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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 Big Pine Key kayak rentals

Holiday House Rentals with a Kayak

Top Guest favourite
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars2 weeks ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 68 reviews

Sombrero beach oasis, great location, many amenities

KendallRating, 5 stars3 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, 136 reviews

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

TashaRating, 5 stars1 week ago
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!
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 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!
Superhost
Home in Marathon
4.85 out of 5 average rating, 26 reviews

Pelican Inn

JamesRating, 5 stars3 weeks ago
Karen’s place was amazing. Sitting on the deck and fishing was fun to do during the day and in the evenings when we wanted to relax. We were visited by manatees and saw some very cool fish in the canal. The location was perfect right in the middle of the keys with an hour to get to key west and key largo each direction. Local restaurants were bike riding distance. The house was clean and very nicely taken care of. Most of the local neighbors were nice or the people who owned the surrounding homes as vacation homes. Except for the guy who owns the house directly in front of Karen’s closest to the street, yellow house I believe, he had some rude things to say regarding us fishing but it’s not Karen’s fault the neighbor was a rude person, all the others were lovely. We enjoyed our stay so much and would love to return one day.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 52 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars3 weeks ago
The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

Cottages with a kayak

Cottage in Cudjoe Key
4.81 out of 5 average rating, 99 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, 85 reviews

Islamorada bungalow 2 bed & pool

AmandaRating, 5 stars1 week ago
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!
Superhost
Cottage in Cudjoe Key
4.71 out of 5 average rating, 152 reviews

Calypso Cottage

JenniferRating, 5 stars2 weeks 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!
Guest favourite
Cottage in Marathon
4.97 out of 5 average rating, 35 reviews

Catch n' Relax Canalfront Cottage in Marathon

StefaniRating, 5 stars5 days ago
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.
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

    $185Ā AUD 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