Cudjoe Key Vacation Rentals, Cottages and Beach House Rentals.

Cottage in Cudjoe Key

Wanna go on vacation but feel Cozy as if your home? ? We got the place for you!
2 bedroom,1 bathroom with living room,dining room and kitchenette in a secure gated community of Venture Out.Fully furnished,Colorful & great island vibe.

This is a Florida lovers Paradise.
This dry lot home can sleep 6. The house is fully furnished with a colorful island vibe. 2
modern bedrooms and 1 full bathroom.
There is a queen bed in the bottom floor bedroom,along with AC & a flat screen.......

4.4 Star Review

Cottage in Cudjoe Key

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 come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Co.......

4.5 Star Review

Cottage in Cudjoe Key

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 the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Cottages to be your .......

4.4 Star Review

Cottage in Cudjoe Key

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 all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm .......

4.3 Star Review

Private Vacation Home in Cudjoe Key

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 room, perfect location to tie up your boat. This is a fully furnished 2 bedroom 2 bath home with spectacular sunrise and sunset views. The master bedro.......

4.7 Star Review

Private Vacation Home in Cudjoe Key

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 overlooking the water. Interior features tile flooring, mounted living room flat screen TV, full line of appliances, washer, dryer, ceiling fans and central A/C.......

4.9 Star Review

Private Vacation Home in cudjoe key

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 refrigerator, microwave, Kuerig coffee maker and a regular one, garbage disposal, all the kitchen amenities you can want. The living room is huge with .......

4.7 Star Review

Private Vacation Home in Cudjoe Key

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 friends. Gather together a group for a game of bocce. Forgot a "good read"? No worries - we have a well-stocked library. There's a playground as well.......

5.0 Star Review

Private Vacation Home in Cudjoe Key

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 a 24' boat. There is tropical foliage including coconut palms and bananas, a screened in porch for dining al fresco and so much more. Inside the ho.......

4.8 Star Review

Condo in Cudjoe Key

VO365
Sirena Key Cottage
​​​​​​​ 35' Seawall
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 bedroom full bed and bathroom with stand up shower. Amenities include central air conditioning, ceiling fans, tile floor.......

3.9 Star Review

Private Vacation Home in Cudjoe Key

Ocean Front 35’ Seawall – Spectacular views from this 2 Bedroom 2 Bathroom ocean front stilt home! This home features a 35’ concrete seawall with easy access to the Gulf & Ocean! Gorgeous Open Water Ocean views from living room, kitchen, dining area, covered porch and dock! Dock amenities include dock posts, cleats and whips. Covered porch with comfortable lounging furniture overlooking a beautiful water view. Interior features tile flooring throughout, TV in living room and master bedroom.......

5.0 Star Review

Private Vacation Home in Cudjoe Key

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 steel appliances with ice maker. Sleeping accommodations include a Queen size bed in the Master Bedroom, a Queen size bed in the Guest Bedroom.

4.5 Star Review

Mobile Home in Cudjoe Key

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 WINDOWS AND DOORS, NEW INTERIOR WALL PANELING, NEW OUTLETS AND SWITCHES, NEW FANS AND LIGHT FIXTURES, NEW FURNISHINGS, NEW FLOORING, NEW CABINETS, NEW QUARTZ.......

4.7 Star Review

Private Vacation Home in Cudjoe Key

 Oceanfront Home, Pool Access/50 Ft Dock Fresh & Fabulous best describes this newest listing . This fantastic Ocean home is in a Island resort community that is one the most unique places in the world. Its stylish 2 Bedrooms & living area will make you stay in Paradise one to remember. Our deep water dock will accommodate most boats. In minutes you can enjoy the Pool resort or you can fish off your dock. Resort 1 time fee $125.......

4.7 Star Review

Private Vacation Home in Cudjoe Key

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 grill and kitchenware to enjoy while watching the sunset. (A fishing license is required. Please purchase one at https://myfwc.com/license/ ).

4.6 Star Review

Cottage in Cudjoe Key

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 site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cud.......

4.2 Star Review

Cottage in Cudjoe Key

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 to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and gre.......

4.2 Star Review

Private Vacation Home in Cudjoe Key

Welcome to Base Camp
YOUR FLORIDA KEYS CANAL FRONT HOME AWAITS...
Relaxation at it's finest! Once you arrive at this gorgeous home, you'll instantly feel vacation mode has begun. Relax on the screened porch and take in the tropical breezes and palm trees swaying in the wind. Take your boat out to enjoy some world class fishing or pull up to one of the famous nearby sandbars or paddle out on kayaks or the double canoe. Relax downstairs and take in the sunshine on the lounge chairs or chill .......

