Holiday rentals with a kayak in Key West

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Top-rated Accommodation with a Kayak in Key West

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Superhost

Houseboat in Key West

4.81 out of 5 average rating, 324 reviews

Key West Houseboat Paradise

5 Years SuperHost Rated with over 300 reviews!! ~ Single Stateroom with Queen Bed, ideal for a couple. Sleeps 1-4. Spacious living room, big sofas. Full kitchen, Full Bath, large Rooftop Sun Deck, 15 min to Duval St. The land-side isn't fancy. Light industrial, Old-school Key West feel. Blue collar, friendly working class, wooden dock with a working auto garage & warehouse but the water view of dozens of green mangrove island with 2 Sea Kayaks waiting for you to take exploring is a Hidden Gem.

Guest favourite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 131 reviews

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

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Guest favourite

Home in Key Colony Beach

4.95 out of 5 average rating, 21 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

Beautiful Key Colony Beach waterfront duplex with a private pool! Featuring a newly updated, 3/2, spacious 1440 sf home, deep water private boat slip & lift, Tiki Hut w/TV, kayaks, pet friendly, ice machine, bait freezer, large kitchen, Cabana Club, restaurant, and beach access. Family friendly location w/Golf, a playground, and dog park. Sit under the tiki hut, watch the game on the outdoor TV after a day on the water, & grill your catch. Relax on the upper deck sunbathe and enjoy the vistas!

Guest favourite

Villa in Duck Key

4.95 out of 5 average rating, 144 reviews

Beach House - Kayaks & 2/2.5 Villa

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Guest favourite

Houseboat in Key West

4.95 out of 5 average rating, 125 reviews

Full houseboat with large observation deck

We invite you to stay at our unique houseboat “Wild One”. Wild One is anchored minutes (by boat) from Garrison Bight Marina which is at the heart of Key West. Rides will be given to and from Wild One at the beginning and end of your stay. We will provide one in and out ride per day during your stay. Ride times must also work around our charter schedule which you will be advised of. Rides can be requested after nightfall but are accepted on a case to case basis. Last ride is at 10pm

Top Guest favourite

Home in Key Colony Beach

4.95 out of 5 average rating, 118 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Top Guest favourite

Boat in Islamorada

4.93 out of 5 average rating, 350 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.

Top Guest favourite

Houseboat in Key West

4.96 out of 5 average rating, 23 reviews

Shanty Pineapple Key West

Indulge in an unforgettable, sensual escape aboard our private off-grid houseboat in Key West. Perfect for couples seeking to reignite passion or explore new adventures together, this secluded floating retreat offers an intimate, exclusive setting where every moment is infused with romance and possibility. Whether you’re here to reconnect, explore each other’s desires, or simply escape the world, the serene waters and intimate atmosphere make this the ultimate romantic playground

Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 101 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!

Guest favourite

Home in Upper Sugarloaf Key

4.94 out of 5 average rating, 95 reviews

Lighthouse - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

Guest favourite

Houseboat in Marathon

4.89 out of 5 average rating, 121 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 109 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.