Cudjoe Key Vacation Rentals with Boat Dock

(23 rentals)
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Cudjoe Key House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$283

avg/night

$283
avg per night
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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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Property Type

Cudjoe Key House

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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Cudjoe Key House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
5 reviews

$411

avg/night

$411
avg per night
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Key Amenities

  • Air conditioning
  • 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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Property Type

Cudjoe Key House

Featured review

"Vacation 2024/2025"

Southern Sunset is an excellent place to stay! The hosts are very accommodating and were great to chat with and helped make our stay even better. The property is clean and well kept and has a fabulous outdoor ...

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Cudjoe Key House
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
2 reviews

$726

avg/night

$726
avg per night
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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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Property Type

Cudjoe Key House

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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Cudjoe Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 17 miles to Bahia Honda

$376

avg/night

$376
avg per night
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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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Property Type

Cudjoe Key House

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Cudjoe Key House
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms

$658

avg/night

$658
avg per night
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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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Property Type

Cudjoe Key House

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Cudjoe Key House
2 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 3 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda

$429

avg/night

$429
avg per night
View Details

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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Property Type

Cudjoe Key House

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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Cudjoe Key House
2 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 3 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda

$450

avg/night

$450
avg per night
View Details

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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Property Type

Cudjoe Key House

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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Cudjoe Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$550

avg/night

$550
avg per night
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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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Property Type

Cudjoe Key House

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Cudjoe Key House
3 BR | 2 BA | Sleeps 9 | Quick View
Sleeps 9, 3 bedrooms, 2 bathrooms

$517

avg/night

$517
avg per night
View Details

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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Property Type

Cudjoe Key House

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Cudjoe Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$396

avg/night

$396
avg per night
View Details

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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Property Type

Cudjoe Key House

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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$241

avg/night

$241
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

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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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$284

avg/night

$284
avg per night
View Details

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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Property Type

Cudjoe Key House

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Cudjoe Key Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$157

avg/night

$157
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

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 Cottage
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$148

avg/night

$148
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

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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Cudjoe Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$201

avg/night

$201
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

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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Cudjoe Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$141

avg/night

$141
avg per night
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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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Property Type

Cudjoe Key House

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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$288

avg/night

$288
avg per night
View Details

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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Property Type

Cudjoe Key House

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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Cudjoe Key Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$393

avg/night

$393
avg per night
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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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Property Type

Cudjoe Key Villa

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Cudjoe Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

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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Property Type

Cudjoe Key House

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Cudjoe Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$172

avg/night

$172
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

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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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

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

Featured review

"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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Cudjoe Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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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Property Type

Cudjoe Key House

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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$261

avg/night

$261
avg per night
View Details

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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Property Type

Cudjoe Key House

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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Cudjoe Key Vacation Rentals