Holiday rentals with a kayak in Monroe County

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Popular amenities for Monroe County kayak rentals

Holiday 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 stars2 weeks 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.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars3 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.
Top Guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 124 reviews

Paradise found!Key Colony Beach,Cabana Club.

ColinRating, 5 stars2 weeks ago
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
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 136 reviews

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

TashaRating, 5 stars2 weeks 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.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 53 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

LoganRating, 5 stars4 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.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 76 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

SusanRating, 5 stars2 months ago
Our gals trip was wonderful. The pool, ping pong table, corn hole, kayaks, nice bikes, and paddle boards were great amenities to have. The home is located just a couple blocks from Sombrero Beach. All of the outdoor patio furniture was great quality. Nice appliances all around. The beds were very comfortable.
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 33 reviews

Waterfront FL Keys Cottage @ Venture Out

AlexRating, 5 stars1 week ago
Great space in a quiet and safe neighborhood. The place has everything you need and very useful and thoughtful touches and tips to enhance your trip.

Cottages with a kayak

Guest favourite
Cottage in Islamorada
4.97 out of 5 average rating, 86 reviews

Islamorada bungalow 2 bed & pool

DavidRating, 5 stars2 weeks ago
We had a blast at Yasmin and Joe's amazing cottage in the Keys! Perfect size for two couples (or a small family). When we arrived the place was pristine and exceeded our expectations from the photos. If you have a boat, being able to access the community's private ramp is a huge perk, and launching/retrieving the boat was a breeze. 10/10 and we'll be back. Thanks for sharing your property!
Superhost
Cottage in Cudjoe Key
4.83 out of 5 average rating, 6 reviews

Ocean Breeze at Venture Out 537

ChristopherRating, 5 stars3 weeks ago
We are first timers to the keys and were not only on our honeymoon, but also our first vacation away alone for a week. We could not have been happier. We loved every minute of our stay both on the property and in the entire area. John communicated everything clearly from the booking and we had no reasons to contact him.
Top Guest favourite
Cottage in Marathon
4.97 out of 5 average rating, 36 reviews

Catch n' Relax Canalfront Cottage in Marathon

StefaniRating, 5 stars1 week 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 Key Largo
4.4 out of 5 average rating, 5 reviews

Tropical House By The Shore at Largo Resort

ChristyRating, 5 stars12 months ago
Great stay!!
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 stars2 months 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 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 Key Largo
4.91 out of 5 average rating, 86 reviews

THE PARADISE

JessicaRating, 5 stars6 days ago
We were there because we was celebrating my husband‘s birthday and our wedding anniversary . It was a great place to stay highly recommend it. Quiet and comfortable atmosphere for a great long weekend. Luis Alberto and his wife very attentive. It makes us feel like we’re around family.. can’t wait to come back again. Our favorite place to go for now on.

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