Vacation rentals with a kayak in Islamorada

Find and book unique kayak rentals on Airbnb

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Popular amenities for Islamorada kayak rentals

House rentals with a kayak

Top guest favorite
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks ago
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!!
Guest favorite
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars1 week ago
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.
Top guest favorite
Home in Key Colony Beach
4.98 out of 5 average rating, 124 reviews

Paradise found!Key Colony Beach,Cabana Club.

ColinRating, 5 stars1 week ago
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
Guest favorite
Home in Marathon
4.95 out of 5 average rating, 136 reviews

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

TashaRating, 5 stars1 week ago
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 didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!
Top guest favorite
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars5 months ago
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.
Superhost
Home in Marathon
4.76 out of 5 average rating, 25 reviews

Sunset Views, Pool and Dock

GregRating, 5 stars1 month ago
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.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

JohnRating, 5 stars11 months ago
Beautiful views and great spaces! We’ve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldn’t 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.
Top guest favorite
Home in Key Largo
4.97 out of 5 average rating, 161 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

MattRating, 5 stars1 week ago
This is the perfect location for us, we have a small flats boat and there’s 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

Guest favorite
Cottage in Islamorada
4.97 out of 5 average rating, 86 reviews

Islamorada bungalow 2 bed & pool

DavidRating, 5 stars2 weeks ago
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!
Superhost
Cottage in Cudjoe Key
4.8 out of 5 average rating, 5 reviews

Ocean Breeze at Venture Out 537

MelissaRating, 5 stars3 weeks ago
I had a wonderful stay at this Airbnb! The home was perfect for our occasion—just 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!
Guest favorite
Cottage in Marathon
4.97 out of 5 average rating, 36 reviews

Catch n' Relax Canalfront Cottage in Marathon

StefaniRating, 5 stars1 week ago
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.
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars4 months ago
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!
Guest favorite
Cottage in Cudjoe Key
4.93 out of 5 average rating, 129 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

DonnaRating, 5 stars1 month ago
We brought another couple with us. Had a relaxing enjoyable time. Felt like home. Definitely be back. Thank you
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

MatthewRating, 5 stars2 months ago
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!
Cottage in Cudjoe Key
4.81 out of 5 average rating, 99 reviews

OCEANIA... water front cottage retreat ~

DeniseRating, 5 stars1 month ago
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 son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
Guest favorite
Cottage in Key Largo
4.91 out of 5 average rating, 86 reviews

THE PARADISE

JessicaRating, 5 stars3 days ago
We were there because we was celebrating my husband‘s 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 we’re around family.. can’t 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$25,083 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Rentals with a kayak