand new 5/6 bedroom 4 bath oceanfront home has a private pool and will share dock space, kayaks and the gazebo with Blue Palms Retreat home. There is 1 double and 3 single kayaks. Bring your boat- up to 24’ and your snorkel gear. Relax on one of the porches overlooking The Atlantic Ocean ...

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Property Type

Cudjoe Key House

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2 BR | 3 BA | Sleeps 6 | Quick View

2

Distance to beach: 15 miles to Bahia Honda

$450

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on ...

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Property Type

Cudjoe Key House

"John V"

Susan & Jennifer are great to deal with, this was our 3rd trip to the property, and we can't wait to go back!!

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5 BR | 3 BA | Sleeps 12 | Quick View

2

$658

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Our Cancellation policy is: Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be ...

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Property Type

Cudjoe Key House

"Relaxation"

This property was perfectly located on a quiet street! Great for large family vacation! Loved the views . Only wish is they had a large boat dock for a larger boat ! It’s a must see!

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3 BR | 2 BA | Sleeps 7 | Quick View

$268

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

This 3 bedroom 2 bath home is located on Cudjoe with easy access out to the open water. Bring your boat up to 26`and take out the kayaks provided at this home. There is ample room for outside activities, a BBQ grill and downstairs bait/beverage refrigerator.The master bedroom has a king bed and there ...

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Property Type

Cudjoe Key House

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Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

House - 2 Bedrooms, 2 Bathrooms, Sleeps 4. Come enjoy our hidden retreat in upscale Cudjoe Gardens. This home is conveniently located only blocks away from Cudjoe Gardens Marina. This single level home is situated on a crystal clear flow through deep water canal. The home features an in ground private ...

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Property Type

Cudjoe Key House

"Perfect Keys Home"

We absolutely loved this home! We've been traveling to the Keys for 15 years and this is one of our favorites. A quiet neighborhood which is fantastic. Fred is excellent with communication.

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3 BR | 3 BA | Sleeps 6 | Quick View

$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool

About this property

Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' ...

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Property Type

Cudjoe Key House

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3 BR | 2 BA | Sleeps 9 | Quick View

$517

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

***We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning, disinfecting, and preparing this home for your arrival. We are following the protocols laid out by the CDC and using the EPA-approved disinfectants for Hard (non-porous) Surfaces, Soft ...

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Property Type

Cudjoe Key House

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2 BR | 3 BA | Sleeps 6 | Quick View

2

Distance to beach: 15 miles to Bahia Honda

$434

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on ...

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Property Type

Cudjoe Key House

"Nice Condo"

Well kept clean condo and good host. The host has a nice binder with information and local things to do with mile markers. I would have liked to have the list emailed to me before we came to plan more ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

$155

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get together. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood floors throughout. 3 large ...

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Property Type

Cudjoe Key House

"Wonderful relaxing vacation home"

We recently stayed at the Sunset Bay home and couldn’t have been happier with the rental. Never having rented a home in the Keys I wasn’t sure what to expect but the Action Keys realty team was efficient ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Paradise Palms! This amazing 3 bedroom home on Cudjoe Key is perfect for your next Florida Keys vacation! Tropical landscaping surrounds an inground pool that overlooks a beautiful canal...everything you could want and more! There is also large concrete dock for your boat, quick easy ocean ...

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Property Type

Cudjoe Key House

"Excellent location & Super clean Home"

My family and I stayed for the month of June 2022 and this was the first time we had visited Cudjoe Key. The house was beautiful and VERY clean. The kitchen was well equipped with everything you needed ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$175

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to your ideal vacation getaway in the heart of the Florida Keys! Located in the serene Cudjoe Key, this charming home offers luxurious amenities and a perfect blend of comfort and style. Imagine waking up in a cozy, beautifully decorated home and enjoying your coffee on a private deck surrounded ...

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Property Type

Cudjoe Key House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

Private Beach, ocean front home with pool on Cudjoe Key.Home includes;- Master bedroom suite with 32' flat screen TV, full bathroom including tub and shower for 2, sliders open to private Master Suite deck with ocean view and private beach.- 2 additional bedrooms with Jack-n-Jill bath- ...

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Property Type

Cudjoe Key House

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3 BR | 2 BA | Sleeps 8 | Quick View

2

Distance to beach: 10 miles to Bahia Honda, Key West

$192

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Wonderful, pet-friendly and beautifully decorated 3/2 home on the water that's perfect for a vacation or simply relaxation. It's located on beautiful Cudjoe Gardens with direct ocean access. There's a marina within walking or rowing distance. Check out the nearby Marvin Key video.Summary: • ...

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Property Type

Cudjoe Key House

"Wonderful"

My husband and myself along with another couple rented this property for 28 days in September 2022. The home is clean, very comfortable and nice. There is a canal at the house which we used to dock 2 boats ...

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4 BR | 3.5 BA | Sleeps 8 | Quick View

$344

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Large recently renovated family home with 4 bedrooms/ 3.5 bathrooms and brand new pool, 20 miles to Key West. House is located on a canal with new concrete dock, minutes to open water. Canal connected to property has open water . Paddle boards, bikes, kayaks and BBQ grill provided. Plenty of outdoor ...

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Property Type

Cudjoe Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$140

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

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 style with lovely accents ...

