Cudjoe Key Vacation Rentals, Cottages and Beach House Rentals.
Book Your Vacation Rentals Here Securely and Save!
Vacation Rentals by Owner in Cudjoe Key Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida.
A slice of paradise
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.
Bathroom does connect to oe bedroom.
There is a queen bed in the bottom floor be.......
Quaint cottage, pool, dockage just minutes to Key West!
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.......
9.0 Star Review
2 Bedrooms
- Sleeps 4
Cudjoe Key Vacation Rental
Pets Allowed 
Cottage with swimming pool and dockage, just minutes to Key West!
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 .......
9.0 Star Review
1 Bedrooms
- Sleeps 2
Cudjoe Key Vacation Rental
Pets Allowed
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
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 .......
8.6 Star Review
1 Bedrooms
- Sleeps 2
Cudjoe Key Vacation Rental
Pets Allowed
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
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. We are one of only a handful of houses in Venture Out that is secluded with no neighbors directly across the canal. Tropical fish viewing at the seawall and you never know when you will see a manatee swimming by. Fishing for mangrove snapper is also easy from th.......
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View
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.......
9.8 Star Review
2 Bedrooms
- Sleeps 6
Cudjoe Key Vacation Rental
Pets Allowed
Waterfront, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w/ shower!
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 .......
Fandango - private pool
This is a pet friendly home. A pet fee and approval of your pet is required.
This house includes all the elements you need for an amazing vacation. Outside the house there are kayaks for adventures, a swimming pool, Hot tub, private beach area with loungers and Beach chairs for relaxation, a floating dock for fishing and docking a boat up to 24’, tropical foliage including coconut palms and bananas, a screened in porch for dining al fresco and so much more.
Your property manager lives nearby and is available if you have any requests during your stay
Quiet.......
9.8 Star Review
5 Bedrooms
- Sleeps 12
Cudjoe Key Vacation Rental
Pets Allowed
Sirena Key Cottage in Venture Out
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.......
Casa Del Mar in Venture Out Unit 253
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.......
Venture Out Million Dollar Ocean View
Oceanfront 2BR , King or 2 Twins . Extra guest has a queen sofa sleeper, featuring bright coastal décor and wide open. Relax with soft Ocean Breezes and fantastic Sunset views. Enjoy two resort pools, tennis courts and more. Great large dock for fishing or boating, and a BBQ area for easy outdoor living. A modern kitchen, spacious living room, and unbeatable ocean access to nearby tropical islands create the perfect Keys escape close to beaches, dining, and island attractions........
9.4 Star Review
2 Bedrooms
- Sleeps 6
Cudjoe Key Vacation Rental
Pets Allowed
Cudjoe Bay Getaway In Paradise
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.
The Rental Details: 28 day minimum for all bookings.
The Kitchen/Living Area: We.......
9.4 Star Review
3 Bedrooms
- Sleeps 6
Cudjoe Key Vacation Rental
Pets Allowed
Cottage with Pool and Boat Dockage just minutes to Key West!
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.......
8.6 Star Review
1 Bedrooms
- Sleeps 2
Cudjoe Key Vacation Rental
Pets Allowed
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.......
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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........
8.8 Star Review
3 Bedrooms
- Sleeps 6
Cudjoe Key Vacation Rental
Pets Allowed
Seascape Vacation!!!
Beautiful vacation spot 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.Great place to relax and have a drink by the dock.You can dock a boat up to 15 ft. Overflow parking for boat trailers and extra vehicle is available on a first come first serve bases and is not guaranteed.......
Seas The Day 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. Staying here you`ll most definitely have a fun time! VO REGISTRATION FEE $125.00 DUE UPON ARRIVAL. Overflow parking for boat trailers and extra vehicle is available for an additional fee and is available on a first come first serve bases and is not guaranteed........
Family Retreat Ocean front pool
6 Bedroom 4 bath
Rental Rates are based on the number of guests. Base rate is for 6 guests. There is an additional charge of $25 per night per person over 6 guests.
This home can be rented as a 3 bedroom home for a reduced rate or a 6 bedroom home.
Ocean front with pool and a dock for your boat up to 24'
Your property manager lives nearby and is available if you have any requests during your stay
This is a quiet neighborhood in a residential area
This is a pri.......
9.4 Star Review
5 Bedrooms
- Sleeps 14
Cudjoe Key Vacation Rental
Pets Allowed
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Minimum Rental is 28 Days to a single family or party (no subleases allowed).
Simply Breathtaking VIEWS of the sunset over the ocean like this right from this home and from the deck.
