
Holiday rentals with a kayak in Sarasota Beach
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Top-rated rentals with kayak in Sarasota Beach
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House rentals with a kayak

The Shore House Private Dock Hot Tub
Great house and wonderful location. Decorated in perfect style for Siesta Key. The bikes at the property were helpful in getting around. Close to the beach, shopping, restaurants, but very chill and quiet when home. Highly recommend this house, Jenni as the host and their caretaker, Ritchie. What a fantastic vacation destination!

The Pink Riverhouse- No damage from Hurricanes
Our stay at Katie's was a wonderful experience. So much to do within the house as well as the backyard. Katie & Terry were both prompt when needed throughout the trip and made us feel at home. Katie also have great recommendations for grocery shopping which made me fall in love with the Amisb Supermarket. Also, great proximty to many attractions. We will most definitely find more time to stay here again!

Waterfront Oasis
This home is well- maintained and has lovely outdoor spaces. The artwork in the home was unique and fun, not cookie-cutter or generic. I loved that. The amenities were just what was needed to prepare meals or enjoy ourselves. The neighborhood is quiet and walkable, with friendly neighbors. Overall, this is a great location and property.

Waterfront Escape with Pool, Hot Tub & Treehouse!
We had a family of 9. The home had more than enough beds for us to feel that we had enough to host for each person plus ample room for more. The entire home was carefully supplied with plenty of kitchen cooking supplies, high quality linens, and beach and bath towels. We used every part of the house to entertain ourselves and it was hard to say goodbye after a week stay. The AMI beaches are about a 20-30 min drive, but completely worth it to have this waterfront property that has all the amenities that condos fall short on. Jason was just a text away for any of our requests. This place is a gem and we would rent again without looking elsewhere.

Sweet Siesta Cottage
Billie was an amazing host! She was extremely flexible with check-in and the cottage was great. We come to Siesta Key yearly and try to stay in walking distance to everything and this was block away from the beach and 10-15 minute walk to downtown. We didn't have car but there's parking available if needed. Will be our go-to spot going forward!

Perfect Family Getaway+ping pong, mini golf, bikes
We loved Lotte’s place:) we came down from Tampa for a quick getaway and it was incredibly comfortable and very well equipped with everything we needed. Lotte was very kind to let us bring our dog too. The home is located really close to all the fun things to do in Sarasota (smugglers mini golf, whimsy art galleries, lido beach, mote aquarium were our choices!) We were unfamiliar with the neighborhood but were blown away by how charming and lovely the immediate area is- stunning homes along the bay front- we had a really fun time strolling around with our dog- everyone was really friendly and the atmosphere was really relaxed and the foliage and gardens were beautiful. We even got to see a couple of neighborhood owls in the evening.

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks
If you’re looking for the perfect Airbnb for fishermen and vacationers are alike, this is it. This Home is elegant and extremely clean. The host are responsive and so sweet and kind. It has everything you can need , and it’s in the perfect location. We loved relaxing and watching the rain in the Florida room. We really enjoyed all the nature outside and fishing from the dock so many memories were made with our family here.

Private Home on Canal / Cal King-Heated Pool/Spa
We’ve been to Siesta Key multiple times and this is the best property we have stayed in by far. All of the interior amenities are as advertised; comfortable beds, beautiful kitchen, and a very comfortable living area. Outside, the pool and hot tub operated well and were perfect for winding down. The garage was fully stocked with bicycles, chairs, boogie boards; everything you needed for a short walk or bike ride to the beach. And finally, the location; everything is within a 10 minute walk. We didn’t need a golf cart or Uber with the exception of taking the Trolley to get fishing bait. This is an incredible location on Siesta Key, so convenient and easy to get around. If you have a small family or two couples looking to enjoy Siesta Key this is the place for you, thanks to the owners for great communication throughout! We will absolutely be back!
Cottage rentals with a kayak

Anna Maria Cottage w/Golf Cart
My son and I had a wonderful stay at this cute little cottage. Everything was clean and well-decorated, and we had everything we needed in the kitchen. We loved having the golf cart to run around in! The host also provided beach chairs and a kayak to use, which was very handy. The area is pleasant, situated in a quiet neighborhood with public tennis and basketball courts across the street. Anna Maria is a happy little island, with a lot of good food and entertainment, and a number of beach areas to choose from. Lynda was very responsive to any questions we had, and provided a lot of easy -to-follow instructions for the house, as well as lots of helpful tips about the area. We will definitely be back!

"New"Country Cottage / Lake Manatee Lakewood Ranch
I had the most beautiful time❤️The accommodations were perfect and Kristen is a very gracious host. The settings ideal with a resident horse and cow . There is a grill and a pool and a washer/dryer. The setting is very private and the space is well appointed. Kristen goes out of her way to ensure that a fun, relaxing and memorable time is had. I truly appreciated how pet friendly the property was also. It was beyond perfect😊🌸💕🐴

Oystercatcher 3min walk to sunset, bikes, kayaks
This was such a pleasant surprise! The property was brand new and offered every amenity we could want. ( loved the USB outlets strategically placed, well done and often not seen) The neighborhood was quiet and it really was a short walk to the beach, made easy with the available beach cart. This may be my first ever review after all my stays at airbnb's as it certainly deserves it. Jenn & Eddie were easy to communicate with and the vibe all around was fantastic. Thank you & we will be back!

2/2 Charming Riverfront Cottage w Deck & Kayaks
We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️

West Coast Island Retreat, Simply Adrift Cottage
By far the most relaxing vacation our family has taken. The home is even more beautiful in person than the pictures show. The host's style and decor are just perfect for a cool beachy vibe which adds to the whole experience of being on LGI. Hosts were extremely accommodating during our stay. We cannot wait to return! ☀️

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.

Good after Milton - Waterfall Pool! Beach! om
This is the second time we have stayed at a place Amy is the host for. She is wonderful to work with and her cleaning staff is amazing and always offers their assistance if they see you during your stay. I highly recommend booking with her. This has been our favorite location yet and we have stayed at several between Englewood and Fort Myers over the years. Very kid friendly too!

Cottage by the Bay - free charging, Level 2 EV
John did all he could to make our stay wonderful in his absence. He has a great caretaker who hosted us since John was on vacation, was willing to help us with kayak rentals since he wasn’t there for us to use his, had the nice bicycles ready to ride. Sorry we didn’t get to meet him and Carmen in person; they seem as wonderful as their caretaker! Had pastries and delicious bottle of wine for myself and a treat for my husband, who is not a wine drinker. Caretaker met us and gave us an orientation as soon as we arrived. Was available for anything we needed throughout our visit and had lots of connections and ideas for outings. Grateful for laundry, beach chairs, cooler, comfy bed, recliners, lanai, and all the help and generosity offered during our weeklong stay!
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
Great stay! Very spacious. Fresh eggs were a nice touch.

River Cabin Million Dollar View!
Very nice and peaceful place.. Will definitely be back again.Awesome view!!! Cozy and clean.

Riverfront Cabin W/ Kayaks
Marc and Meagan were great hosts and very friendly! We loved our studio and the surrounding property was beautiful. I would definately stay here again
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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
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park