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

Tranquility Bay
We had an amazing time!! It was even better than the pictures if that’s possible. Beautiful views, amazing outdoor space, tons of comfortable places for people to sleep. We had a big group and everyone was comfortable and loved it. The kayaks and paddle boards were a nice bonus too, and we loved walking to Englewood beach! Host was very responsive and helpful if we ever needed her. We would love to come back here.

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
Nicole’s home was very comfortable. It was well stocked with everything u could need. The bed was incredibly comfortable! The house was spotless. Nicole was an excellent communicator & took the time to check in on me. Having to enter & park in the back off the alley was not idea but it worked. The game room was really cute & a fun place to play. I highly recommend this property & host.

Summer House longboat key
My family and I would like to thank Chris for allowing us to stay at his beautiful beach house that was full of all the things we needed to feel at home. Chris responded to our messages very promptly and he even checked in on us to make sure we were doing well. Thank you Chris for a great experience on Long Boat Key; my family and I are very grateful 😁

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.

5 Bed/4 Bath Waterfront "Lay Low" in Apollo Beach
We just got back from a week at Mary's wonderful home. There were 9 of us and there was plenty of room for all. EVERYONE loved the house. 3 stories AND it has an elevator! Great for transporting luggage It is decorated so beautiful with comfortable furnishings. Mary is a wonderful host, easy to work with, informative and swift to answer any questions. This is the perfect spot for a large family or group of friends. The kitchen has everything you need. The game room was so much fun. We spent a lot of time in the hot tub and pool. You can fish off their dock and kayaks are provided! There are 3 great restaurants within walking distance. A short drive or walk around the corner brings you to a nice park to watch the sunset on Tampa Bay. We enjoyed watching 2 dolphins daily on the canal from the spacious balconies. Sunrise, sunsets, a full moon, and 2 space shuttle lift offs. Absolutely perfect!

Waterfront Key West Style Home
Loved this place!! Short distance to many places! The house was better than pictures! Loved the porch! Would definitely stay here again!

Sea Turtle Cottage
This place was amazing! We had a very short stay but after visiting we would come back in a heartbeat! The backyard patio was awesome, the house is equipped with everything you need, very clean, and perfect if traveling with kids! Our hosts were very communicative and all around our experience and stay was perfect!
Cottages with a kayak

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.

Free kayak/bikes/walk to beach/full cottage #1
I had the best time there is was so peaceful and beautiful they had amazing restaurants and a beautiful beach, me and my mom stayed there for my 16th birthday and it was amazing I would totally recommend staying there we are definitely going to be coming back here soon!

2/2 Charming Riverfront Cottage w Deck & Kayaks
A charming place on the Braden River. We loved having the option to kayak on the river or drive to the beach each day. We switched off to keep things interesting. The cookout facilities were fantastic. We never used the charcoal grill but we might have! The turtles, gators and birds on the river were endlessly fascinating.

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
40 properties
Nightly prices starting at
$223 AUD 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
- North Beach
- Raymond James Stadium
- Vinoy Park
- Coquina Beach
- Curtis Hixon Waterfront Park
- Tampa Theatre
- Fort De Soto Park
- Tropicana Field
- Manasota Key Beach
- Splash Harbour Water Park
- Lakewood National Golf Club
- Streamsong Resort
- River Strand Golf and Country Club
- Englewood Beach
- Alafia River State Park
- Marie Selby Botanical Gardens
- Florida Botanical Gardens
- Bayou Club