Vacation rentals with a kayak in Cudjoe Key

Find and book unique kayak rentals on Airbnb

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Popular amenities for Cudjoe Key kayak rentals

House rentals with a kayak

Guest favourite
Home in Marathon
4.95 out of 5 average rating, 132 reviews

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

JenniferRating, 5 stars1 week ago
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!
Superhost
Home in Marathon
4.8 out of 5 average rating, 35 reviews

Luxury Waterfront Retreat with Dockage & Pool

SharonRating, 5 stars3 weeks ago
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!
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

JohnRating, 5 stars9 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.
Superhost
Home in Cudjoe Key
4.81 out of 5 average rating, 21 reviews

Keys Time #437 - Cudjoe Key, Oceanfront Community

FernandaRating, 5 stars2 days ago
We love the hosting! It was an amazing moment together with my family 🩵✨ The cleanliness was spectacular, besides the location! We’ll be back for sure
Guest favourite
Home in Marathon
4.94 out of 5 average rating, 32 reviews

Waterfront w/pool and hot tub

ErinRating, 5 stars1 month ago
We had a great time at this location. They had everything we needed and Key Colony is a perfect spot to vacation.
Guest favourite
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

JessicaRating, 5 stars1 month ago
If you are looking for a relaxing and peaceful location, this is the place! John was so helpful! The place was exactly as described. Our family felt right at home and enjoyed being away from the busyness of larger keys! Close to Key West and some amazing restaurants!
Guest favourite
Home in Key Colony Beach
4.87 out of 5 average rating, 15 reviews

Fun in the Sun!

BrentRating, 5 stars1 month ago
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.
Guest favourite
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars3 days ago
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!

Cottage rentals with a kayak

Cottage in Cudjoe Key
4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars7 months ago
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
Guest favourite
Cottage in Islamorada
4.96 out of 5 average rating, 79 reviews

Islamorada bungalow 2 bed & pool

KatieRating, 5 stars1 week ago
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
Superhost
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso Cottage

CourtneyRating, 5 stars2 weeks ago
Place was exactly like described, super quaint and had a great homey cottage feel. Neighbors were all super friendly as well. We really enjoyed being able to sit outside on the canal and enjoy our breakfast/dinner as well as playing any games. Would highly recommend this place, not far from key west a matter of 35-45 min depending on traffic
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviews

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

DawnRating, 5 stars12 months ago
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!
Superhost
Cottage in Cudjoe Key
New place to stay

Ocean Breeze at Venture Out 537

Quick stats about vacation rentals with a kayak in Cudjoe Key

  • Total rentals

    50 properties

  • Nightly prices starting at

    $221 CAD 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