Language and Currency

Select your language and currency preferences for the site. Please note that all transactions will be processed in USD

Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Cudjoe Key Rentals

1 - 42 of 258 rentals
  PrevNext  
Sat 26 May Sun 27 May Mon 28 May Tue 29 May Wed 30 May Thu 31 May Fri 1 Jun Sat 2 Jun Sun 3 Jun Mon 4 Jun Tue 5 Jun Wed 6 Jun Thu 7 Jun Fri 8 Jun Sat 9 Jun Sun 10 Jun Mon 11 Jun
Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
- - 312 - - - - - - - 330 349 358 330 - - -
Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
- - 187 192 191 189 167 - - - - - - 161 - - -
Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
- - 167 173 162 - - - 171 158 151 - - - - - -
Bliss - Key West, FL Vacation Rental

Bliss

Key West, FL
2 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
 Modern Rendezvous  - Key West, FL Vacation Rental

Modern Rendezvous

Key West, FL
2 Bed 2 Bath Sleeps 4
1035 1000 1041 1018 1014 1005 1043 1032 1061 939 950 953 975 1050 1034 998 1003
Tropical Breeze - Key West, FL Vacation Rental

Tropical Breeze

Key West, FL
0 Bed 1 Bath Sleeps 2
- - 133 - - 126 - - 143 127 130 123 - - - 128 137
Live Laugh Love - Marathon, FL Vacation Rental

Live Laugh Love

Marathon, FL
2 Bed 2 Bath Sleeps 4
145 150 157 156 157 156 159 168 167 167 166 166 167 159 168 177 178
Truman @ Duval - One Bedroom - Key West, FL Vacation Rental
183 175 182 177 176 174 182 180 186 159 161 162 167 184 180 169 170
Gecko Grotto - Key West, FL Vacation Rental

Gecko Grotto

Key West, FL
0 Bed 1 Bath Sleeps 2
- - 126 - - - - - 136 115 - - - - - - -
Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
- - 167 173 172 161 - - - - 144 - - - - - -
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 131 138 129 - - 136 114 - - - - - 125 133
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - - - 212 - - - - - - - 196 -
Passover Cottage - Key West, FL Vacation Rental

Passover Cottage

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - 400 387 - - - 486 444 426 - - - - - -
Shark Key Chateau - Key West, FL Vacation Rental

Shark Key Chateau

Key West, FL
5 Bed 4.5 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Paris Mango @ Key Cove - Key West, FL Vacation Rental

Paris Mango @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
261 255 254 241 238 247 288 286 301 276 278 279 283 289 286 284 284
Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
0 Bed 1 Bath Sleeps 2
- - 135 139 138 129 - - 143 120 - - - - - - -
A Key Escape - Key West, FL Vacation Rental

A Key Escape

Key West, FL
3 Bed 2.5 Bath Sleeps 8
- - - - - - - - 497 - - - - - - 440 -
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - 133 134 - - 142 166 166 166 166 158 - - - 151
Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
- 472 489 487 488 484 427 - - - - - - - - - -
Caribbean Dreams - Key West, FL Vacation Rental

Caribbean Dreams

Key West, FL
0 Bed 1 Bath Sleeps 2
- 159 - - - - - - 139 124 126 126 123 - - 125 133
West Indies - Key West, FL Vacation Rental

West Indies

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - 126 - - 136 121 123 117 - - - - -
Shipyard Perch  - Key West, FL Vacation Rental

Shipyard Perch

Key West, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - 199 242 - - - - - - - 189
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - 192 180 182 182 186 163 - - -
Sunset Place - Key West, FL Vacation Rental

Sunset Place

Key West, FL
3 Bed 2 Bath Sleeps 6
- 171 178 174 173 171 178 176 181 160 162 163 166 179 176 170 171
Writer's King Room - Key West, FL Vacation Rental

Writer's King Room

Key West, FL
0 Bed 1 Bath Sleeps 2
- - 133 - - - - - 137 - - - - - - 122 130
Tsalta - Key West, FL Vacation Rental

Tsalta

Key West, FL
3 Bed 3 Bath Sleeps 8
- 271 253 227 217 236 263 259 287 241 245 246 254 266 260 245 246
Aqua Pearl Crest  - Key West, FL Vacation Rental

