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

New Tinyhouse RV, Kayak, Beach, Fish, Marina, Pool
Newly replaced RV, lot# 19 at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed in loft, living room Sofa bed, lounging basement, Full Kitchen and Full Bathroom, Cable TV and Wi-Fi. In walking distance to Publix Supermarket, John Pennekamp State Park, deep sea Fishing, Diving and Snorkel Charter boats, Restaurants. Private nicely landscaped all-to-your-self lot approx. 40' x 60' and it's, conveniently near the pool, boat ramp w/ trailer parking, laundry, toilet- bath house

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.

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.

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.

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.
Popular amenities for Windley Key kayak rentals
House rentals with a kayak

Waterfront with Boat Lift/Kayaks and Hot Tub

Tropical 2BR/2BA Getaway in Gorgeous Key Largo

Waterfront Key Largo Home - Tropical Paradise

Waterfront home w/pool, dock & close to beach

Waterfront w/pool and hot tub

Remodeled July 2025 2/2 Townhouse

The Mini Coconut

Tropical Waterfront, Boat Dock, Sunset View, Kayak
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

Kawama L1 Relaxing Lagoon View free bikes & kayaks

Waterfront Key Largo Escape | Boat Slip Included

b watervibe

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Viamarhe Cabin-Private beach, Kayak, yard games

Studio apartment in Calusa Resort & Campgrounds

Waterfront Paradise Key Largo. Casa Luna

Beautiful Kawama Townhouse
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