2 Bedrooms - Sleeps 6
Vacation Rental in Cudjoe Key

Private Vacation Home in Cudjoe Key

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 4 persons.

You can add the Honeymoon cottage on it’s own 2 acres, with 1 bedroom with 360 degrees of open water views, one full bathroom and .......

4.7 Star Review

Private Vacation Home in Cudjoe Key

Recently restored 2 bedroom, 2 bath classic Florida home sleeps 6 with original terrazzo floors in prestigious Cudjoe Gardens. Home is beautifully decorated and is open and airy with fabulous gourmet kitchen/dining/den area and separate living room. Master bedroom is spacious and has a King size bed. The guest room has beautiful twin 4-poster beds. Lanai overlooks pristine canal and outdoor dining area. Landscaped yard features coconut palms and other tropical plants, outdoor dining room an.......

5.0 Star Review

Caravan Park/Campsite in Cudjoe Key

Bring your own RV and experience the majestic beauty of the Florida Keys at this beautiful Oceanfront RV Lot! Lot features a 40 foot concrete seawall, concrete pad, heavy duty dock posts, cleats, and swim ladder. Lot comes complete with water, electricity (30-50-110 amp service) & sewer hookup and parking for one vehicle. Make some lasting memories by camping in the Florida Keys today! Venture Out is a 24 hr gated community located only 19 miles from Key West! Amenities include oceanfront .......

5.0 Star Review

Cottage in Cudjoe Key

“The Barnacle” located in Block 8 of Venture Out! One of the communities smaller two (2) Bedroom units packed with large amenities and a full 35’ seawall with an amazing unobstructed view. This home was renovated in 2022/2023 and can comfortably accommodate up to six guests with two queen beds and one full size bed. All new LG appliances, a tankless water heater, ceramic tile, marble tile, new lighting, a redesigned kitchen with granite, keyless entry and new flooring throughout! Living .......

2 Bedrooms - Sleeps 6
Vacation Rental in Cudjoe Key

Private Vacation Home in Cudjoe Key

House B - This lovely 3 bedroom 2 full bath home is located on the Atlantic Ocean. There is always a gentle breeze on the deck facing the ocean with a sunrise view. Comfortably sleeping six guest with dockage available.This property has a sunrise view, grassy yard for grilling. The kids and pets can swim and play all day. Boating, fishing and ocean snorkeling from the property. There also is a pool. All linens and dishes are provided along with washer and dryer........

4.4 Star Review

Private Vacation Home in Cudjoe Key

Beautiful vacation spot on Cudjoe Key perfect for you and your family. This wonderful one bedroom home filled with colorful patterns can turn a boring vacation to an adventurous one. If you stay here you’ll definitely have the perfect tropical vacation in paradise. VO REGISTRATION FEE $125.00 DUE UPON ARRIVAL. Enjoy community activities and full use of the amenities;  Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, Private Convenience Store, Children's Pool, Bath H.......

3.1 Star Review

Private Vacation Home in Cudjoe Key

This tropical vacation home offers two bedrooms, one bathroom and is located in a gated community just 19 miles form Key West. Parking for one vehicle and all amenities are within walking distance from this property! Amenities include: Heated saltwater pool, jacuzzi, saltwater swimming area, tennis, pickleball, basketball and bocce courts, ping pong, pool table, darts, kiddie pool and playground, boat launch, convenient store with fuel dock and much more. Please note this property is not locat.......

4.1 Star Review

Private Vacation Home in Cudjoe Key

A cozy and small mobile home with Marina access and a boat ramp. With almost perfect weather you experience in the Keys you're bound to tan on the back half of this property. With a shared tennis court there's never a dull moment on this Marina. Experiencing an almost perfect mix of a more rustic yet still modern aesthetic you are most definitely going  to feel at home while staying here. Staying here you'll most definitely  have a fun time!  Enjoy community activities and full use of the ame.......

4.6 Star Review

Private Vacation Home in Cudjoe Key

Parrotfish Point

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Located between Sugarloaf Key and Big Pine Key, this upscale, three-bedroom, waterfront house is beautifully furnished, and with its amazing sunset views, a private pool, and a 40-foot dock, it's perfect for your family's next sun-filled getaway! First thing: step into the kitchen to make some refreshments and look out over the Sa.......

5.0 Star Review

Private Vacation Home in Cudjoe Key

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch for your outdoor dining enjoyment. This a very relaxing and beautiful location. There is dining for 12 inside and dining for 12 on the screened in porch. There are several local restaur.......

4.7 Star Review