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

Dogs welcome, Pool, Canal, Kayaks, Fishing! Yard!
We really enjoyed our stay at David's place. It was clean and comfortably furnished. The neighborhood was safe to take walks and the people are friendly. The Bluetooth stereo is really neat to use, just put XM on the phone and it linked to the stereo. The pool is not heated but we did go in and it was refreshing after golf on a warm day. The kitchen is well stocked with essentials, except for wine glasses. We've never been puzzle people but we spent hours on one of the 1,000-piece puzzles David provided. There are Kayaks, horseshoes, and cornhole games to keep you busy, but we enjoyed sitting by the pool in the afternoon the most.

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
Place was great. Eva was very responsive. Pool and backyard were great. Everything you need is within 10 minutes. A little unwelcoming in the neighborhood with all of the say no to air bnb signs around….But nothing anyone can do about that. We’d definitely go back!

Casa Coquina: waterfront, pool, hot tub, boat lift
Casa Coquina is absolutely a beatiful place t and has everything you need for your stay at the home. Chuck and Jilla are very responsive and gave great recommendations on places to go and eat while you are in St. Petersburg. Besides loving the pool and spa we used the dock for fishing and was able to see a manatee , which was my favorite part of our trip.

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!

5 Bed/4 Bath Waterfront "Lay Low" in Apollo Beach
Beautiful, well maintained and stocked property(toilet paper, trash bags etc)!! We enjoyed fishing off the dock as well as relaxing in the hot tub while the kids played in the pool! The beds were comfy home was clean and comfortable! Didn’t hear a complaint from anyone! We loved that the home was located walking distance to restaurants!

Waterfront Key West Style Home
beautiful home, pool and property

Bungalow near the sea
Great place and great location!
Cottage rentals with a kayak

Sunny PaG Island rental w/bikes-just steps2beach
Quaint place and location so perfect for beach! Will return for sure!!!

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.

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 – 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, 💯!

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.
Quick stats about holiday rentals with a kayak in Siesta Key
Total rentals
50 properties
Nightly prices starting at
£106 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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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Amalie Arena
- Raymond James Stadium
- North Beach
- Vinoy Park
- Coquina Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Myakka River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall
- Lakewood National Golf Club
- Splash Harbour Water Park
- Jannus Live
- Sunken Gardens
- Englewood Beach
- River Strand Golf and Country Club