Aqua Pearl Crest

Key West, FL
3 Bed 3.5 Bath Sleeps 8
179 179 179 166 162 177 215 215 215 200 205 205 214 215 215 200 200
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - 174 - - - - 296 323 327 306 - - - 331 364
Truman @ Duval - Studio - Key West, FL Vacation Rental

Truman @ Duval - Studio

Key West, FL
0 Bed 1 Bath Sleeps 2
183 175 182 177 176 174 182 180 186 159 161 162 167 184 180 169 170
Banana Breeze @ Key Cove - Key West, FL Vacation Rental

Banana Breeze @ Key Cove

Key West, FL
4 Bed 3.5 Bath Sleeps 10
257 251 250 237 234 231 - - - - - - - - - - -
Commodore's Cove - Key West, FL Vacation Rental

Commodore's Cove

Key West, FL
4 Bed 4 Bath Sleeps 12
- - - - - 454 - - - 426 435 - - - - - -
Nautical Wheeler  - Key West, FL Vacation Rental

Nautical Wheeler

Key West, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Whitehead Manor - Key West, FL Vacation Rental

Whitehead Manor

Key West, FL
5 Bed 2 Bath Sleeps 9
- - - - - - - - 155 149 149 149 149 164 164 151 153
Toon Hall - Tropical Village - Key West, FL Vacation Rental
- - 376 362 353 358 - - - - - - - - - - -
Helen's Hideaway - Key West, FL Vacation Rental

Helen's Hideaway

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - 394 - - - -
Anchors Aweigh Retreat - Marathon, FL Vacation Rental

Anchors Aweigh Retreat

Marathon, FL
2 Bed 2 Bath Sleeps 6 (5 Adults Max)
145 150 157 156 149 - - - - - 158 166 167 135 - - -
Waterfall 4 - Key West, FL Vacation Rental

Waterfall 4

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - 97 - - - - -
Amelia House - Key West, FL Vacation Rental

Amelia House

Key West, FL
3 Bed 2 Bath Sleeps 8
- - - - 389 431 390 - - - - - - - - - -
Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
257 251 250 237 234 243 284 281 296 272 261 - - - - - -
Audubon House - Key West, FL Vacation Rental

Audubon House

Key West, FL
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - 153 - - - - - -
Secret Garden - Key West, FL Vacation Rental

Secret Garden

Key West, FL
2 Bed 1 Bath Sleeps 4
221 211 196 174 169 175 - - - - - - - - - - -
Page 1 of 7

About Cudjoe Key

If the sun, sand, and water of the Florida Keys is calling your name, consider spending your next vacation on Cudjoe Key, FL, where you'll find all the water sports the Keys are known for in a spot that's a bit less traveled, giving you a chance to wrap yourself in Florida's beautiful natural surroundings and reconnect with your family, friends and yourself. What better way to revel in the soothing benefits of the Keys than to stay in one of our cozy vacation rentals?

Where is Cudjoe Key, FL?

This small key is located between Sugarloaf Key and Big Pine Key in the lower reaches of Florida's famous island chain. To get here, simply follow US Highway 1 from Miami for 140 miles, or make the 20-mile drive from diverse and exciting Key West if you're coming the other way.

This island is also home to the Cudjoe Key Air Force Station, where you will see the notorious Fat Albert. A long white blimp, Fat Albert is used by the US Federal government to patrol boat traffic and aircraft using radar devices.

Things to Do on Cudjoe Key, FL

Get out on the water with a charter excursion or rent a boat and captain your own ship. Drop your line starboard and catch a tarpon or shark, or get beneath the surface of the sparkling waters and do some snorkeling or diving. Paddle your way through the channels in a kayak, or rent a bike and peddle peacefully through a tropical paradise.

Looking for relaxation? Indulge yourself at Angelic Moon Holistic Day Spa. The only green-focused day spa in the Keys, Angelic Moon uses natural, organic, fair-trade ingredients in all their treatments, with an eye on a whole-person approach to bringing you to a state of blissful relaxation and rejuvenation. 

Take an easy, breezy day trip to Summerland Key, four miles away, for an eco tour or to check out the reefs. No matter how you fill your days on Cudjoe Key, you'll be happy to return to your own private vacation rental to savor a freshly cooked meal and enjoy the comforts of home.

Photo Credit: keyslibraries via Flickr

  • Searching ...
  • 42 of 258
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here