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
A modern kitchen showcases sleek countertops and a spacious island with seating. Stainless steel appliances are complemented by a vibrant color scheme, while natural light filters through windows, highlighting the dining area visible in the background.
Home in Nokomis
4.9 out of 5 average rating, 21 reviews

Vacation ,sunny house 2 Mil beach .Pets welcome

JenRating, 5 stars4 days ago
We had a great stay. The home was spotless, quiet and well stocked. We didn't spend a lot of time at the house but was nice to come home to a quiet place after full days of fun. It was a perfect location for where we wanted to explore. The nearby beaches had lots of shells if you like shell seeking and a popular place for finding shark teeth.
Guest favorite
A grassy yard features two kayaks stored near a wooden dock, with lush greenery surrounding the area. A shade structure is visible in the background, alongside a residential home. The sky is clear, displaying a few clouds.
Home in Bradenton
5 out of 5 average rating, 69 reviews

Waterfront Home w/ Private Dock, Kayaks, and Yard!

MichelleRating, 5 stars1 week ago
Lauren and the property were both wonderful! We would definitely stay again!
Guest favorite
Two kayaks are securely positioned against a white wooden fence. Both kayaks are blue, with one resting on top of the other. Life jackets are neatly placed atop the kayaks, highlighting the opportunity for outdoor adventures in the surrounding nature.
Home in Venice
4.87 out of 5 average rating, 93 reviews

Lovely 3-bdrm waterfront home with heated pool

MichaelRating, 5 stars6 months ago
Milaā€™s place was outstanding! Spacious, well-stocked kitchen with high-end appliances, enclosed sparkling clean pool with outdoor barbecue, lounge chairs, and outdoor shower, two spacious bathrooms both with double sinks and rainfall showers, Samsung washer and dryer, three large bedrooms complete with smart TVs, and modern living and dining areas. Air conditioning was superb and the temperature could be customized in each area of the house, which was a must in the Florida summer heat. The house was comfortable, luxurious, spotless, and felt just like home. The kitchen area is a huge plus - I did a lot of cooking during my stay, so having so much counter space & all the necessary utensils and cooking equipment was lovely. The pool is HUGE and very cleanā€¦ I really enjoyed taking dips in the pool during the day & in the evening, too! Although we encountered a few small issues during our stay, Mila was incredibly responsive & friendly, and rectified each issue in a timely manner.
Guest favorite
Home in Holmes Beach
4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

DanaRating, 5 stars5 months ago
Loved this place! Looks exactly like pics. Few things I always look for- cold A/C, comfortable beds, strong water pressure and hot water when I shower. This place had all!! Place was clean and organized. Washer/dryer in garage. Pool was small but perfect after a hot day at the beach. Location was close to everything and convenient. Kit was great at communicating and very responsive. I would stay here again if I get back to the island!!!
Guest favorite
Home in Palmetto
5 out of 5 average rating, 21 reviews

The Ocean Pearl

MitchRating, 5 stars5 months ago
Awesome place to stay! They went over everything made the process very simple so my family could just relax and enjoy our vacation. Recommend 10/10
Guest favorite
A bright blue kayak is placed against a white lattice gate adorned with a colorful 'WELCOME' sign. Lush greenery and palm trees surround the entrance, creating a tropical ambiance.
Home in Sarasota
5 out of 5 average rating, 15 reviews

Your Personal Resort-7BR, Pool, Boating & More!

TinaRating, 5 stars1 month ago
Weā€™ve stayed with a large group in the Sarasota area at several different rentals, and this one is by far our favorite! Joel was incredibly welcoming, taking the time to personally meet the first guest at the house. He gave them a full tour, showing them the dock, the beach, and all the unique features of the property. The house itself is spacious, easily accommodating 12 guests with plenty of room to spread out. We made the most of the amazing amenities, including the pool, hot tub, fire pit, bocce court, and ping pong table ā€” and thatā€™s just the beginning! The house also comes equipped with brand-new bikes, beach chairs, and a convenient cart to transport them to the shore. This house really has it all and comes very well equipped with (quality) toilet paper, paper towels, tissues, soaps, shampoos etc- it really makes a difference not to be going back and forth to the store when you are on vacation!!! The kitchen is well stocked too. 5 stars all around! Thank you Joel!!!
Guest favorite
Home in Sarasota
5 out of 5 average rating, 16 reviews

Modern 3 Bed 2 Bath House Backyard + Pet Friendly

JesusRating, 5 stars1 month ago
Great house in a convenient locationā€”lots nearby, including supermarket and restaurants. The house had plenty of room Joseph was very responsive and a great host. Will definitely recommend and book again.
Superhost
A lush green lawn is framed by tall trees, leading to a calm waterway. A kayak rests near the water's edge, surrounded by dense foliage. A picnic table is positioned nearby, offering a serene outdoor space for relaxation and enjoyment.
Home in Nokomis
4.78 out of 5 average rating, 9 reviews

Crystal Cottage, a beachy cottage

SandraRating, 5 stars3 weeks ago
Thank you to Diana we really enjoyed our stay. She communicated very quickly when there was an issue and was resolved with in the day. Will be checking our calendar for another stay next winter thank you again for making our stay so pleasurable. The cottage is cosy and comfortable in a great quiet location.

Cottage rentals with a kayak

Guest favorite
Cottage in Holmes Beach
5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

RebeccaRating, 5 stars5 months ago
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.
A wooden bench is positioned on sandy ground near a serene beach. The clear blue sky is visible above, complimented by scattered clouds. The gentle waves of the ocean reflect shades of turquoise, creating a calming coastal view.
Cottage in Holmes Beach
5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

KrystalRating, 5 stars18 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
A brightly colored kayak is seen floating on calm waters, equipped with a yellow sail and a comfortable seating area. Lush greenery lines the distant shoreline, providing a natural backdrop for a relaxing water sport experience.
Cottage in Sarasota
4.96 out of 5 average rating, 76 reviews

Cottage by the Bay - free Level 2 EV charging

CathyRating, 5 stars2 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, šŸ’Æ!
Guest favorite
Cottage in Bradenton
5 out of 5 average rating, 21 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

JuliaRating, 5 stars1 week ago
Really beautiful spot. We loved sitting on the patio and bird watching with the binoculars and bird ID book that was there. My dog loved it too, lots of different spots for her to hang out. This is definitely a great spot to enjoy the outdoors and take a break from a busy life.
Guest favorite
A wooden deck extends over a serene canal, featuring a bright yellow kayak resting beside lounge chairs. Lush greenery surrounds the scene, offering a sense of privacy and tranquility. Morning light casts gentle reflections on the water's surface, enhancing the peaceful atmosphere.
Cottage in Anna Maria
4.89 out of 5 average rating, 35 reviews

Snail's Pace: On Canal, Kayaks & Dog Friendly

HalieRating, 5 stars5 months ago
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.
Guest favorite
Cottage in Nokomis
4.99 out of 5 average rating, 76 reviews

New Pool Tropical Waterfront Dock & Optional Boat

RayRating, 5 stars4 days ago
We could not have picked a better place for our stay. House was well kept with quire and peaceful surrounds and very relaxing heated pool. We will definitely come back.

Quick stats about vacation rentals with a kayak in Siesta Key

  • Total rentals

    40 properties

  • Nightly prices starting at

    $140 before taxes and fees

  • Total number of reviews

    1.8K 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