
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

Pristine pool front home w/ocean views Anglers 148
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!

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

Waterfront Miami Oasis w/ Kayaks | Heated Pool
AMAZING Host and location I recommend this to anybody staying in the area . Beautiful clean home with plenty of things to do. The pictures do no justice for how amazing this property looks. BOOK THIS BEAUTIFUL PLACE FOR YOUR NEXT GETAWAY

Keys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More
We had a fun stay in Key Largo at Gabriel/Stu's place. Plenty of space for 5 adults, and the screened in areas were a nice bonus! There was a slight snafu with the AC, but Stu was very responsive and had it taken care of quickly. We did see a couple manatees cruise through the canal one evening. Overall, everything was clean and enjoyable. Also important to note is, although some of the neighbors had get togethers with loud music, we couldnt hear any of it inside the house. I really can't speak enough to Stu's hospitality and responsiveness!

Large Waterfront Home, w/Efficiency, Pool, Kayaks
Stu's house was perfect! Very comfortable, peaceful, clean and close to lots of activities. We enjoyed the outside areas down by the dock as well as the upstairs screened porch. Being right on a canal with easy access to great areas to explore with the included kayaks made our trip more enjoyable. We hope to return again soon!

Waterfront Home 37.5-ft dock, Cabana Club Included
We were very comfortable at the home during our week stay. Great place to stay if you need room to park a boat trailer. Quiet very nice safe neighborhood.

Luxury Boating Paradise+Pool+Sailing Kayaks
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!

WatersEdge, TropicalHideaway, FLL, MIA, Port, Pool
Absolutely the best stay here! Lara was the best and so friendly! I will definitely look into staying in this Airbnb again!!!
Cottage rentals with a kayak

Cozy Tropical Cottage. Your new Happy Place!
Das Airbnb von Toni liegt in einer sehr ruhigen, sicheren Umgebung und ist von viel Grün umringt. Das Einchecken war sehr einfach und schnell. Die Räume sind alle sehr gemütlich eingerichtet und sehr sauber. Die Küche ist mit allem ausgestattet was man so braucht um sich ein leckeres Essen zuzubereiten. Über den Willkommensgruß haben wir uns sehr gefreut, auch über das Obst. Das Bett ist sehr bequem, deswegen haben wir wunderbar geschlafen. Das Bad war mit vielen Handtüchern ausgestattet. An allen Fenstern gab es Gage, so hatten wir auch keine lästigen Mücken im Haus. Bei Fragen bekamen wir eine schnelle Antwort. Dieses Airbnb kann man 100% weiterempfehlen und wir würden hier jederzeit gerne wieder übernachten. Vielen Dank.

Islamorada bungalow 2 bed & pool
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!

1 Bedroom Home in Key Largo
This was such a fun stay! The little beach cottages were so cute. The bedroom is rather tight and the loft is designed for children size guests, but we didn't mind. The kitchen had everything we needed, the dock and beach area were where we spent most of our time outside of wedding festivities, the grill and firepits were a nice touch too. The guy working the whole time we were there was great, he was great with communication and super friendly. Hard worker! I will say we did not get the house from the post- but only the picture of the outside. Which was totally fine, the inside was exactly the same. Another guest in our party had the same experience but didn't get a loft- but if you are like them and didn't need a loft those cabins were actually nicer. I read other reviews stating they didn't get the cabin they requested, but it seemed like there were only a few different variations of exactly the same model with different external design. I'd do it all again!

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!

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
Luis was amazing! So responsive and accommodating. The neighbors were fantastic! We’re from California and will definitely be coming back to visit Luis’s place and our new Florida friends in the neighborhood! Gracias Luis!
Quick stats about vacation rentals with a kayak in Key Largo
Total rentals
270 properties
Nightly prices starting at
G$20,915 GYD 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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- Bayfront Park
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
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