Vacation rentals with a kayak in Siesta Key

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Popular amenities for Siesta Key kayak rentals

House rentals with a kayak

Guest favorite
Home in Port Charlotte
4.89 out of 5 average rating, 45 reviews

Dogs welcome, Pool, Canal, Kayaks, Fishing! Yard!

BrianRating, 5 stars1 month ago
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.
Guest favorite
Home in Port Charlotte
5 out of 5 average rating, 7 reviews

The Leaning Palm

TammieRating, 5 stars1 month ago
Joe made us feel welcome right away and they responded to everyone of our needs in a timely manner. We’ve 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!
Top guest favorite
Home in Bradenton
4.98 out of 5 average rating, 45 reviews

15 Min to Beach Entire Home! Gracies Cottage

LizaRating, 5 stars2 weeks ago
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.
Guest favorite
Home in Apollo Beach
4.92 out of 5 average rating, 12 reviews

The white lagoon Relaxing waterfront home w/ pool

Lewis GRating, 5 stars5 days ago
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.
Top guest favorite
Home in Coquina Key
4.96 out of 5 average rating, 28 reviews

Casa Coquina: waterfront, pool, hot tub, boat lift

LisaRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Siesta Key
5 out of 5 average rating, 15 reviews

Vintage Coastal

JenniferRating, 5 stars3 weeks ago
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.
Top guest favorite
Home in Sarasota
5 out of 5 average rating, 19 reviews

Modern 3 Bed 2 Bath House Backyard + Pet Friendly

MaximilianRating, 5 stars3 weeks ago
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!
Superhost
Home in St. Petersburg
4.8 out of 5 average rating, 250 reviews

Bungalow near the sea

JuliaRating, 5 stars5 days ago
Perfect for our needs. Close to parks. Clean kitchen, bath, and linens. Easy check in.

Cottage rentals with a kayak

Superhost
Cottage in Pass-a-Grille Beach
4.81 out of 5 average rating, 272 reviews

Sunny PaG Island rental w/bikes-just steps2beach

ThereseRating, 5 stars3 weeks ago
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!
Guest favorite
Cottage in Holmes Beach
5 out of 5 average rating, 6 reviews

Anna Maria Cottage w/Golf Cart

AmandaRating, 5 stars5 days ago
Our stay was great. Having the Golf Cart was so handy we didn’t have to rent one. The house is nice and clean the bedding towels. Everything was nice and clean. We would definitely stay again.
Guest favorite
Cottage in Pass-a-Grille Beach
4.87 out of 5 average rating, 166 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

CindyRating, 5 stars4 months ago
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.
Top guest favorite
Cottage in Bradenton
5 out of 5 average rating, 28 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

RenaeRating, 5 stars3 weeks ago
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!
Top guest favorite
Cottage in Englewood
5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

AnetaRating, 5 stars9 months ago
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 – 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!
Cottage in Holmes Beach
5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

KrystalRating, 5 stars20 months ago
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.
Guest favorite
Cottage in Sarasota
4.96 out of 5 average rating, 76 reviews

Cottage by the Bay - free charging, Level 2 EV

CathyRating, 5 stars5 months ago
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, 💯!
Top guest favorite
Cottage in Nokomis
4.99 out of 5 average rating, 79 reviews

New Pool Tropical Waterfront Dock & Optional Boat

BrianRating, 5 stars2 weeks ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key
  6. Rentals with a kayak