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Lower Florida Keys Vacation Rentals, Beach Houses & Cottages.

Book Your Lower Florida Keys Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Lower Florida Keys 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 Lower Florida Keys Florida.

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 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Casa Aqua - 16 Acre Spanish Style Open Water Casual Elegance

Cudjoe Key Private vacation home Star 4.8 Star Review

This island oasis called CASA AQUA is a 16 acre Spanish Mediterranean estate on the Atlantic Ocean.

More than all you could want with 5 bedrooms and 3.5 baths in the main house, large pool, hot tub, boat dock, fully equipped kitchen and much more!!
There is a 12 person maximum unless also renting the cottage that sleeps an additional .......read more

5 Bedroom(s)
4 Bath(s) Sleeps 15


Vacation Rental


Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key Cottage Star 4.3 Star Review

Cottage #2 - Charming and serene, clean, comfortable cottage just 20 miles from Key West. Located adjacent to the pool. Cottage offers a full kitchen, screened patio, a single bedroom with a queen bed. This cottage is situated only steps away from our pool. The dock, seawalls are all available to our guests. A coin laundry is also available on sit.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Rental


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

Cudjoe Key Private vacation home 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 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


Casa Del Mar in Venture Out Unit 253

Cudjoe Key Mobile home Star 4.6 Star Review

VO253
Open Water Views 35\' Dockage
Sparkling Clean 2Bd/1Ba Vacation Home!
THIS IS ONE OF THE NICEST UNITS IN ALL OF VENTURE OUT!!! THE HOME HAS BEEN COMPLETELY RENOVATED TOP TO BOTTOM IN MARCH OF 2018 INCLUDING BUT NOT LIMITED TO THE FOLLOWING - NEW ROOF, NEW AC AND DUCT WORK, NEW HOT WATER TANK, NEW SIDING AND SKIRTING, NEW TINTED WINDOW.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Rental


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

Cudjoe Key Private vacation home 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 Bedroom(s)
4 Bath(s) Sleeps 8


Vacation Rental


Cudjoe Bay Access Vacation House In Paradise

Cudjoe Key Private vacation home Star 5.0 Star Review

Welcome to our house in paradise. This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic Ocean on Cudjoe Key and is roughly 22 miles from Key West at Mile Marker 23. Watch the sunrise and sunset from the same southern facing deck overlooking the canal. You can fish in the canal then cook your catch on the provided gr.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6


Vacation Rental


Venture Out Unit 61 Open Water View

Cudjoe Key Private vacation home Star 4.5 Star Review

VO061
Open Water Views From This Stilt Home
Large Covered Patio
Beautifully furnished and decorated 2 bedroom/1 bath stilt home with open water views. This home features a spacious screen porch with views of the Atlantic. Dining room features seating for 6 with designer coral cut glass table and bamboo chairs. Kitchen features stainless.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


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 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Rental


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 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Yellow Vacation Home. Private heated pool. Water view.

Cudjoe Key Private vacation home 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 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


Luxury Home #109-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep

Cudjoe Key Private vacation home Star 5.0 Star Review

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. I also rent units 111 and 107 on VRBO 4441714 and 342851) in case you need more than one home. We are 80 feet the water\'s edge facing Southwest. Lounge in your private hammock or enjoy the gorgeo.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Rental


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

Cudjoe Key Cottage Star 4.3 Star Review

Cottage #13 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. SpaciouQuaint, 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.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Luxury Home #111-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep

Cudjoe Key Private vacation home Star 4.9 Star Review

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. (I also rent units 109 and 107 on VRBO 4441696 and 342851) in case you need more than one home. We are right on the water\'s edge facing Southwest. Lounge in your private hammock or enjoy the gorg.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Rental


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

Cudjoe Key Private vacation home Star 4.7 Star Review

Wonderful, pet-friendly, and beautifully decorated 3/2 home on the water that’s perfect for a vacation or simply relaxation. It’s located on beautiful Cudjoe Gardens Key with direct ocean access with no bridges. There’s a marina within walking or rowing distance. Check out the nearby Marvin Key video.

Summary:
Internet - Includedread more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Rental


NEW LISTING - Cudjoe Key - Canal with Quick Ocean Access

Cudjoe Key Private vacation home

Home is located in a very quiet and nice neighborhood! Home is minutes away from Key West or Big Pine for quick access to great restaurants and shopping! Home sits right on a beautiful, private canal, only 100 yards away from open water! Kemp channel is right in the backyard, so you will have easy access to both the Gulf and Atlantic sides! Marina .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Rental


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 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


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

cudjoe key Private vacation home 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 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Rental


Private pool, spectacular views & dock

Cudjoe Key Private vacation home 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 Bedroom(s)
3 Bath(s) Sleeps 12


Vacation Rental


3/2 Cudjoe Key waterfront single level house.

Cudjoe Key Private vacation home Star 5.0 Star Review



If you are looking for a great place to kick back and enjoy the easy Keys lifestyle, then Blue Heaven is just for you.

This ground-level three-bedroom two bath home is located on the ocean side of Cudjoe Key with a great deep canal and a marina just around the corner. The home features eclectic and colorful decor with a mix of antiq.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Rental


Luxury Home #107-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep

Cudjoe Key Private vacation home Star 4.8 Star Review

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. (I also rent units 109 and 111 on VRBO 4441696 and 4441714 in case you need more than one home.) Our home is third from the waters edge facing Southwest. Lounge in your private hammock or enjoy th.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Rental


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 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Rental


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

Cudjoe Key Cottage Star 4.6 Star Review

Cottage #14 - 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 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Blue Vacation Home with private heated pool.

Cudjoe Key Private vacation home 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 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Rental


Remodeled, Waterfront Stilt home

Cudjoe Key Private vacation home 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 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


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

Cudjoe Key Private vacation home 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 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


Sirena Key Cottage in Venture Out

Cudjoe Key Condo Star 4.5 Star Review

VO365
Sirena Key Cottage

It\'s a wonderful time to enjoy Paradise! Quick ocean side access to gulf and ocean, near Looe Key Reef. Main living room overlooking water with two sliders off open porch to bring the outdoors in. Master suite with queen size bed with full bathroom and lots of closet storage and stack washer/dryer. Guest bedr.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Rental


BIG BLUE waits for you in the sunny Keys

Cudjoe Key Private vacation home Star 4.9 Star Review

Our vacation home in the Lower Keys awaits your arrival! We live here during the winter so our home is available spring - fall. The gated, community of Venture Out has all of the amenities that you could want for a sunny getaway. Lounge by, and swim in the heated pool or salt water canal. Play pool, ping pong, tennis or pickle ball with family and.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Rental


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 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Rental


Sparkling Clean & New Turn Key 1Bd/1Ba

Cudjoe Key Private vacation home 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 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Rental


Sugarloaf Key
Big Pine Key
Little Torch Key
Marathon
Key Colony Beach
Key West
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