Holiday rentals with a kayak in Summerland Key

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Popular amenities for Summerland Key kayak rentals

Holiday House Rentals with a Kayak

Superhost
Home in Marathon
4.89 out of 5 average rating, 18 reviews

Salty kisses beach house

AnaRating, 5 stars1 month ago
Had a wonderful time at Salty Kisses. The area was beautiful and we were able to relax with the stunning views of the backyard. The house had everything we needed in the kitchen, bedrooms, bathrooms, and even outside for entertainment. Lazaro was very attentive making sure everything was good. Neighborhood was quiet. We spent a lot of time in the pool, grilling, and out on the water which was easily accessible with the dock at the front of the house. The whole family was in love with the decorations of the house which were truly beautiful and making us feel right at home. Thank you Laz and Leslie!
Guest favourite
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars1 week 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, 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!!
Guest favourite
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars3 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
5 out of 5 average rating, 13 reviews

Private Pool, Spa, Game Room, Dock & Tiki Hut!

JodyRating, 5 stars1 week ago
Very nice and comfortable home. Super clean! ALL the appliances you could need in the kitchen! Many utensils which is imperative for a large group. Lots of seating inside and outside! Pool area secure and private. Very relaxing and beautiful! Plenty of towels/linens. Whatever we brought to Bert’s attention, he was very responsive with, and he very quickly remedied it! 5 star! Will definitely consider staying again!
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!
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

JohnRating, 5 stars11 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!

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.
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 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 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!

Quick stats about holiday rentals with a kayak in Summerland Key

  • Total rentals

    50 properties

  • Nightly prices starting at

    $266 NZD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

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