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Vacation Rentals & Apartments in Cudjoe Key

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115 apartments

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$184

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$197

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$168

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$122

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$178

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$475

Hawkins Heaven

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$141

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$94

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$113

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

Quiet Waters

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$122

Paradise Bay

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$125

Tranquility in Paradise - Cudjoe

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$219

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 27 minutes

Price per night from

$172

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$118

TROPICAL TREASURES - Beautiful Canal Front Home On Cudjoe Key With Quick Open Wa

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$183

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$156

Sunny Lei

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$150

BLUE DOLPHIN - Waterfront Home, Dock Your Boat, Community Pool/Hot Tub, Tennis C

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$179

Pelican Perch

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

Great rentals within 20 miles that match your search

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 16 minutes

Price per night from

$161

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$103

Manatee Bay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$118

Margarita Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$153

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$242

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$243

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$177

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$145

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$516

Bahia Azul

Ramrod Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$258

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$765

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 32 minutes

Price per night from

$172

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$172

Sun Kissed

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$121

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$4,012

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$119

Viewing 38 of 115
rentals in Cudjoe Key

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About Cudjoe Key

Looking for a relaxed break? Look no further than Cudjoe Key in Florida. With property rentals lining the long strip of beach, you'll never be far away from white sands and turquoise seas. Sound like your idea of heaven? You can book property rentals in Cudjoe Key with FlipKey today.

About Cudjoe Key

With a tiny population of just over 1600 residents, Cudjoe Key is the ideal getaway if you're looking for a relaxing vacation.

Originally called Littleton Island, this quiet resort is located on an island in Florida Keys. It's perfect for those wishing to become closer to nature, with the intention to get away from the hustle and bustle of everyday life! Here, you can sit on the beach and expect to see tropical sunsets at dusk or have a splash in the ocean.

Many use Cudjoe Key as a stop off to travel to other nearby destinations, therefore this resort is a perfect weekend resort. In just over 73 miles, you will reach Key Largo and, in just over two hours, you will arrive in the more commercialized resort of Miami, where you can experience a more active atmosphere with a wide array of activities and entertainment.

What to do

Cudjoe Key offers a wide range of activities, however may revolve around watersports and activities due to the wide stretch of beach and fantastic waves. Snorkeling and diving are perhaps the most popular with tourists, especially those who are looking for a taste of adventure on their trip.

Alternatively, if you're looking for more challenging activities, why not try your hand at kayaking and canoeing? You’ll find yourself traveling down water channels surrounding nearby islands – ideal for both beginners and the more advanced.

Those who aren't into extreme sports may prefer chilled out boat trips which can be rented for private use, or you may decide to join a fishing trip around the island and pull in your own catch! Most fishing trips contain guides so you have all the information you need. 

Top Cudjoe Key travel tips

The weather in Cudjoe Key stays regular all year round and during the summer months of July and August, temperatures average at around 28 degrees Celsius, while during the winter months may drop to only 24 degrees Celsius. This makes Cudjoe Key a great destination for all year round.

Many tourists hire their own vehicle when traveling to Cudjoe Key because most activity takes place outside of the resort. Cudjoe Key has its own restaurants and small individual shops, but sorting your own transport would be an essential aspect of your visit to get around.

If you're looking for a relaxed vacation, away from the bustle of normal life, Cudjoe Key is a great choice. With larger resorts just a car drive away, you'll be away from the commercial life, but close enough to experience it should you decide. Book your Cudjoe Key vacation rental with FlipKey today!

Top Destination reviews

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort
Perfect

Very clean, comfortable, and we'll equiped. The view from the canal out over the open water was awesome. The dock was the perfect spot for our sailboat and gave us easy access to our daily sailing adventures. The owner was very informative and friendly and genuinely interested in us having a good experience.see more
Fandango
Awesome Keys vacation!!!

Thank you Kristen and Sharon!!! We had a fantastic vacation! The house was clean and comfortable!!! Anytime we needed anything, management responded promptly!! The kayaks were terrific, the hot tub suprisingly useful, the pool very small but our kids still had a great time!!! One thing for future renters, the screened room would only be able to be slept in during cooler months! It's a great room but very hot! Location was perfect to Key West !!! We'd stay again our next visit! Thank you so much!!see more
Family Retreat-Ocean front home with private pool
What an awesome way, to celebrate my birthday!

This property was very clean, spacious and perfect for our large party. Every morning you would find me on the lanai, enjoying the Cudjoe Bay view, with my computer on my lap and a cup of coffee at my side. The bedrooms were all comfortable and the kitchen had plenty of room for those who enjoyed cooking! Tom the maintenance/pool man was a wealth of information! He answered all our questions and offered lots of suggestions as to where to go or what to do to. If I had to say anything negative about this place it would be that they haven't yet figured out how to make time stand still. Shannon can you work on that?? :-) Everyone in our large party agreed this was the perfect place for our gathering and they are all willing to do it again...see more
Tropical Paradise Oceanfront Home with Pool
Tropical Paradise was truly a paradise.

Six of us stayed in the Tropical Paradise on Cudjoe Key and had a great time. The house was fully equipped with all the things you need for living, all we had to do was buy groceries. There were a couple of things I would like to see added to the home, the main thing being a ramp for someone in a wheel chair or that has problems with stairs. The other is that the maintenance be done when a problem is addressed. Overall our stay was great, we had a couple of little issues. The latch on the gate going off the patio was broken but they fixed that a few days after we got there, the hot water in the hall bathroom shower didn't work and it wasn't fixed while we were there, and we had a light on the porch that didn't work correctly and it wasn't fixed while we were there either. The pool and hot tub were wonderful, the fishing was pretty good and the iguana family was very friendly, after they used to us they would come right up next to us to get feed. One even climbed up my husband's leg to eat grapes out of his hand. It was also nice that the owner provided a list of the best places to eat and things to do. We had a very relaxing and stress free week at this home and if we ever go back to vacation again in the keys we will book this home if it is available.see more
Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)
Sunset was spectacular as advertised

The two person kayak was an added bonus that we enjoyed throughout our stay. Whenever there was any problem (accident in Key Largo knocked out internet, Tropical Storm Eta arrived requiring shutters), the owners were quick to respond and take whatever action they could. They were in touch with us whenever we needed them.see more

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