
Vacation rentals with a kayak in Islamorada
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Top-rated kayak rentals in Islamorada
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House rentals with a kayak

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

Waterfront Escape -VACA-23-408
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.

Paradise found!Key Colony Beach,Cabana Club.
We had a great week at Kari's place. We were blown away by the view from the terrace. The apartment was well appointed and had everything we needed. The use of the nearby Cabana club was a real bonus. Colony Key is about an hour from Key West, so it was well located for all sorts of activities. Would love to return one day. Thanks Kari. Colin & Lynne Moore. Buckinghamshire, UK

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didnât work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryanâs place again in the future!

Waterfront Oasis w/Private Pool-Dockage-Beach
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.

Sunset Views, Pool and Dock
Thank you Frank for a great place to stay! Close to restaurants, quite neighborhood, nice pool, a dock to swim and fish from, and beautiful sunsets. We had everything we needed.

Waterfront Oasis3/2 Direct Ocean
Beautiful views and great spaces! Weâve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldnât get enough of all the beautiful views from sunrise to sunset whether it was on the porch, in the pool, or out by the Tiki Hut. Every bedroom has water views as well. Boat access was an easy out to snorkeling, diving, fishing, or whatever you like to do. There are two kayaks for use, which made for some nice outings to explore the immediate area. The kitchen had everything needed for cooking, and even had an extra under-the-counter ice machine. We had a great time here, and would stay again. Thank you to the owners for sharing your property.

Key Largo Waterfront Home with Tiki & Boat Dock
This is the perfect location for us, we have a small flats boat and thereâs great fishing in the area. The weather was not great but were able to find areas to fish sheltered from the wind. When not fishing, hanging out on the dock with Princess, watching the manatees and having a cold drink was absolute paradise. Penny is very responsive and was available anytime needed. This was our second time staying at this location and already talking about booking a longer stay next year.
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool
We had a blast at Yasmin and Joe's amazing cottage in the Keys! Perfect size for two couples (or a small family). When we arrived the place was pristine and exceeded our expectations from the photos. If you have a boat, being able to access the community's private ramp is a huge perk, and launching/retrieving the boat was a breeze. 10/10 and we'll be back. Thanks for sharing your property!

Ocean Breeze at Venture Out 537
I had a wonderful stay at this Airbnb! The home was perfect for our occasionâjust as advertised, and even more charming in person. The vibrant and inviting colors gave the space a warm, welcoming feel. There was a slight delay with check-in, but our host, John, responded quickly and resolved the issue right away, which we really appreciated. We also took full advantage of the amenities, which added to the overall experience. Everything was clean, comfortable, and well thought out. I would definitely stay here again and highly recommend it to others!

Catch n' Relax Canalfront Cottage in Marathon
We have three boys and they LOVED being able to fish anytime they wanted. We caught over 12 species of fish from the back dock. The kayaks were very handy! We just rented two more and We loved getting out in the mornings for a family kayaking adventure and the boys fished any chance they got. They even caught a nurse shark! The house was clean and well decorated. There were handy items such as sunscreen and life vests. It was a great place for a family of five.

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
We brought another couple with us. Had a relaxing enjoyable time. Felt like home. Definitely be back. Thank you

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!

OCEANIA... water front cottage retreat ~
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my sonâs large pickup. Curious as to what that fee actually pays for. We would definitely stay again.

THE PARADISE
We were there because we was celebrating my husbandâs birthday and our wedding anniversary . It was a great place to stay highly recommend it. Quiet and comfortable atmosphere for a great long weekend. Luis Alberto and his wife very attentive. It makes us feel like weâre around family.. canât wait to come back again. Our favorite place to go for now on.
Quick stats about vacation rentals with a kayak in Islamorada
Total rentals
110 properties
Nightly prices starting at
G$25,083Â GYD before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
80 properties have a pool
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- Sombrero Beach
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