
Vacation rentals with a kayak in Islamorada
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Islamorada
Guests agree: these kayak rentals 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.

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

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!

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 💫

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.

Large Waterfront Home, w/Efficiency, Pool, Kayaks
Large Waterfront home completely renovated in gated upscale community. 2/2 upstairs and complete 1/1 efficiency downstairs. Highest Airbnb Rating in the area. Only 12 houses away from the Bay and near many restaurants and attractions. BRAND NEW POOL along with new GAZEBO and BBQ area (Not shown it some pictures). Enjoy sunset cruises, island hopping and dock-side dining. 60' of waterfront, large dock and 2 kayaks available. pontoon rental available for Bayside only. Must be 25 or older.

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 Getaway - Kayaks - 2BR 2.5BA Villas
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.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

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.
Popular amenities for Islamorada kayak rentals
House rentals with a kayak

Oceanside, Fee-Less Pet, with kayaks - 60 FT Dock

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

Luxury Waterfront Retreat with Dockage & Pool

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Off the Hook~ Luxury Pool Home, 30' Dock & Kayaks!

Waterfront Paradise Key Largo. Casa Luna

Ocean Shores Villa 1 with Pool and Boat Slip

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!
Cottage rentals with a kayak

Waterfront Getaway | Kayaks, Private Dock & BBQ

Islamorada bungalow 2 bed & pool

Oceanfront Getaway | Kayaks, BBQ & Stunning View!

Kampground Paradise w/Kayaks, Heated Pool & Marina

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Cottage Sunroom Waterfront Retreat 2 ppl

Keys Waterfront Oasis • Tiki • Private Pool • Dock

THE PARADISE
Other vacation rentals with a kayak

Keys Relaxing Getaway

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

Tropical 2BR/2BA Getaway in Gorgeous Key Largo

New! Waterfront Views | Pool & Tiki Bar

Waterfront Key Largo Home - Tropical Paradise

Waterfront home w/pool, dock & close to beach

Waterfront Private Home w/Pool-Family&Pet Friendly

Remodeled July 2025 2/2 Townhouse
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,744 | ﺩ.ﺇ1,491 | ﺩ.ﺇ1,414 | ﺩ.ﺇ1,285 | ﺩ.ﺇ1,285 | ﺩ.ﺇ1,366 | ﺩ.ﺇ1,227 | ﺩ.ﺇ1,153 | ﺩ.ﺇ1,161 | ﺩ.ﺇ1,429 | ﺩ.ﺇ1,546 |
| 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 vacation rentals with a kayak in Islamorada

Total vacation rentals
Explore 100 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at ﺩ.ﺇ588 per night before taxes and fees

Verified guest reviews
Over 1,870 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
100 of Islamorada vacation 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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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
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- Key Largo Kampground And Marina
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- Founder's Park




