
Holiday rentals with a kayak in Islamorada
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Islamorada
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Island Sanctuary Islamorada
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

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

Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 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!

Best View Ocean Pointe Pool Beach King Bed, Gated
***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

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.

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.

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

Ocean Shores Villa 2 with pool and boat slip
This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boatslip,kayaks,bikes,fire pit,hammock and heated pool). 32ft dock slip and trailer parking are included in the rental. Conveniently located near Sandbars, State Parks and many attractions.
Popular amenities for Islamorada kayak rentals
Holiday House Rentals with a Kayak

Discount Available! Pool 100' Dock, Fun Amenities!

Paradise found!Key Colony Beach,Cabana Club.

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

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Remodeled July 2025 2/2 Townhouse

Golf Coast Oasis

Serenity Oasis~Pool!~Kayaks~Grill~Bikes~Spa
Cottages with a kayak

Waterfront Getaway | Kayaks, Private Dock & BBQ

Islamorada bungalow 2 bed & pool

Keys Cottage with Sleeping Loft| Sleeps 6

Kampground Paradise w/Kayaks, Heated Pool & Marina

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Cottage Sunroom Waterfront Retreat 2 ppl

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

THE PARADISE
Other holiday rentals with a kayak

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

b watervibe

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

Salt&Seaglass. Key Colony. Screen Porch. Pool Club

5-Star Water Front Luxury Home

House boat unique experience!

Beautiful Kawama Townhouse

Waterfront Paradise Key Largo. Casa Luna
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $699 NZD | $830 NZD | $710 NZD | $673 NZD | $612 NZD | $612 NZD | $699 NZD | $666 NZD | $524 NZD | $561 NZD | $620 NZD | $715 NZD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals with a kayak in Islamorada

Total holiday rentals
Explore 100 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $245 NZD per night before taxes and fees

Verified guest reviews
Over 1,850 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
100 of Islamorada holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Islamorada rentals

4.9 Average rating
Islamorada stays are highly rated by guests—averaging 4.9 out of 5!
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