Vacation Rentals & Apartments in Cudjoe Key

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Price per night from

$229

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$791

Catch of the Day!

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$126

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$774

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Price per night from

$574

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

$476

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$149

Pirate's Cove

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$101

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$121

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$574

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$130

Quiet Waters

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$141

Tranquility in Paradise - Cudjoe

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$218

$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

Price per night from

$258

5 O'Clock Somewhere

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$124

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 2 hours 48 minutes

Price per night from

$602

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

$224

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$434

Price per night from

$179

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$161

Price per night from

$179

Price per night from

$180

Great rentals within 20 miles that match your search

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$144

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Big Torch Retreat

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$141

Pirates Pointe

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$158

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

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$114

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

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 18 minutes

Price per night from

$688

Conch Out

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$173

Hideaway Bay

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$128

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

Price per night from

$230

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$308

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$128

Viewing 38 of 129
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

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
Ocean View Estate with Private Pool 15 minutes from Key West
Absolutely Perfect for Our Family of 11

We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we needed something, we could find it easily, or we called Cynthia---her help and knowledge is priceless! Kris stopped in twice to check on us, and we found him delightful. He knows so much history about the area! There is a large pool and a large play area with anything and everything you can imagine to play with, Since we had very young children with us, we were very happy with the lack of ocean access, as well as the locking gates to the pool area and the outside stairs. When we come back to the Keys, we will definitely stay at the White Ibis Inn! … see more

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