Cudjoe Key Vacation Rentals, Cottages and Beach House Rentals.

Cudjoe Key Cottage 4.4 Star Review

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.......read more

3 Bedrooms - Sleeps 6
Cottage in Cudjoe Key

Cudjoe Key Cottage 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

Cudjoe Key Cottage 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

Cudjoe Key Cottage 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

Cudjoe Key Vacation Rental 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 r.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 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

cudjoe key Vacation Rental 4.7 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

Cudjoe Key Vacation Rental 5.0 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 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 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

Cudjoe Key Condo 3.9 Star Review

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.......read more

2 Bedrooms - Sleeps 6
Condo in Cudjoe Key

Cudjoe Key Vacation Rental 5.0 Star Review

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 wi.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 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 Bedrooms - Sleeps 4
Vacation Rental Home in Cudjoe Key

Cudjoe Key Mobile home 4.7 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 WINDOWS.......read more

2 Bedrooms - Sleeps 6
Mobile home in Cudjoe Key

Cudjoe Key Vacation Rental 4.7 Star Review

 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 yo.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 4.6 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 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Cottage 4.2 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 Bedrooms - Sleeps 2
Cottage in Cudjoe Key

Cudjoe Key Cottage 4.2 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 Bedrooms - Sleeps 4
Cottage in Cudjoe Key

Cudjoe Key Vacation Rental

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 o.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 4.7 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 Bedrooms - Sleeps 15
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 5.0 Star Review

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 be.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Caravan Park/Campsite 5.0 Star Review

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 memo.......read more

Studio - Sleeps 6
Caravan Park/Campsite in Cudjoe Key

Cudjoe Key Cottage

“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.......read more

2 Bedrooms - Sleeps 6
Cottage in Cudjoe Key

Cudjoe Key Vacation Rental 4.4 Star Review

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.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 3.1 Star Review

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.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 4.1 Star Review

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 po.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 4.6 Star Review

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 g.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 5.0 Star Review

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-fo.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Cudjoe Key

Cudjoe Key Vacation Rental 4.7 Star Review

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. Thi.......read more

6 Bedrooms - Sleeps 14
Vacation Rental Home in Cudjoe Key