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Property Type

Cudjoe Key House

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3 BR | 3 BA | Sleeps 6 | Quick View

$200

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Keys. Enjoy boating, fishing or kayaking right from your back door.After ...

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Property Type

Cudjoe Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$89

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Unit #179 - At the “Tree Top Paradise” we have spared no expense to make sure your vacation is not just a vacation but an experience of your life with a peak a boo view of the canal. This home is a fantastic 2 bedrooms (Queen beds) and a sleeper sofa and 2 baths. You have a large lovely screened ...

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Property Type

Cudjoe Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$171

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Come stay at this heavenly oasis. Pull up to a fully fenced 2 bedroom, 2 bathroom Florida Keys home. The front parking area provides parking for you AND your guests. In addition, there is plenty of space to park your water toys on the 60’ of dockage.The home offers beautfiul, vaulted wood ceilings ...

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Property Type

Cudjoe Key House

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3 BR | 3 BA | Sleeps 6 | Quick View

$392

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops.The ...

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Property Type

Cudjoe Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

$239

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Let this Cudjoe Gardens home be the location of your next getaway! Situated on a beautiful, clear deep canal with ample space for your boat, you will enjoy quick access to some of the best fishing, diving and snorkeling in the Florida Keys.This three bedroom home is unique, with two master bedrooms ...

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Property Type

Cudjoe Key House

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4 BR | 3 BA | Sleeps 8 | Quick View

$393

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Looking for a home away from home? Via Villa is the place! This vacation home is located in Cudjoe Gardens on Cudjoe Key, only 20 miles from Key West. Situated on a corner canal, there is ample dockage for large boats, water and electric on the dock, as well as a waterside fish cleaning table. Via Villa ...

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Property Type

Cudjoe Key Villa

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3 BR | 2 BA | Sleeps 6 | Quick View

$179

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

A clean, wide canal with immediate access to Kemp Channel makes this home a terrific choice for boaters, fisherman and divers alike!Situated on Wahoo Lane, Cudjoe, this comfortable 3-bedroom 2 bath stilt home provides, the outdoor island lifestyle; upstairs 2 wide open decks on either side of a screened ...

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Property Type

Cudjoe Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

$275

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

We would like to invite you to stay at our peaceful keys getaway. Enjoy the spacious porch overlooking the pool and canal, this is great for my wife and I to watch our kids while they are swimming and fishing off the sea wall. As you can tell by the pictures you can catch hugh snapper right off the sea ...

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Property Type

Cudjoe Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

1

$259

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends ...

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Property Type

Cudjoe Key House

"Island getaway"

Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$147

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

A comfortable well priced home away from home. This charming 2-bedroom, 2-bathroom cottage offers a spacious, living/dining area with a fully stocked kitchen only steps away from the shaded patio with a water view and firepit.Experience the coastal charm and serenity of waterfront living while being ...

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Property Type

Cudjoe Key Cottage

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2 BR | 2 BA | Sleeps 4 | Quick View

$140

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

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 screen TV. Double sliding doors to ...

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Property Type

Cudjoe Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$276

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This home is situated on a beautiful canal in the prestigious Cudjoe Gardens. It is impressive from the moment you pull in the driveway! There is a tropical grand entryway leading into the spacious and beautifully furnished living room. From there, continue through the sliding glass doors on to the screened ...

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Property Type

Cudjoe Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$156

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This super cozy, comfortable 2-bedroom, 2-bath vacation rental is located in the heart of Cudjoe Key, just minutes from the open ocean. Perfect for fishing, snorkeling, and diving enthusiasts, the home boasts easy access to some of the best spots in the Florida Keys.Relax and unwind in style after ...

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Property Type

Cudjoe Key Bungalow

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Cudjoe Key Vacation Rentals

Cudjoe Key Weather

 | 

7524°  6518°
JANUARY
Ocean 7222°
7624°  6619°
FEBRUARY
Ocean 7222°
7926°  6921°
MARCH
Ocean 7423°
8127°  7222°
APRIL
Ocean 7826°
8529°  7624°
MAY
Ocean 8127°
8831°  7926°
JUNE
Ocean 8329°
8932°  7926°
JULY
Ocean 8530°
8932°  7926°
AUGUST
Ocean 8730°
8831°  7826°
SEPTEMBER
Ocean 8530°
8529°  7624°
OCTOBER
Ocean 8328°
8127°  7222°
NOVEMBER
Ocean 7926°
7725°  6719°
DECEMBER
Ocean 7524°

FAQ

How many vacation rentals are there in/around Cudjoe Key?

There are 35 Cudjoe Key vacation rentals available on FloridaRentals.com. From house rentals to cottage rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Cudjoe Key?

There are vacation rentals available in Cudjoe Key for as low as $89 per night with an average price per night of $272.

Can I find a vacation rental in Cudjoe Key?

Yes, you can find vacation rentals in Cudjoe Key close to Marvin Key, Angelic Moon Day Spa, and Tackle Buster Charters. Don't forget to stop in to Cudjoe Bay.

Do any vacation rentals in Cudjoe Key have a pool?

Yes, there are 13 vacation rentals with a pool in Cudjoe Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Cudjoe Key vacation rentals on the ocean?

There are 12 oceanfront rentals in Cudjoe Key available on FloridaRentals.com. Use our filters to search and book yours today!