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Holiday rentals with a kayak in Big Pine Key

Find and book unique kayak rentals on Airbnb

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Popular amenities for kayak rentals in Big Pine Key

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 stars3 days 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 stars2 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.
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 68 reviews

Sombrero beach oasis, great location, many amenities

KendallRating, 5 stars2 weeks ago
Incredible for a family vacation. šŸļø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!
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 135 reviews

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

AlyssaRating, 5 stars2 weeks ago
We all had a great time and the house was gorgeous! The house had everything we needed for a pool day or a fishing day. The location is great and has everything you need around. The host even sent key lime pies from Sweet Savannah’s (walking distance) as a sweet gesture after needing a few people to stop by to fix something outside. We can’t wait to stay again!
Superhost
Home in Cudjoe Key
4.62 out of 5 average rating, 165 reviews

Ocean Front Home in Great Location

MichaelRating, 5 stars1 month ago
Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, I’d say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!
Top guest favourite
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars5 months ago
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
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.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

*NEW!*Paradise Palms~Dock~Pool~Kayaks Grill~View!

NuciaRating, 5 stars1 month ago
We had a wonderful family vacation getaway at Katie and Cody’s place. The house was very clean, and the location is great as well with accessibility to food, Publix, and great beaches. Our favorite aspect of the house was the small pool. Our teenagers played in it endlessly, and when they were gone we enjoyed relaxing on the pool floats. Communication with Katie was top notch. She always responded quickly and had great follow through with any issues we had. they definitely go above and beyond to provide resources of fun activities and resteraunts in the area. We would definitely stay here again!

Cottage rentals 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, 84 reviews

Islamorada bungalow 2 bed & pool

LynnRating, 5 stars2 weeks ago
Such a warm, quaint place. Clean, right next to the pool and close to nearby restaurants, activities and much more. Loved it.
Superhost
Cottage in Cudjoe Key
4.71 out of 5 average rating, 152 reviews

Calypso Cottage

JenniferRating, 5 stars1 week 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!
Top guest favourite
Cottage in Marathon
4.97 out of 5 average rating, 34 reviews

Catch n' Relax Canalfront Cottage in Marathon

DeborahRating, 5 stars1 week ago
We really enjoyed our stay at Wendy's place! It was clean, comfortable, and had everything we needed for our stay. We enjoyed riding the bikes to Seven Mile Bridge and exploring with the kayaks. Would definitely recommend it!
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 Big Pine Key

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹10,295 before taxes and fees

  • Total number of reviews

    240 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

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