We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals with a kayak in Cudjoe Key

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Cudjoe Key

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Houseboat in Key West

4.83 out of 5 average rating, 281 reviews

Key West Houseboat Paradise

New Houseboat- Queen Bed, Full Kitchen, Big Living Rm, Full Bath & 3 Sun Decks. $200k comprehensive rebuild in 2022. Tucked away on an old wooden dock on Stock Island, 15 min from dwntwn Key West. Vibe is 'Old-School Key West' locals-only. Property has an industrial feel including the classic 2-bay, grumpy old curmudgeon auto garage/carwash & a warehhouse so Shore Side 'aint fancy. But, your back deck view is a mile-wide ocean channel, dozens of mangrove islands and a pair of 12' Sea Kayaks...

Houseboat in Tavernier

4.88 out of 5 average rating, 217 reviews

Clean Fully Remodled Houseboat Luxery on the water

Very spacious, Comfortable and "super clean" Houseboat. Rent daily “Baycation” is a 44'x15' triple level upper deck Houseboat completely remodeled. This is an adventure, unlike any hotel room! Live on the water, in an amazing marina, with so much to do you need to come back! Sleep like you never have before, all my guests tell me that! Bonus Lay on the upper deck and see the amazing star ambiance...... This is for everyone......Couples, families & just friends, Its perfect

Home in Cudjoe Key

4.91 out of 5 average rating, 75 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there. Also see our other paradise, http://airbnb.com/h/keysshangrila

Home in Cudjoe Key

4.92 out of 5 average rating, 12 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

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. This is #107 and I also rent adjacent homes 111 and 109 in case you need more than one. We are 120 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Cottage in Islamorada

4.82 out of 5 average rating, 162 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Boat in Islamorada

4.92 out of 5 average rating, 331 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Home in Cudjoe Key

4.82 out of 5 average rating, 66 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Home in Cudjoe Key

4.86 out of 5 average rating, 70 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Home in Cudjoe Key

4.82 out of 5 average rating, 243 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Home in Key Colony Beach

4.98 out of 5 average rating, 108 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!

Guest suite in Tavernier

4.97 out of 5 average rating, 268 reviews

POOL ! Key Largo! Tavernier! Welcome to Paradise!

POOL! A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )

Home in Cudjoe Key

4.81 out of 5 average rating, 27 reviews

Yellow Vacation home, Free cancelation see details

Beautiful house nestled off of US 1. Kayaks included in the rental. Rent one or both of our other properties that are near each other for a great full family vacation. All 3 properties are listed on AirBNB. Private heated pool with seats inside of the pool to enjoy the view. We provide bedding, towels, pots and pans. Home with water access/dock for a small boat.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Cudjoe Key kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Marathon

4.98 out of 5 average rating, 59 reviews

Sombrero beach oasis,great location,many amenities

Home in Marathon

5 out of 5 average rating, 35 reviews

Yellowtail Getaway with Boat Dock and Pool 2

Home in Key Colony Beach

4.94 out of 5 average rating, 98 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Home in Marathon

5 out of 5 average rating, 28 reviews

Luxury Boating Paradise+Pool+Steps to Snorkeling

Home in Marathon

4.94 out of 5 average rating, 34 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

Home in Marathon

5 out of 5 average rating, 70 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

Home in Marathon

4.95 out of 5 average rating, 21 reviews

Waterfront w/pool and hot tub

Home in Marathon

4.98 out of 5 average rating, 41 reviews

Waterfront Heated Pool 120 ft Boat Dock

Cottage rentals with a kayak

Cottage in Cudjoe Key

4.84 out of 5 average rating, 93 reviews

OCEANIA... water front cottage retreat ~

Cottage in Islamorada

4.96 out of 5 average rating, 56 reviews

Islamorada bungalow 2 bed & pool

Cottage in Cudjoe Key

4.71 out of 5 average rating, 131 reviews

Calypso Cottage

Cottage in Marathon

4.96 out of 5 average rating, 24 reviews

Catch n' Relax Canalfront Cottage in Marathon

Cottage in Islamorada

New place to stay

Cottage on Bayfront Estate – Pool, Beach, & Dock

Cottage in Cudjoe Key

4.92 out of 5 average rating, 98 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Cottage in Key Colony Beach

5 out of 5 average rating, 10 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

Quick stats about vacation rentals with a kayak in Cudjoe Key

Total rentals
40 properties
Nightly prices starting at
$170 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore