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Cudjoe Key Vacation Rentals with Boat Dock

(18 rentals)
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

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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$308
avg per night
Cudjoe Key House
Sleeps 12, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$807
avg per night
Cudjoe Key House
Sleeps 10, 4 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"The Perfect Vacation Home"

The location of Southern Sunset couldn't be more perfect. Only 25 minutes to Key West, 5 min to a great little grocery store called Murrays (and maybe 15 min to Winn Dixie), a short drive to Capt Hooks...

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$442
avg per night
Cudjoe Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 17 miles to Bahia Honda

Key Amenities

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

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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Featured review

"Outstanding home"

House is very spacious and open. Open water views and unbelievable deck for sunsets. Neighbors very welcoming and friendly. Already booked for next year

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$330
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$460
avg per night

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Cudjoe Key House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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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$550
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$454
avg per night
Cudjoe Key House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

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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$500
avg per night
Cudjoe Key House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

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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$658
avg per night
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

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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$150
avg per night
Cudjoe Key Villa
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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$393
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 10 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"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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$330
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to El Paraiso, a true Cudjoe Key gem at an affordable price. This three bedroom, three bath home is nicely updated throughout! Located on Lafitte Drive, right behind the famous Square Grouper restaurant and only 20 minutes from Key West. Don’t forget to bring your boat, there is plenty of...

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$227
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

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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Featured review

"FABULOUS!"

This was the best vacation I have ever had in Florida. The house was beautiful and it was very peaceful sitting out on the canal. Only 20 miles to Key West makes for easy day trips. We went 5 times! The...

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$186
avg per night
New
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Available for the 2026 season! (weekly rentals permitted) Affordable piece of paradise! Escape the cold and come enjoy this Venture Out home with open concept, bright and airy rooms, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you’ll be amazed. This fully furnished home...

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$214
avg per night
Cudjoe Key House
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

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

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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Featured review

"Fantastic view"

We really enjoyed the large house. The easy to launch kayak area was very convientant. Location was great - 25 minutes to Key West. The sunsets were breathtaking. House was well equipped with every you...

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$283
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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$433
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning

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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Featured review

"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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$277
avg per night
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