
Vacation rentals with a kayak in Florida Keys
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Florida Keys
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

Sunrise Escape - Ocean Front Villa - Sleeps 10
Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking/paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, or walking to the beach jetty just across the marina. Or take a swim/snorkel in our swimmable lagoon or one of our two pools. Then bring a glass of wine to watch the breathtaking sunsets from our o

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg
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.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Amazing houseboat with 2nd floor observation deck
Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

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.

Key Largo Waterfront Retreat | Tiki, Dock & Pool
This waterfront retreat is perfect for couples, families, or boaters looking to explore the best of the Keys. Snorkel right from the dock, paddle through mangroves with the included kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, and a sandy beach, plus only 0.3 miles from groceries and restaurants. Whether you’re fishing, diving famous reefs, or just unwinding under the tiki, this home puts paradise at your doorstep.

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.

*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.

Modern beach tiny house/Tiki hut/ boat dock 20ft
Modern beach 'Tiny House" cottage on Canal in key largo. Great location for boaters, fisherman and includes 20ft private dock. Great area to kayak, paddle board or fish. Private Tiki hut just steps from the water. Two kayak's included for your use. This is great community which includes private ramp and associotion pool for homeowners. Very close to private beaches only accessible by boat. Well behaved pets allowed

Key Largo! Tavernier! Welcome to Paradise!
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 )
Popular amenities for Florida Keys kayak rentals
House rentals with a kayak

Waterfront Escape -VACA-23-408

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Yellowtail Getaway with Boat Dock and Pool 2

Spacious lux home, private pool/spa, 80' dock

Emerald Oasis ~ Lux Waterfront Gem ~ Heated Pool ~

Private Pool! Luxury Paradise Pointe, Pet Friendly

Modern Beach Lake-Front House in Miami !

Dock Pool Home by Sombrero Beach
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

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

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

Beautiful 3 bedroom cottage with private rooftop

OCEANIA... water front cottage retreat ~

THE PARADISE

Welcome to the Islands- Pool-Marina-Kayak
Other vacation rentals with a kayak

Kokomo - Waterfront Tiny House/Tiki/Boat Lift/Dock

Reel Hip– Heated Pool, Boat Slip, Heat, King Bed

Waterfront Miami Oasis w/ Kayaks | Heated Pool

Flamingo Palms-NOV/DEC discounts on AVAIL DATES

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Golf Coast Oasis

5-Star Water Front Luxury Home

Pet Friendly Half-Duplex Cottage w/40' Slip Option
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- Saint Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Townhouse rentals Florida Keys
- Guesthouse rentals Florida Keys
- Mansion rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Boutique hotel rentals Florida Keys
- Houseboat rentals Florida Keys
- Condo rentals Florida Keys
- Ski-in/ski-out rentals Florida Keys
- Cottage rentals Florida Keys
- Tiny house rentals Florida Keys
- Fitness-friendly rentals Florida Keys
- Rentals with lake access Florida Keys
- Campsite rentals Florida Keys
- Boat rentals Florida Keys
- Waterfront rentals Florida Keys
- Rentals with beach access Florida Keys
- Rentals with an accessible height bed Florida Keys
- Bed and breakfasts Florida Keys
- House rentals Florida Keys
- RV rentals Florida Keys
- Rentals with pools Florida Keys
- Bungalow rentals Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Rentals with a patio Florida Keys
- Rentals with an EV charger Florida Keys
- Rentals with a fireplace Florida Keys
- Rentals with breakfast Florida Keys
- Serviced apartment rentals Florida Keys
- Hotel rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Villa rentals Florida Keys
- Beach house rentals Florida Keys
- Beachfront rentals Florida Keys
- Luxury rentals Florida Keys
- Rentals with a washer and dryer Florida Keys
- Smoking-friendly rentals Florida Keys
- Private suite rentals Florida Keys
- Vacation home rentals Florida Keys
- Rentals with a fire pit Florida Keys
- Family-friendly rentals Florida Keys
- Rentals with a sauna Florida Keys
- Beach condo rentals Florida Keys
- Resort rentals Florida Keys
- Rentals with a home theater Florida Keys
- Pet-friendly rentals Florida Keys
- Apartment rentals Florida Keys
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Bayfront Park
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Phillip and Patricia Frost Museum of Science
- Biltmore Golf Course Miami
- Crandon Beach
- Key Biscayne Beach
- Biscayne National Park
- Coral Castle
- Cocoa Plum Beach
- Hobie Island Beach Park North
- Cannon Beach
- Fairchild Tropical Botanic Garden
- Matheson Hammock Park
- Conch Key
- Venetian Pool
- Theater of the Sea
- Far Beach
- Deering Estate
- Virginia Beach
- Sea Oats Beach
- Everglades Alligator Farm
- Things to do Florida Keys
- Art and culture Florida Keys
- Food and drink Florida Keys
- Sightseeing Florida Keys
- Sports activities Florida Keys
- Nature and outdoors Florida Keys
- Tours Florida Keys
- Things to do Florida
- Wellness Florida
- Food and drink Florida
- Entertainment Florida
- Tours Florida
- Sightseeing Florida
- Sports activities Florida
- Art and culture Florida
- Nature and outdoors Florida
- Things to do United States
- Sightseeing United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Art and culture United States
- Wellness United States
- Food and drink United States
- Tours United States