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

Bay view and possible two family rental!
we had a wonderful time at Robert's place. Everything was as described. the island is a perfect getaway for anyone that wants to go on an adventure and get away from the hustle and bustle. The kitchen had everything you would need to cook, it was perfect! Everything was well thought of in this home. On a side note, golf carts need to be booked months in advance and are pretty pricey and we hoped to walk around the island but we're told upon checkin that was not allowed. we could only go to the beach and back to the property. You could walk along the beach though.

Summer House longboat key
We had a wonderful stay at Chris’s house on longboat key! The pool was so nice for the kids and us adults to swim and relax by. The house was very nice and the beds were very comfortable. There were plenty of towels, extra sheets, and the kitchen was very well stocked with pot and pans. We did find it easier to drive closer to the crosswalk to the beach and park before walking across the street to get to the beach access. The beach was very quiet and beautiful. We found so many shells and our kids loved doing evening swims at sunset! It’s a very quick drive to Anna Maria Island and St Armand’s Circle. We really enjoyed our stay.

Waterfront, Gulf Access, Dock, Heated Pool & Kayak
We had an amazing stay! The place was immaculately clean—honestly one of the cleanest Airbnbs we’ve ever stayed in. Everything was spotless and so well cared for, which made it feel extra comfortable and relaxing. It is well equipped with everything needed for a stay away from home. The highlight for us was the beautiful pool area and the stunning canal water views—such a peaceful setting, especially in the mornings and evenings. The area is safe and nice for morning and evening runs or walks as well. Merrill was super responsive and made everything easy from start to finish including voluntarily offering a late checkout to accomodate our flight schedule! We would definitely love to come back and highly recommend this lovely island retreat to anyone looking for a clean, scenic, and relaxing getaway! Ariani’s is the little Italian restaurant recommended in the hosts guidebook. Make sure to plan on dining there during your stay! Great choice!

3/2 Home w/ Sailboat Lot“A Fisherman’s Dream Home”
We loved our stay at 328 Morse! It was the perfect location and size for our family (visiting for a baseball tournament). Fishing from the dock was great fun, we caught a variety of fish on lures, worms and shiners. It was so nice to walk out the back door into the well maintained yard and throw a line in to see what was biting. The kayaks and tree swing were added bonuses. The kitchen is clean and well stocked and we enjoyed making meals at home when not eating out. Returning to the house after our adventures was a pleasure!

Waterfront Key West Style Home
beautiful home, pool and property

Apollo Beach Waterfront Amazing Pool Oasis
This property was perfect for our family vacation. The outdoor pool and view of the canal was wonderful- we saw dolphins and a manatee! The kids (age 10 and 12) loved the pool table, Jenga, and corn hole. The house was very clean, every amenity needed, and very comfortable. The hosts, Bacem and Caryn were extremely helpful, responsive, and friendly. The area is very convenient with lots to do. We explored St. Petersburg beach and Tampa Bay. Highly recommend this home!

Bungalow near the sea
Great place and great location!

Waterfront Family Getaway, Sleeps 14 , 9 Beds
Our stay was wonderful! The house was exactly as described, Viktoria and Vadim communicated early and often, giving us clear instructions and making sure we had everything we needed. The house was perfect for my family and was very clean. My son even left a personal item behind after we departed and Viktoria called me to say she found it and offered to mail it to us. Very very helpful! Would definitely recommend!
Cottage rentals with a kayak

Anna Maria Cottage w/Golf Cart
This was a great place to stay for the week, very clean and quiet. Good location to get to either side of the island and the beach. Having the golf cart and beach gear was very helpful! Lynda was a great host.

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike
If you are looking for a historic, old-school Florida home, this is it. The only reason it isn’t a perfect score is that the hurricane closed most of the shops that make Pass-a-Grille quaint. We were able to support a few local restaurants, and the local traffic was very light. We wouldn’t have changed our trip, but it would have been good to know. It seems like businesses are working hard to get back on their feet. Overall a good experience. I appreciate Lisa’s great responsiveness.

Last Minute-Villa Seafan-modern, pool, kayaks
This is a beautiful home. Well appointed and well maintained. Everything was spotless. I would stay here again in a heartbeat!! The host thought of almost everything. Kayaks, bicycles, pool towels, etc. My only recommendations for improvement would be facial tissues and fans for sleeping. That’s it! That’s all I could think of.

Good after Milton - Waterfall Pool! Beach! am
Very nice place to stay. Perfect location to the beaches and nice restaurants/hang out spots that were very close. Very quiet and peaceful. September is a quiet month - not lots of tourists. Lovely place that was clean and nicely decorated. My only issue was that the shower water never got above luke warm. I like hot showers. Otherwise, very nice place to stay. I would definitely recommend.

West Coast Island Retreat, Simply Adrift Cottage
We had a great time staying here! The home was beautiful with all the beach supplies one could want. As someone who drove their boat up, the dock had great cleat availability and we had no problems getting a spot. One of the easier places to dock at that I have stayed overnight. Home also has everything for cooking and good wifi for being on an island. Loved the vibe of LGI, watching the sunset, and exploring the surrounding islands. Would definitely stay again!

Captains Cottage
We had to wait about 30 min after arriving at check in time to get the access code, but other than that we enjoyed our stay very much!! The grill wasn’t working, and Tina sent the housekeeper over with a charcoal grill, charcoal, lighter fluid, and even a lighter. Her responses were timely and very helpful. We would definitely come back again 💚

Snail's Pace: On Canal, Kayaks & Dog Friendly
awesome place and people! super responsive and friendly - let us check in early even asking last minute. SUPER clean - like cleaner than most hotels i have been in. very comfortable and awesome place to stay. we had neighbors on the other side of the building and never heard them once, and there was construction right next door that you could not hear inside. amazing appliances that looked and worked like new. super amazing place and would definitely book here again.

Sunset Cottage: Lake Front
Fantastic home with everything you need to have a wonderful vacation. The property was clean and well maintained. The outdoor space was amazing. We can't wait to return.
Cabin rentals with a kayak

Unique loft experience for motorcycle enthusiasts
Awesome and fun place to stay, especially if you're big into bikes or drag racing! Would recommend!

Waterfront Retreat- w/Kayaks & Peace River access
As I indicated in the earlier part of the review, the location, grounds, and cabins were amazing. We had a large group of canoers stay in what we called the lodge - with 5 bedrooms and 2 bunk rooms. Though there are only 2 showers in the same bathroom for such a large number - we made it work. Megan and Marc left each cabin (we rented the lodge and 2 tiny cabins) with a half dozen or more organic, home raised fresh duck and chicken eggs. Nice touch! Launching from there and paddling was amazing on horse creek providing solitude and peace. They worked with us on a complicated checkout with some staying on while others left. I would recommend this place to anyone looking for a country experience.

River Cabin Million Dollar View! New Management!
If you're looking for a quiet place to unwind by a beautiful river, this is your spot. Perfect place to getaway for a few days of meditation and getting the mind right. Judy was so helpful and accommodating! 10/10 I will definitely be back!

Riverfront Cabin W/ Kayaks
Glamping at its best ! Was here for the rodeo with friends and family . We had the boathouse Cabin. Very pristine and clean with a super comfortable mattress. I loved waking up to the sunrise overlooking the river with my morning coffee. Hope to return here again,
Quick stats about vacation rentals with a kayak in Sarasota
Total rentals
40 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
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