
Vacation rentals with a kayak in Key West
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Top-rated kayak rentals in Key West
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House rentals with a kayak

Discount Available! 100' Dock, Lots of Amenities!
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.

Private Pool, Spa, Game Room, Dock & Tiki Hut!
Upon our check-in, there was a crew putting in new cabinets and knobs who were there for 1.5 hours after we arrived. Not the greatest way to start off the vacation but we know these things can sometimes be out of your control. What I appreciated the most was how quickly they remedied the hot pool situation. When we got there, the pool looked so wonderful to cool off in but to our disappointment the water was 94 degrees. We notified Bert and he had the pool cooled off by the next morning. Overall the house was clean and the location was perfect. The house also stayed nice and cool with the extra units in some of the rooms. Most beds were comfortable, with the exception of a very wobbly bunk bed. The pluming was a little old and probably could use some new pluming fixtures but that wasnt a big deal once we learned how to work the knobs. We were also able to add a dog to the reservation last min so we appreciated the flexibility. Overall, was a nice experience.

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

Sombrero beach oasis, great location, many amenities
Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!

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 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!

Waterfront FL Keys Cottage @ Venture Out
This was a great place to stay to experience the beauty of the Florida Keys. The pool, hot tub, and amenities are very well worth it, and the location and proximity to Key West is a huge plus as well. Very relaxing and accommodating!

Golf Coast Oasis
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!

Waterfront Heated Pool 120 ft Boat Dock
A Hidden Gem – Perfection in Every Way! Truly! This was, one of the best Airbnbs we have been to in Marathon! We have traveled down for many years and could not ask for a better place!!! From the moment we arrived, everything was absolutely perfect. The space was spotless, it slept 8 of us comfortably! Stocked with every single thing we could need! Location itself was Unbeatable! Peaceful, picturesque, and close to everything, yet somehow still felt like our own private escape! The dock cutting board and easy water hose worked perfect for any catch! The wrap around deck was the biggest hit! Seeing manatees and Tarpon sightings really made my kids day! It truly was magical experience! The pool to cool off and the mini splits in each room without it being manually controlled was the ultimate! Milton was phenomenal to communicate with! You can tell he genuinely cares about his guests♥️. Our family has already booked for next year and we highly recommend!
Cottage rentals with a kayak

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 son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.

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!

Calypso Cottage
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!

Ocean Breeze at Venture Out 537
We are first timers to the keys and were not only on our honeymoon, but also our first vacation away alone for a week. We could not have been happier. We loved every minute of our stay both on the property and in the entire area. John communicated everything clearly from the booking and we had no reasons to contact him.

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!

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!

Cottage on Bayfront Estate – Pool, Beach, & Dock
Quick stats about vacation rentals with a kayak in Key West
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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