
Vacation rentals with a 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.

The Bays Edge Retreat Waterfront (Sleeps 13)
The house is located in a beautiful neighborhood. It is so beautiful and beyond. It has the best view and a lot of areas to enjoy the sunset. I loved the games that Robert has, it allows you to have a family time. In overall I spend a wonderful weekend and I was able to celebrate my wedding and baby shower over there with the family and close friends.

15 Min to Beach Entire Home! Gracies Cottage
Nicoleâs 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.

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
Great house in a convenient locationâlots 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.

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 Home w/ guest house!
Spacious with lots of fun things to do. Brock was a great host and when we realized my son lost something at the house, they searched for it and mailed it to us- amazing! Really great place with good people taking care of it. Definitely would stay again!

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks
The house/location/amenities were all as advertisedâvery clean and included everything you could need. We loved the fenced in yard, canal water access, and available kayaks. We will recommend to family and friends.
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 isnât 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 wouldnât 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 Lisaâs great responsiveness.

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 â 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, đŻ!

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 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
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
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- Lido Key Beach
- Bean Point Beach
- Amalie Arena
- North Beach
- Raymond James Stadium
- Vinoy Park
- Coquina Beach
- Curtis Hixon Waterfront Park
- Tampa Theatre
- Fort De Soto Park
- Tropicana Field
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- Splash Harbour Water Park
- River Strand Golf and Country Club
- Lakewood National Golf Club
- Englewood Beach
- Alafia River State Park
- Sunken Gardens
- Tara Golf & Country Club
- Courtney Campbell Causeway Beach
- North Beach At Fort DeSoto Park
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