
Vacation rentals with a kayak in Islamorada
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Top-rated kayak rentals in Islamorada
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House rentals with a kayak

Waterfront Escape -VACA-23-408
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.

Waterfront with Boat Lift/Kayaks and Hot Tub
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!!

Paradise found!Key Colony Beach,Cabana Club.
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

Dock Pool Ramp Jacuzzi Ocean Views Kayaks
This stay was the perfect vacation I was looking forward to, I stayed 7 days at this water front property with a great balcony to enjoy evenings and a boat ramp to launch the boats in the back yard along with the pool to keep us cool. Plenty of room for our trucks and trailers, the inside of the home was comfortable and relaxing. Was truly a great vacation Thank you

Sombrero beach oasis, great location, many amenities
Incredible for a family vacation. 🏝️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!

Waterfront Oasis w/Private Pool-Dockage-Beach
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.

Key Largo Waterfront Home with Tiki & Boat Dock
This is the perfect location for us, we have a small flats boat and there’s great fishing in the area. The weather was not great but were able to find areas to fish sheltered from the wind. When not fishing, hanging out on the dock with Princess, watching the manatees and having a cold drink was absolute paradise. Penny is very responsive and was available anytime needed. This was our second time staying at this location and already talking about booking a longer stay next year.

Spacious lux home, private pool/spa, 80' dock
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!
Cottage rentals with a kayak

Islamorada bungalow 2 bed & pool
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!

1 Bedroom Home in Key Largo
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!

Catch n' Relax Canalfront Cottage in Marathon
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.

Kampground Paradise w/Kayaks, Heated Pool & Marina
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!

Tropical House By The Shore at Largo Resort
Great stay!!

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
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 Sunroom Waterfront Retreat 2 ppl
This place is beautiful with old Florida charm. Will be back!

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
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 vacation rentals with a kayak in Islamorada
Total rentals
110 properties
Nightly prices starting at
G$25,106 GYD before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
80 properties have a pool
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
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- Cannon Beach
- Conch Key
- Calusa Beach & Loggerhead Beach
- Theater of the Sea
- Everglades Alligator Farm
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- EAA Air Museum
- Long Beach
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- Far Beach
- Monkey Jungle
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
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