
Vacation rentals with a kayak in Vaca Key
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Top-rated kayak rentals in Vaca Key
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House rentals with a kayak
Superhost

Home in Marathon
4.75 out of 5 average rating, 24 reviewsSunset Views, Pool and Dock
JamesRating, 5 stars2 weeks ago
We stayed at Frank’s place for two weeks and had an absolutely amazing time! The house was spotless, well-equipped, and super practical for our two energetic little ones. The pool and hot tub were perfect. We made the most of every sunset soaking in the hot tub, followed by peaceful late-night floats in the pool under clear, starry skies. We fished off the jetty most days and caught barracuda, mangrove snapper, plenty of sharks—and the neighbors even hooked a tarpon and landed a grouper! The kids loved snorkeling right off the dock, spotting rays, turtles, and loads of colorful fish. We missed the manatees when they came by one morning, but luckily caught up with them later while kayaking through the mangroves. Huge thanks to Frank for being such a fantastic host. One day we had a small issue with the pool, and his team showed up in under 10—absolutely amazing service. We truly didn’t want to leave and would come back in a heartbeat. Highly recommended!
Superhost

Home in Marathon
4.81 out of 5 average rating, 36 reviewsLuxury Waterfront Retreat with Dockage & Pool
KathrynRating, 5 stars4 days ago
We had a wonderful family vacation at Naomi’s place. The place was perfect for our family of 4. There was so much to do to keep our active family busy. The house was well stocked with everything you may need for meals. Host was very responsive and helpful throughout our stay. We rented a boat and the dock was perfect for storing. We are looking forward to staying here again on our next visit to the keys!
Superhost

Home in Marathon
5 out of 5 average rating, 3 reviewsWaterfront Oasis3/2 Direct Ocean
JohnRating, 5 stars9 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
4.86 out of 5 average rating, 7 reviewsDolfan Oceanfront Cottage Direct oceanfront with 5
ShawnRating, 5 stars15 months ago
This place was great. We close our business down every year for a week so staff can get away and every year some join us for a getaway. This year we came here, the Dolfan house was awesome. The view was amazing and having a boat dock to park the rental boat made it all the better. Idaho’s # 1 steakhouse (Wolf Lodge Steakhouse) will be back next year. Thank You
Guest favorite

Home in Key Largo
4.83 out of 5 average rating, 60 reviewsDeckhouse
OkyoRating, 5 stars1 month ago
Absolutely amazing! Tanya’s Airbnb was the perfect venue for our wedding. The space was stunning, beautifully maintained, and created the most magical atmosphere for our special day. Tanya and Lana were incredible hosts—responsive, accommodating, and truly went above and beyond to make sure everything was perfect. Our guests couldn’t stop raving about the beautiful setting and how comfortable the stay was. If you’re looking for a dreamy location with a fantastic host, this is it! Highly recommend! Let me know if you’d like any tweaks!
Top guest favorite

Home in Key Largo
4.94 out of 5 average rating, 16 reviewsKey Largo Village getaway
WestonRating, 5 stars1 month ago
If you are looking for a place to stay in the Keys, look no further. To start things off, Jenn is the best host you can ask for!! She was extremely responsive and incredibly sweet throughout the whole stay. She would always check in on us at the perfect times and really helped us feel right at home. Best experience I have ever had with a host!! As for the AirBnB itself, it was absolutely perfect for what we were looking for. It is tucked in a private family-friendly neighborhood that does a good job of drowning out any noise from the roads. It was exceptionally clean when we arrived and the amenities were fantastic. Really felt like a home away from home. The location was also very convenient and made our day trips to Miami and Key West a cinch. It is also near lots of amazing local beaches, snorkeling and kayaking spots, and restaurants. We will definitely be staying with Jenn again anytime we are in the area!!
Guest favorite

Home in Key Colony Beach
4.87 out of 5 average rating, 15 reviewsFun in the Sun!
BrentRating, 5 stars1 month ago
Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.
Guest favorite

Home in Marathon
4.88 out of 5 average rating, 24 reviewsGolf Coast Oasis
AmandaRating, 5 stars1 week ago
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!
Cottage rentals with a kayak
Guest favorite

Cottage in Islamorada
4.96 out of 5 average rating, 80 reviewsIslamorada bungalow 2 bed & pool
MoiraRating, 5 stars2 weeks ago
Very clean and hosts are very responsive. Couldn't find the toaster that was listed. Nice to have beach towels to use for the pool located next door or when going to the beach. Enjoyed having a cooler, beach chairs and umbrella to use for a beach outing. Loved the backyard with a fire pit and Adirondack chairs however the highway runs right behind it and it was a bit noisy. The pool next door was very clean and relaxing. We enjoyed our stay and the recommendations for restaurants and things to do in the area.

Cottage in Key Largo
4.75 out of 5 average rating, 12 reviews1 Bedroom Home in Key Largo
CandaceRating, 5 stars1 week ago
Our stay was truly relaxing and worry free. We brought our dog with us which was nice since the place was very dog friendly! Checking in/out was very easy and we felt very safe. The thing I appreciated the most about our stay was on incredibly bug free the property was, especially for being right on the water!
Top guest favorite

Cottage in Marathon
4.97 out of 5 average rating, 32 reviewsCatch n' Relax Canalfront Cottage in Marathon
SandyRating, 5 stars1 month ago
We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!

Cottage in Key Largo
4.67 out of 5 average rating, 12 reviewsWater View House in Key Largo
HannahRating, 5 stars2 weeks ago
This property was one of the best stays I’ve ever had with air bnb! Beautiful views from the windows of the air bnb, and the property is just steps away from the water. The beach area is small but was quiet, peaceful, and so relaxing. This property faces the sunset side of the keys, we watched the most beautiful sunsets over the water here. There was also some marine life in the water, we saw a manatee pass us just about 10 feet away! We really enjoyed using the kayaks, and it was helpful this air bnb had a full kitchen to stay in and eat for some meals. The tiny house itself was very clean. Good location with very short drives to restaurants and activities. We would definitely stay here again in the future!

Cottage in Islamorada
4.75 out of 5 average rating, 175 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
JaceyRating, 5 stars3 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
4.57 out of 5 average rating, 703 reviewsCottage Sunroom Waterfront Retreat 2 ppl
SophieRating, 5 stars1 week ago
We had a very relaxing stay at Joyce and Leslie’s wonderful home. The garden overlooking the water is really such a gem. They are both so friendly and accommodating. This was a much better value for money option than the local hotels and very peaceful. We met some fun other travellers staying there too and shared their birthday with them and Joyce and Leslie - Joyce’s Rum Cake was superb!

Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviewsLuxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
MatthewRating, 5 stars2 weeks 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!
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