Holiday rentals with a kayak in Windley Key

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Popular amenities for Windley 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 Key Colony Beach
4.98 out of 5 average rating, 124 reviews

Paradise found!Key Colony Beach,Cabana Club.

ColinRating, 5 stars1 week 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
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
4.76 out of 5 average rating, 25 reviews

Sunset Views, Pool and Dock

GregRating, 5 stars1 month ago
Thank you Frank for a great place to stay! Close to restaurants, quite neighborhood, nice pool, a dock to swim and fish from, and beautiful sunsets. We had everything we needed.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars2 weeks ago
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.
Top Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 88 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

MattRating, 5 stars1 week ago
Stu's house was perfect! Very comfortable, peaceful, clean and close to lots of activities. We enjoyed the outside areas down by the dock as well as the upstairs screened porch. Being right on a canal with easy access to great areas to explore with the included kayaks made our trip more enjoyable. We hope to return again soon!
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.
Top Guest favourite
Home in Islamorada
5 out of 5 average rating, 5 reviews

Anglers Haven- 2 bed 2 bath home in Islamorada

BenRating, 5 stars5 months ago
Spent the week of Christmas. Great location. Perfect for our family.

Cottages with a kayak

Guest favourite
Cottage in Islamorada
4.96 out of 5 average rating, 85 reviews

Islamorada bungalow 2 bed & pool

AmandaRating, 5 stars6 days ago
The hosts were very responsive and accommodating to our needs. The pool was great and the place was pristine!
Cottage in Key Largo
4.75 out of 5 average rating, 16 reviews

1 Bedroom Home in Key Largo

HollyRating, 5 stars1 week ago
This was such a fun stay! The little beach cottages were so cute. The bedroom is rather tight and the loft is designed for children size guests, but we didn't mind. The kitchen had everything we needed, the dock and beach area were where we spent most of our time outside of wedding festivities, the grill and firepits were a nice touch too. The guy working the whole time we were there was great, he was great with communication and super friendly. Hard worker! I will say we did not get the house from the post- but only the picture of the outside. Which was totally fine, the inside was exactly the same. Another guest in our party had the same experience but didn't get a loft- but if you are like them and didn't need a loft those cabins were actually nicer. I read other reviews stating they didn't get the cabin they requested, but it seemed like there were only a few different variations of exactly the same model with different external design. I'd do it all again!
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.
Top Guest favourite
Cottage in Key Largo
5 out of 5 average rating, 13 reviews

Kampground Paradise w/Kayaks, Heated Pool & Marina

CheriRating, 5 stars1 week ago
Fantastic place to vacation! Key Largo Kampground is a very cute and fun place to stay. We swam in the pool every day, got to see manatees at the docks, played on the playground - it was great! The house is right next to the office and a lot of amenities, so the location was excellent. Obviously it's a tiny house, but we found for our family of 4 that there was plenty of room, and we felt more than comfortable. I was originally concerned that the loft might get hot, but the A/C worked fantastic, and it was just a really easy, comfortable stay! There's also a neighborhood cat that decided we were its people, so that made for a fun little addition to our vacation! I highly recommend staying here, and we plan on coming back!
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!
Private room in Key Largo
4.58 out of 5 average rating, 715 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

TracyRating, 5 stars2 weeks ago
This place is beautiful with old Florida charm. Will be back!
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!
Guest favourite
Cottage in Key Largo
4.91 out of 5 average rating, 85 reviews

THE PARADISE

MiaRating, 5 stars1 week ago
Luis was amazing! So responsive and accommodating. The neighbors were fantastic! We’re from California and will definitely be coming back to visit Luis’s place and our new Florida friends in the neighborhood! Gracias Luis!

Destinations to explore

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