Luxury Vacation Rentals in Cudjoe Key

(22 rentals)
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6 BR | 4 BA | Sleeps 12 | Quick View

$657

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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5 BR | 3 BA | Sleeps 12 | Quick View

2

$643

avg/night

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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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5 BR | 3 BA | Sleeps 12 | Quick View

2

$610

avg/night

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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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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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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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3 BR | 3 BA | Sleeps 6 | Quick View

$500

avg/night

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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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2 BR | 3 BA | Sleeps 6 | Quick View

4

Distance to beach: 15 miles to Bahia Honda

$497

avg/night

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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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2 BR | 3 BA | Sleeps 6 | Quick View

2

Distance to beach: 15 miles to Bahia Honda

$452

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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4 BR | 3.5 BA | Sleeps 8 | Quick View

$450

avg/night

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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. Perfect for boats 25ft or smaller. Paddle boards, bikes, kayaks and BBQ grill provided. Plenty of outdoor parking, ...

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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

$430

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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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

"Boat Rental From Perfect Hosts"

Wanted to drop a quick note of appreciation to John and Martha. My wife and I originally intended to rent Southern Sunset for the month of March. We have a large extended family and the property was perfect ...

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3 BR | 3 BA | Sleeps 6 | Quick View

$390

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 8 | Quick View

Distance to beach: 17 miles to Bahia Honda

$376

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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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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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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2 BR | 2 BA | Sleeps 4 | Quick View

$272

avg/night

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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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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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3 BR | 2 BA | Sleeps 6 | Quick View

1

$256

avg/night

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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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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 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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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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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 15 miles to Bahia Honda State Park

$215

avg/night

View Details

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 ALLOWEDRecently reduced our prices!! ...

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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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Cudjoe Key Vacation Rentals