Holiday rentals with a kayak in Lower Matecumbe Key

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Top-rated rentals with kayak in Lower Matecumbe Key

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite

Boat in Tavernier

4.91 out of 5 average rating, 378 reviews

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.

Top guest favourite

Houseboat in Islamorada Tavernier

4.89 out of 5 average rating, 243 reviews

September Special- Luxury Houseboat vacation

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

Guest favourite

Tiny home in Key Largo

4.96 out of 5 average rating, 157 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

Villa in Duck Key

4.95 out of 5 average rating, 152 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

Tiny home in Key Largo

4.97 out of 5 average rating, 150 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

Boat in Islamorada

4.93 out of 5 average rating, 355 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, 162 reviews

Boaters, Bring Your Boat to our Keys Private Dock

WATERFRONT KEY LARGO RETREAT WITH PRIVATE TIKI DOCK Your slice of paradise in a bright and airy Key Largo waterfront home. Sip morning coffee or sunset drinks under the tiki, snorkel from the dock or launch the tandem kayak into Pennekamp’s trails. Dock your boat (up to 25’ - no jet skis) and enjoy fishing, diving, or simply unwinding with a good book. This cozy retreat has everything you need — just bring your flip flops! No indoor smoking. No pets.

Guest favourite

Houseboat in Marathon

4.89 out of 5 average rating, 123 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Guest favourite

Home in Marathon

4.95 out of 5 average rating, 139 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you. Very Short Walking distance to Sweet Savannah's Ice Cream and Sweets Parlor

Guest favourite

Tiny home in Key Largo

4.88 out of 5 average rating, 187 reviews

Modern beach tiny house/Tiki hut/ boat dock 20ft

Modern beach 'Tiny House" cottage on Canal in key largo. Great location for boaters, fisherman and includes 20ft private dock. Great area to kayak, paddle board or fish. Private Tiki hut just steps from the water. Two kayak's included for your use. This is great community which includes private ramp and associotion pool for homeowners. Very close to private beaches only accessible by boat. Well behaved pets allowed

Top guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 129 reviews

Paradise found!Key Colony Beach,Cabana Club.

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!

Superhost

Home in Key Largo

4.87 out of 5 average rating, 113 reviews

villa hermosa

This home isn’t just a place to stay—it’s a place to create memories. So, come and enjoy everything Key Largo has to offer, and let this unique home be the perfect backdrop for your vacation. We can’t wait to welcome you and help make your time here unforgettable. Your comfort and satisfaction are our top priority, and we’re always available to assist with anything you need during your stay.