
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.

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.

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.

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.

Kawama R5 Pool view free bikes & kayaks
Experience island living at its best in this fully furnished, modern condo with a spacious layout and luxurious amenities. Relax by the pool or take a dip in the saltwater lagoon. Enjoy the convenience of having a marina, two heated pools, a kids playground, and tennis and pickleball courts just steps away from your door. For your convenience we provide two bikes and two kayaks to explore the surroundings. Come relax, unwind and make memories that will last a lifetime. Book your stay now!

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.

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 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!

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! 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 )

Oceanfront Getaway | Kayaks, BBQ & Stunning View!
Imagine yourself "Paradise Living" at this completely remodeled modern Oceanfront Tiki Stay! Enjoy the beautiful Florida Keys in the relaxing community of Manatee Bay! This oceanfront tiny home feels just like your home away from home. Located right at the entrance of Monroe County, this hidden gem is just off Mile Marker 112 in Key Largo, FL. Booking relaxation is just a click away!

Reel Large END Unit in Ocean Point Suites
Paradise awaits you in this large END unit, 2 BR/2BA in the highly desirable community of Ocean Pointe Suites! Newly renovated Modern Beach decor unit with breathtaking views from our Private beach and Marina are just a few highlights of this island retreat. Restaurant/Bar on site with beautiful views of the ocean. Live band and happy hour daily.
Popular amenities for Islamorada kayak rentals
Holiday House Rentals with a Kayak

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

Tropical 2BR/2BA Getaway in Gorgeous Key Largo

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Waterfront Home 37.5-ft dock, Cabana Club Included

Chasing Sunrises | Family Style

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

Private Pool! Luxury Paradise Pointe, Pet Friendly

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!
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

Tropical House By The Shore at Largo Resort

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Cottage Sunroom Waterfront Retreat 2 ppl

Keys Waterfront Oasis • Tiki • Private Pool • Dock
Other holiday rentals with a kayak

Angler’s Reef home • Pool • Kayaks • Paddle boards

Marathon Keys Escape • Pool • Hot Tub • Near Beach

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

Key Largo downstairs guest house

Isla Mirabelle: FREE Boat Dockage Sep-Oct Only!

Studio apartment in Calusa Resort & Campgrounds

Pet Friendly (Fee-Less) Half-Duplex Cottage

Oceanfront Hot Tub. Sunset Escape.
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $568 AUD | $674 AUD | $576 AUD | $547 AUD | $497 AUD | $497 AUD | $528 AUD | $474 AUD | $446 AUD | $449 AUD | $552 AUD | $598 AUD |
| 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 $227 AUD 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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- Rentals with a kayak Monroe County
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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
- Long Beach
- Everglades Alligator Farm
- Conch Key
- Bahia Honda State Park
- Theater of the Sea
- Homestead-Miami Speedway
- Monkey Jungle
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Calusa Campground
- Sunset Park
- Robbies Marina Of Islamorada
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Founder's Park




