
Vacation rentals with a kayak in Siesta Key
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Top-rated kayak rentals in Siesta Key
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House rentals with a kayak

Dogs welcome, Pool, Canal, Kayaks, Fishing! Yard!
My family and I had a great stay, everything was exactly what we expected based on the listing. The house was perfect, clean, and comfortable, the neighborhood was nice and quiet, and we loved the canal. The house had everything we could ever need for our visit and that was great too. We have zero complaints and would definately stay again.

The Leaning Palm
Joe made us feel welcome right away and they responded to everyone of our needs in a timely manner. Weâve never been there before and they helped us navigate our way to the destinations. Great for a large family with a very well equipped kitchen. There were nice sized TVs for rainy daysand quick access to all the stores we need to get to. We loved every minute and appreciated our Host being so friendly. Great for a long stay!

15 Min to Beach Entire Home! Gracies Cottage
The house was gorgeous! Also, Nicole was an amazing host. She made sure to make us feel at home and was very responsive to all of the questions that we have.

The white lagoon Relaxing waterfront home w/ pool
The pictures did not do this house justice. It is absolutely beautiful. Clean. Felt like home to my family. Eva was very responsive and easy to work with. We enjoyed our stay very much and enjoyed exploring the area by boat and by car. Love the pool and boat dock.

Casa Coquina: waterfront, pool, hot tub, boat lift
This home is amazing. It is very comfortable and peaceful. The water view and ability to walk down and sit on the dock over the water is incredible. The lush landscaping is so pretty. The pool and hot tub are so relaxing! There are plenty of items to help with cooking in the lovely kitchen. The artwork and decorations are very interesting. The hosts are extremely responsive to anything you may need. We had a wonderful stay and plan to use this house again when we return. Great stay. Great home. Great host.

Vintage Coastal
This place was absolutely gorgeous. Knowing that we were the first people to stay here after the hurricane damage made us a bit nervous. The property was completely fixed up and everything was perfect. The communication before our arrival was superb.

Modern 3 Bed 2 Bath House Backyard + Pet Friendly
Joe's place feels like a real home - many AirBnBs can feel like a hotel with a little more space - Joe's house was not that! Complete with a ton of my personal favorite books, tons of kitchen utensils/supplies, a desk, and more. The huge fenced in backyard was perfect for grilling and our dogs. The location is right off of a main road that takes you to shopping/amenities within minutes. If you're looking for a great place to feel comfortable while visiting Sarasota, we'd recommend Joe's property to anyone!

Bungalow near the sea
Perfect for our needs. Close to parks. Clean kitchen, bath, and linens. Easy check in.
Cottage rentals with a kayak

Sunny PaG Island rental w/bikes-just steps2beach
Perfect Coastal Getaway My sister and I were looking for a relaxing beach retreat, and this place exceeded our expectations. From the moment we arrived, we were impressed by the charming and cozy atmosphere. The decor perfectly encapsulated the beachy vibe, making us feel right at home. The accommodation was clean, well-maintained, and equipped with everything we needed for a comfortable stay. One of the highlights of our visit was the proximity to the beach. Just a short walk away, we enjoyed sun-filled days lounging on the soft sand and taking refreshing dips in the ocean. It was so convenient to have the beach just minutes from our doorstep, allowing us to soak up the sun whenever we pleased. The neighborhood is lovely, with plenty of quaint shops and delicious dining options nearby. We loved exploring the area and trying out local restaurants. Overall, our stay here was an unforgettable experience. We highly recommend this spot to anyone looking for a charming beach escape!

Anna Maria Cottage w/Golf Cart
Our stay was great. Having the Golf Cart was so handy we didnât have to rent one. The house is nice and clean the bedding towels. Everything was nice and clean. We would definitely stay again.

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 isnât 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 wouldnât 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 Lisaâs great responsiveness.

2/2 Charming Riverfront Cottage w Deck & Kayaks
We love this little cottage! The view from the back is phenomenal - we even saw a couple gators. The set up is so good for pets. The cottage has everything you need and the primary bed is more comfortable than a hotel bed. 10/10 and would def stay here again!

The Coastal Oasis. Only 8 minutes from the Beach!
Absolutely fantastic stay! This Airbnb is a gem, located just 8 minutes away from the beach, making it incredibly convenient for beach lovers. The cleanliness of the place is impeccable â it was super duper clean and well-maintained. The hosts have thought of everything you could possibly need during your stay. From a fully stocked kitchen to cozy linens and even beach gear, they've got it all covered. The attention to detail and thoughtful amenities truly made our stay comfortable and enjoyable. Highly recommend this place for anyone looking for a perfect beach getaway!

Steps To The Beach, Private & Heated Pool, Renovat
Location is great, less than 2 minute, very easy walk, to the beach. Quiet street and properties on either side were not disturbing. There is no grass, so if you bring your furbaby, there are walkable areas to let them do their business. The house itself was very clean and not cluttered. Kitchen is well stocked. There is a great washer/dryer combo. There is no screen for the pool, but a quick daily skimming was sufficient. The pool was clean....no algae. There's a beach cart, chairs, floats, beach towels, etc there, so no need to bring your own. The house is older and in the afternoons it gets very warm (78-80) despite keeping blinds closed and setting ac at 74. We were there in the middle of August and we live in the South so are used to the heat so it wasn't that big of a deal for us. There was a box fan that we used.

Cottage by the Bay - free charging, Level 2 EV
The Cottage on the Bay was exactly as described. It was very inviting, clean and comfortable. Jack and Carmen were the most hospitable hosts that you could ever meet on your journey. Their communication as hosts was excellent and prompt from the beginning and throughout my stay. They explained that a welcome gift of food and drink is provided for each guest. I explained my food allergies to them. Jack thoughtfully provided substitutions for me instead. The kitchen had a generous array of utensils, pots, pans and essentials. This was an excellent plus for me since cooking was necessary due to my allergies. I considered the location excellent because it is near the airport. This made transportation convenient anywhere from there. The views of the Sarasota Bay sunset were wonderful. I loved walking around the scenic and quiet area. I enjoyed the best vacation stay at the Cottage. Jack & Carmen's hospitality and care took this trip over the top. They are the total package, đŻ!

New Pool Tropical Waterfront Dock & Optional Boat
Great home! The pool and the canal being right out the back door, well lets just say, it made the coffee mornings so much better. We didn't get t see any manatees, but heard it was the time of year, so we plan on going back when they are "in season". Overall great home with free access to kayaks, bikes, and pool rafts.
Quick stats about vacation rentals with a kayak in Siesta Key
Total rentals
50 properties
Nightly prices starting at
$140 before taxes and fees
Total number of reviews
2K 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
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Raymond James Stadium
- Gulfport Beach Recreation Area
- North Beach
- Coquina Beach
- Vinoy Park
- Manasota Key Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Streamsong Resort
- Jannus Live
- Splash Harbour Water Park
- Myakka River State Park
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