Skip to content
Home » Vacation Rentals » Cudjoe Key

Cudjoe Key Vacation Rentals, Cottages and Beach House Rentals.

Large selection of Rentals, book your Cudjoe Key Vacation Rental Home Here and Save!

Many rental properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.

Rentals by Owner in Cudjoe Key Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of Short Term Rentals to choose from, we now have the selection and value to offer our visitors searching for places to rent in Cudjoe Key Florida.

Select from the following Rental Properties:

Quaint cottage, pool, dockage just minutes to Key West!

Cudjoe Key Cottage Star 4.5 Star Review

Cottage #5 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. One of our most spacious cottages; it offers a full kitchen, screened patio, two queen bedrooms. This cottages is only steps away from our pool. The dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you c.......read more

2 Bedrooms - Sleeps 4
Cottage in Cudjoe Key



Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cudjoe Key Cottage Star 4.3 Star Review

Cottage #1 - Quaint, clean, comfortable cottage just 20 miles from Key West. Located on the oceanfront. Cottage offers a full kitchen, screened patio, a single bedroom with a queen bed. A few steps in either direction bring you to sparkling water. This cottages is situated on the waterfront, but only steps away from our pool. The dock, seawalls are.......read more

1 Bedrooms - Sleeps 2
Cottage in Cudjoe Key



Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key Cottage Star 4.4 Star Review

Cottage #3 - Quaint, clean, comfortable cottage just 20 miles from Key West. Located on the oceanfront. Cottage offers a full kitchen, screened patio, a single bedroom with a queen bed. This cottage is only steps away from our pool. The dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to t.......read more

1 Bedrooms - Sleeps 2
Cottage in Cudjoe Key



Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Cudjoe Key Vacation Rental Star 4.7 Star Review

RECENTLY remodeled with beautiful Keys colors. This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, direct access to the Atlantic and the Gulf via Kemp channel, 35\' concrete dock/seawall with a fish cleaning station. Beautiful views of the open water from the living room, dining .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key



Remodeled, Waterfront Stilt home

Cudjoe Key Vacation Rental Star 4.5 Star Review

Time to relax at this beautifully remodeled 2 bedroom, 2 bath waterfront vacation home. This Key West style stilt home features a 35\' concrete seawall for docking your boat, equipped with dockposts, cleats, a fish cleaning table, fresh water rinse down and fresh water outdoor shower.

The living room is nicely decorated and has a queen sle.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key



VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View

Cudjoe Key Vacation Rental Star 4.9 Star Review

Canal Front 35 Seawall - Simply elegant describes this 2 Bedroom with 2 full Bathrooms, canal front stilt home! This home features a 35 concrete seawall with access to the Gulf & Ocean! Ocean views from the dock and porch! Dock amenities include dock posts, cleats and fish cleaning table. Covered porch with comfortable lounging furniture overlookin.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key



Ocean view, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w/ shower!

cudjoe key Vacation Rental Star 5.0 Star Review



Located in a great neighborhood at 1032 Spanish Main, this home is perfect for your next vacation. We are at the end of a dead end street so it is very private. This very clean and neat 3 bedroom 2 bath home has a new granite kitchen that has just been enlarged, bar top with 3 bar stools, a table for seating as well, dishwasher, large r.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in cudjoe key



Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key Cottage Star 4.5 Star Review

Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. The pool, dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida.......read more

2 Bedrooms - Sleeps 4
Cottage in Cudjoe Key



Sparkling Clean & New Turn Key 1Bd/1Ba

Cudjoe Key Vacation Rental Star 4.8 Star Review

This beautifully decorated vacation home is located on a WIDE Y-SHAPED CANAL that overlooks a common ground with over 100\' plus of expansive water views!  Features many upgrades throughout including custom kitchen and bath, central air conditioning.  Located on a gorgeous landscaped lot, front yard offers partial open water views.  Great for bo.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Cudjoe Key



Key Lime Cottage in Cudjoe Key

Cudjoe Key Cottage Star 4.5 Star Review

Lot 144 - Beautiful 2 Bedroom/2 Bath Cottage in Cudjoe Key available for daily, monthly and seasonal rentals. Home has been decorated with new furnishings - May, 2017. Brand new upgraded split AC SYSTEM (3zone) 2017. Newer Kitchen and Baths.Beautiful private backyard area with table seating for six and gas grill. Home includes queen bed, trundle b.......read more

2 Bedrooms - Sleeps 5
Cottage in Cudjoe Key



Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key Cottage Star 4.5 Star Review

Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. This cottages is only steps away from our pool. The pool, dock and seawall are all available to our guests. A coin laundry is also av.......read more

2 Bedrooms - Sleeps 4
Cottage in Cudjoe Key



Yellow Vacation Home. Private heated pool. Water view.

Cudjoe Key Vacation Rental Star 4.9 Star Review

This vacation home is nestled far off of US 1. Kayaks included in the rental. Rent one or both of our other properties that are all on 3 acres of land for a great family vacation. Listing #\'s are 3586076 and 7105866. We also rent pontoon and center console boats. Private heated pool with seats inside of the pool to enjoy the view out to Cudjoe Bay.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key



White Vacation Home. Private heated pool, and great view of the Atlantic Ocean.

Cudjoe Key Vacation Rental Star 4.9 Star Review

Kayaks are included with the rental. Property has a small floating dock for your boat. We have 2 other homes right next to this home, if you are looking for a large family vacation. Homeaway.com listing #\'s are 7105866 and 7154549. We also rent pontoon and center console boats. Home has a large flat screen TV with over 330 free current movies, and.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Cudjoe Key



Blue Vacation Home with private heated pool.

Cudjoe Key Vacation Rental Star 5.0 Star Review

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 nearby, at no extra charge. We also rent pon.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Cudjoe Key



Private pool, spectacular views & dock

Cudjoe Key Vacation Rental Star 4.8 Star Review


Fandango was designed as the ultimate vacation experience. This house includes all the elements you need for an amazing vacation. Outside the house there are kayaks for adventures, a swimming pool, private beach with loungers and Adirondack chairs for relaxation, a floating dock for fishing and docking a boat. The dock can accommodate up to.......read more

5 Bedrooms - Sleeps 12
Vacation Rental Home in Cudjoe Key



Scroll To Top