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.

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Guest favourite
Houseboat in Islamorada Tavernier
4.89 out of 5 average rating, 257 reviews

Florida Keys Houseboat, unique waterfront stay-

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

Top Guest favourite
Condo in Tavernier
4.96 out of 5 average rating, 211 reviews

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.

Guest favourite
A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.
Tiny home in Key Largo
4.96 out of 5 average rating, 180 reviews

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.

Top Guest favourite
A heated swimming pool is surrounded by palm trees and lounge chairs. The pool area includes a smaller heated kiddie pool, with seating arrangements featuring bright blue chairs. The spacious layout ensures an inviting setting for relaxation.
Townhouse in Key Largo
4.98 out of 5 average rating, 105 reviews

Fun the Keys! Pool, Marina, Clubhouse, Fishing & m

Spend your vacation on the bayside of Key Largo, with the best sunsets to end your day. Steps away from the heated swimming pool and kiddie pool. Walk to a strip of restaurants on the water and enjoy a gorgeous sunset. We have the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer. Come enjoy the island life in your comfortable and clean vacation house, on a property with everything you need, just bring your groceries! Two bedrooms with private bathrooms.

Top Guest favourite
A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.
Villa in Duck Key
4.96 out of 5 average rating, 170 reviews

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.

Top Guest favourite
Condo in Key Largo
4.89 out of 5 average rating, 178 reviews

Tropical Getaway

This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.

Top Guest favourite
A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.
Tiny home in Key Largo
4.97 out of 5 average rating, 186 reviews

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.

Top Guest favourite
A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.
Home in Key Colony Beach
4.96 out of 5 average rating, 134 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.

Guest favourite
A bright studio space features a plush queen-sized bed and a cozy seating area with a Roku-enabled TV. The modern kitchen includes bar seating. Balconies overlook water views and a communal pool area, while tiki huts provide shaded outdoor lounging. Kayaks and paddle boards are readily available.
Apartment in Key Largo
4.92 out of 5 average rating, 296 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Top Guest favourite
The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.
Boat in Islamorada
4.93 out of 5 average rating, 371 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
Home in Key Largo
4.97 out of 5 average rating, 174 reviews

Key Largo Waterfront: Tiki, Dock, Kayak & 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 tandem 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.

Top Guest favourite
A serene canal-front dock area is shown, featuring several white, wooden lounge chairs arranged for relaxation. Kayaks in vibrant colors are secured nearby, surrounded by lush greenery and calm waters reflecting the clear blue sky.
Guest suite in Tavernier
4.98 out of 5 average rating, 329 reviews

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 Islamorada kayak rentals

When is the best time to visit Islamorada?

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Avg. price$669 NZD$795 NZD$679 NZD$644 NZD$586 NZD$586 NZD$622 NZD$559 NZD$525 NZD$529 NZD$651 NZD$704 NZD
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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 $268 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,870 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

    70 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, Wifi 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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