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

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

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.

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.

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.

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: 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.

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACKETS/BALLS AND FISHING GEAR in a private beach resort community with a fishing jetty, a 24/7 boat ramp & a 3-acre salt-water lagoon for swimming, snorkeling, kayaking & paddleboarding. The condo sleeps 6 & is in the gated Kawama Community of Key Largo, surrounded by JOHN PENNEKAMP CORAL REEF STATE PARK. Marina boat slips may be available for rent.

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 kayak rentals in Islamorada
House rentals with a kayak

Discount Available! Pool 100' Dock, Fun Amenities!

The Roseate House at Grassy Key Lic. #VACA-25-222

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Waterfront Home 37.5-ft dock, Cabana Club Included

Sea Glass Beach Bungalow in Key Colony Beach!

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

Pet Friendly (Fee-Less) Half-Duplex Cottage

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
Cottage rentals 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

Keys Relaxing Getaway

Moon Bay Key Largo | Sunset Views | 24' Boat Lift

Waterfront Oasis w/Private Pool-Dockage-Beach

The property has a breath taking view of the bay

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Yellowtail Getaway with Boat Dock and Pool 2

b watervibe

Luxury Boating Paradise+Pool+Sailing Kayaks
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $514 SGD | $611 SGD | $522 SGD | $495 SGD | $450 SGD | $450 SGD | $478 SGD | $429 SGD | $404 SGD | $404 SGD | $456 SGD | $526 SGD |
| 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 $206 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
100 of Islamorada holiday rentals include wifi 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
- The Turtle Hospital
- Coral Castle
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Everglades Alligator Farm
- Conch Key
- Long Beach
- Theater of the Sea
- Monkey Jungle
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Calusa Campground
- Dolphin Research Center
- Robbies Marina Of Islamorada




