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

Florida Keys Dockside Paradise, Luxury Houseboat
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

Modern Beach Lake-Front House in Miami !
Welcome to our stunning 5/4 beachfront lake house! This newly renovated property offers the perfect blend of modern amenities and natural beauty. Located in a central and peaceful neighborhood, guests can enjoy a range of water activities such as kayaking, paddle boarding, and swimming while taking in the views of the Blue lake. Seeking relaxation or adventure, this home has something for everyone.. ✔️15min from Miami International airport ✔️25min to Downtown Miami ✔️30min from Miami Beach

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.

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.

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.

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.

*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.

Hunter 26 Sailboat
A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

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 kayak rentals in Monroe County
House rentals with a kayak

Blue House - Receive $400 towards a Boat Rental!

Large heated Pool Home (Centrally Located)

CASA PALMA Golf Cart, Kayaks, Pools, Beach,2 Kings

Sunset Views, Pool and Dock

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Oct. Special 50% off! Oceanfront, 4 Bikes 2 Kayaks

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool

Ocean Breeze at Venture Out 537

Cottage on Bayfront Estate – Pool, Beach, & Dock

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

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

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

OCEANIA... water front cottage retreat ~

THE PARADISE
Other holiday rentals with a kayak

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

Pristine pool front home w/ocean views Anglers 148

Palm - Beach Houses Key West

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

Panoramic Oceanside Luxury, Dockage & Gameroom

Viamarhe House-Private beach, Kayak, yard games

Key West Houseboat Paradise

House boat unique experience!
Destinations to explore
- Rentals with a patio Monroe County
- Villa rentals Monroe County
- Fitness-friendly rentals Monroe County
- Townhouse rentals Monroe County
- Beachfront rentals Monroe County
- Farm stay rentals Monroe County
- Hostel rentals Monroe County
- Rentals with a sauna Monroe County
- Campsite rentals Monroe County
- Tiny house rentals Monroe County
- Aparthotel rentals Monroe County
- Ski-in/ski-out rentals Monroe County
- Rentals with pools Monroe County
- Bed and breakfasts Monroe County
- Rentals with breakfast Monroe County
- Rentals with an accessible-height toilet Monroe County
- Flat rentals Monroe County
- House rentals Monroe County
- Rentals with an accessible-height bed Monroe County
- Guest house rentals Monroe County
- Rentals with lake access Monroe County
- Waterfront rentals Monroe County
- Rentals with beach access Monroe County
- Rentals with a firepit Monroe County
- Cottage rentals Monroe County
- Luxury rentals Monroe County
- Houseboat rentals Monroe County
- Smoking-friendly rentals Monroe County
- Motorhome rentals Monroe County
- Rentals with outdoor seating Monroe County
- Apartment rentals Monroe County
- Serviced apartment rentals Monroe County
- Loft rentals Monroe County
- Family-friendly rentals Monroe County
- Hotel rentals Monroe County
- Rentals with an EV charger Monroe County
- Rentals with a washing machine and dryer Monroe County
- Rentals with a cinema Monroe County
- Resort rentals Monroe County
- Rentals with a fireplace Monroe County
- Rentals with a hot tub Monroe County
- Pet-friendly rentals Monroe County
- Private suite rentals Monroe County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Coral Castle
- Cannon Beach
- Calusa Beach & Loggerhead Beach
- Cocoa Plum Beach
- Conch Key
- Theater of the Sea
- Everglades Alligator Farm
- Far Beach
- Monkey Jungle
- Sea Oats Beach
- Horseshoe Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Keys' Meads
- Long Beach
- Sandspur Beach
- Schnebly Redland's Winery & Brewery
- Things to do Monroe County
- Tours Monroe County
- Nature and outdoors Monroe County
- Art and culture Monroe County
- Food and drink Monroe County
- Sightseeing Monroe County
- Entertainment Monroe County
- Sports activities Monroe County
- Things to do Florida
- Art and culture Florida
- Tours Florida
- Sports activities Florida
- Entertainment Florida
- Nature and outdoors Florida
- Sightseeing Florida
- Food and drink Florida
- Wellness Florida
- Things to do United States
- Entertainment United States
- Art and culture United States
- Sightseeing United States
- Sports activities United States
- Tours United States
- Wellness United States
- Nature and outdoors United States
- Food and drink United States