Holiday rentals with a kayak in Cudjoe Key

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Popular amenities for Cudjoe Key kayak rentals

Holiday House Rentals with a Kayak

Guest favourite
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.
Guest favourite
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars3 months ago
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars2 weeks ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Guest favourite
Home in Islamorada
5 out of 5 average rating, 18 reviews

Pristine pool front home w/ocean views Anglers 148

LindsayRating, 5 stars5 months ago
We recently had the pleasure of staying at this amazing beachfront house, and I can confidently say it exceeded all of my expectations! The location is simply perfect—just steps away from the water ideal for morning walks or sunrise views. The property itself is comfortable, with stylish and easy interiors that make it feel like a home away from home. The highlight was the pool—perfectly maintained and surrounded by lush greenery, offering a peaceful oasis to relax in when you want a break from the ocean. Whether you’re lounging by the pool with a book or enjoying a refreshing swim, it’s a great place to unwind. The host was also incredibly welcoming and provided thoughtful touches, from local recommendations to ensuring we had everything we needed for a great stay. I highly recommend this property for anyone looking to enjoy a relaxing beach getaway with the added luxury of a pool. Can’t wait to return!
Superhost
Home in Marathon
4.85 out of 5 average rating, 26 reviews

Dock Pool Ramp Jacuzzi Ocean Views Kayaks

WillRating, 5 stars1 month ago
This stay was the perfect vacation I was looking forward to, I stayed 7 days at this water front property with a great balcony to enjoy evenings and a boat ramp to launch the boats in the back yard along with the pool to keep us cool. Plenty of room for our trucks and trailers, the inside of the home was comfortable and relaxing. Was truly a great vacation Thank you
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

JohnRating, 5 stars10 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.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars2 weeks ago
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.
Guest favourite
Home in Marathon
5 out of 5 average rating, 22 reviews

Spacious lux home, private pool/spa, 80' dock

HeatherRating, 5 stars1 month ago
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!

Cottages with a kayak

Cottage in Cudjoe Key
4.82 out of 5 average rating, 98 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 favourite
Cottage in Islamorada
4.96 out of 5 average rating, 85 reviews

Islamorada bungalow 2 bed & pool

AmandaRating, 5 stars5 days ago
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!
Superhost
Cottage in Cudjoe Key
4.71 out of 5 average rating, 152 reviews

Calypso Cottage

JenniferRating, 5 stars2 weeks ago
Everything was perfect! I loved the screened in front porch! We spent a lot of time out there and the back was so peaceful for watching the sun come up with my morning cup of coffee. The staff at the resort were super friendly and helpful and I notice security was constantly driving around which made it feel safe and taken care of. Everyone at the resort looked so happy and relaxed! The pool!!! I didn’t want to leave and it has great hours! We were able to explore the area and still had time to go swimming at the pool…under the stars! It was a wonderful experience. Plan to some time go back and plan the whole trip staying there!
Guest favourite
Cottage in Marathon
4.97 out of 5 average rating, 35 reviews

Catch n' Relax Canalfront Cottage in Marathon

StefaniRating, 5 stars4 days 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!
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

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

MatthewRating, 5 stars1 month 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 Islamorada

Cottage on Bayfront Estate – Pool, Beach, & Dock

Quick stats about holiday rentals with a kayak in Cudjoe Key

  • Total rentals

    50 properties

  • Nightly prices starting at

    $246 AUD before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

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