2 Bedroom 2 Bathroom Home with Ocean Front Views Sleeps 4 adults comfortably . Fisherman's grand slam! You have your own dock and boat ramp. Vaulted wood ceilings with a classic cottage feeling. The porch will be the perfect place to watch the best sunsets and wild life in the lower keys over the open w.......
Springs Venture Out Dolphin House #386 with beautiful open water views
This Home has some of the absolute best views of the Ocean; sitting on your deck watching nature at its best. Our 35ft sea wall perfect for fishing or docking your boat.
Easy access to either the Atlantic or the gulf; some of the best fishing or lobstering spots located in all of the Keys. Plus one of the most beautiful Light Houses located just a short Boat ride to a awesome light house with great snorkeling opportunities.
Also some of best food located just around the corner(Square Group.......
Island Therapy
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities include central air conditioning, new tile floor, new furnishing and decorations throughout, wireless internet, flat screen television, washer, dryer, dishwasher, microwave and covered porch. Master bedroom has a queen bed with lots of closet storage, flat screen television and private full bathroom. Guest bedroom has a queen bed with full length closet storage, private full bathro.......
SHORT TERM RENT WITH 10k BOAT LIFT Avail from 5/1/2026 for 5-6 months
2 Bedrooms/2 Bathroom home ready for move in May 2026. Property has an open concept living space with tiling throughout, shower and soaking tub. No pets preferred, possible on approval of breed with non-refundable $250 pet fee. (Small pets only, call please) Utilities (water and electric) are tenant responsibility. First and last months rent and security deposit to move in. Prefer 6 month rental, but negotiable. Serious inquiries only -
2 good size bedrooms both with queen beds and one w.......
2 Bedrooms
- Sleeps 10
Cudjoe Key Vacation Rental
Pets Allowed
Relax by Florida Keys Beaches, just a 7-min drive away
In beautiful Summerland Key, you'll find our lovely two-bedroom getaway that showcases stunning Florida Keys scenery. Situated just a 7-minute drive from the stunning Florida Keys Beaches, you'll be able to easily access the area's pristine white sand and turquoise waters. Spend your days lounging by the outdoor pool or unwinding in the soothing hot tub. Back at the house, you'll enjoy the convenience of free WiFi, a smart TV with satellite/cable channels, and a full-size washer and dryer. The f.......
9.8 Star Review
2 Bedrooms
- Sleeps 5
Cudjoe Key Vacation Rental
Pets Allowed
Looking for a place to stay?
Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and snorkeling has never been easier. Easy access to Content Islands.
The home is conveniently located on Cudjoe Key, MM23, allowing for a 25 minute drive to famous Duval Street in Key West, or Maratho.......
Enjoy Caribbean weather in the USA. Openings June 2026 forward!
We have a big bright eat in fully stocked kitchen. Kitchen has many pots and pans, keurig, blender, glassware and most things that you’ll be looking for while relaxing in the beautiful Keys!! The main bedroom has a KING size bed, lots of storage space and TV with YouTube Live TV & Roku.
The second bedroom has a twin trundle, when the two twin beds are side by side it's like another King Size Bed and TV with Roku & streaming YouTube Live TV.
.......
Fisherman's Paradise
Unwind in a brand new, modern and luxurious, waterfront home with great views and a deep water canal in Cudjoe Key Florida. Fisherman's Paradise has three bedrooms, three baths, and can sleep up to 14 guests. It is located just twenty minutes away from world renowned Key West, and the beach at Ft. Zachary Taylor State Park. Nearby Bahia Honda State Park also has a great beach. This beautiful home features upscale furnishings, spacious living areas, and a complete and relaxing outdoor space. The .......
Paradise in the Lower Keys!
Tropically Decorated Stilt Home
Lovely Covered Porch with Water View
You won't be disappointed in the beautiful decorated 2 Bedroom/2 Bath stilt home with a canal view. Relax on the covered deck with privacy palms. Lovely tropical decor with a nice size living room and dining area. Sleeping accommodations include a Queen size bed in the Master bedroom with its own private bath, a full size bed in the Guest bedroom with a small balcony, and a Queen size sleeper sofa in the living room. Am.......
2 Bedrooms
- Sleeps 6
Cudjoe Key Vacation Rental
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Come stay with us at VENTURE OUT, a fantastic gated, activity filled community in Cudjoe Key, Fl- only 20 miles north of Key West! This updated 2 Bedroom, 2 bath, King Master and elevated waterfront property with 35' Seawall has THE BEST VIEWS from inside, from the screened porch and has a lower covered and plenty of shaded space to hang out and grill- plus a storage room with an extra refrigerator and bait freezer for all the guys fixins! And your vehicle under 82" can also be covered and shade.......