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

Keys Home, Boat Slip + Golf Cart
This house was everything previous excellent reviews had indicated: beautiful home, clean, well equipped, and a great location to explore the Keys. Anthony was very responsive. The home had a luxury feel, but was affordable. All in all, highly recommended!

Sunset Views, Pool and Dock
We really liked the location. It was peaceful and private and a great neighborhood to walk around and to walk our dog. Yet, a short drive into Marathon for restaurants or any other needs. The house isn’t new but it was exactly as represented and it was perfect for us. Frank was very responsive. There were a couple of issues that he addressed immediately. It wasn’t his fault that because of the location, receiving repair parts can take some time. But Frank took care of our situations.

Luxury Waterfront Retreat with Dockage & Pool
We enjoyed our stay. The home was comfortable and very clean. It was nice to have a view of the water and a heated pool! The rooms were comfortable and accommodating for our family. Naomi was quick to respond when we had questions. I would stay here again! This spot was close to many restaurants, grocery stores, and right on bike paths!

Large Waterfront Home, w/Efficiency, Pool, Kayaks
We had everything we needed! Stu was helpful and responsive. We had a fantastic time and will be back in the future! Don’t miss a chance to stay here in Key Largo. Great location and loved keeping the boat behind the house. House is very clean and has all of the amenities you could possibly think of!! 10/10 recommend!

Dolfan Oceanfront Cottage Direct oceanfront with 5
This place was great. We close our business down every year for a week so staff can get away and every year some join us for a getaway. This year we came here, the Dolfan house was awesome. The view was amazing and having a boat dock to park the rental boat made it all the better. Idaho’s # 1 steakhouse (Wolf Lodge Steakhouse) will be back next year. Thank You

Deckhouse
Absolutely amazing! Tanya’s Airbnb was the perfect venue for our wedding. The space was stunning, beautifully maintained, and created the most magical atmosphere for our special day. Tanya and Lana were incredible hosts—responsive, accommodating, and truly went above and beyond to make sure everything was perfect. Our guests couldn’t stop raving about the beautiful setting and how comfortable the stay was. If you’re looking for a dreamy location with a fantastic host, this is it! Highly recommend! Let me know if you’d like any tweaks!

Fun in the Sun!
Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.

Golf Coast Oasis
We really enjoyed our week at Gulf Coast Oasis! The house was lovely, well-stocked, and great for our family of 5. We very VERY much enjoyed the pool and appreciated being able to heat it. Loved using the bikes and kayaks. Ate on the screened in porch. Madelyn was very helpful and responsive both in advance of and during our trip. Great stay! The only "negative" was the noise from the nearby airport -- not disruptive but worth noting.
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool
Beautifully decorated bungalow with everything you need for a relaxing holiday. We stayed with our two boys who loved the pool next door and the fire pit in the back garden. Great base for exploring Islamorada. Recommend watching the sunset and enjoying some great food at Papa Joes. Lovely responsive host

Catch n' Relax Canalfront Cottage in Marathon
We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!

Kampground Paradise w/Kayaks, Heated Pool & Marina
What an amazing stay!! The campground was so peaceful and tucked away from everyday reality. This trip was a much needed escape from our everyday life! The cottage was very new and clean and came with all the amenity’s needed to enjoy all the local beaches. The host was great and responded immediately with any questions we had. We will for sure be back again :)

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
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!

New 150 ft Dock/Private Swim Spa/Tiki/Outdoor Bar
This was one of our favorite Air BnB rentals. The house was easy to get to from the Miami Airport, but was far away from the hustle of Florida. The amenities at the house were extraordinary and appropriate. Michelle was in the oversized hot tub twice a day while I was out on the canoe exploring the mangroves and fishing alongside Manatees and Stingrays. The dock provided multiple locations to be in, or out of the sun to fish, read or take in some sun. I did all three at the same time! The fire pit was in the perfect spot where we cooked most of our dinners. If you are looking for a spot for a mellow time to get away from the Northern cold and snow to relax, this is the spot. Sean was more accommodating and proactive with his replies and suggestions than most. There is even a sign on the refrigerator with his cell phone noting that 'if you are not having a 5* vacation, call me, and if you are, call me to rebook'! From the attention to detail throughout, he meant it!!

Beautiful 3 bedroom cottage with private rooftop
I stayed at Jeff's place with 4 of my cousins, so 5 girls in the house. We were anticipating a trip just to hang out at a beach for a couple of days and this was a great place to do that. It was a great stay, we were close to the beach. Jeff had beach chairs ready for us and a wagon to pull them to the beach. It was like a half a block walk to the boardwalk and beach. We spent a lot of time walking the boardwalk, checking out the shops and eateries and enjoyed the beautiful sandy beach. Their is a nice bottom deck and top deck which we enjoyed coffee out there in the morning and playing cards later at night. We would definitely come back here or recommend this place. Jeff was very easy to reach out to and responded to texts very well. He even called us the morning we were checking out to make sure everything was OK. NOTE: There are towels in the bathrooms, but no wash cloths and no dish cloths (there is a sponge) and no dish towel. So next time I would pack each of those.

THE PARADISE
My husband and I stayed 3 nights and this place is so cute. Older tiny home with recent updates. Great location to be venture out and see Key Largo and it’s true .. the neighbors are so nice.
Quick stats about vacation rentals with a kayak in Key Largo
Total rentals
270 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
10K reviews
Family-friendly rentals
240 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
160 properties have a pool
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