Vacation rentals with a kayak in Anna Maria Island

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Anna Maria Island

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Superhost

A serene saltwater pool reflects the surrounding palm trees and evening sky. Lounge chairs are positioned along the deck, offering comfort beside the tranquil water. The dock is visible in the background, enhancing the waterfront ambiance.

Home in Longboat Key

4.88 out of 5 average rating, 120 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Top guest favorite

Three kayaks are positioned on the sandy shore, ready for use. A bright yellow kayak stands next to two blue kayaks, creating a vibrant contrast against the natural surroundings. In the background, palm trees and a dock are visible, indicating access to the water.

Home in Apollo Beach

4.93 out of 5 average rating, 104 reviews

Apollo Beach Waterfront Amazing Pool Oasis

Forget your worries in this spacious and serene space. You are invited to our private oasis waterfront home in Apollo Beach. Enjoy our backyard, from the outdoor living space, dining area, sun loungers, games, and the amazing pool overlooking the canal; Watch dolphins & manatees as you relax in the pool. Home equipped with a large kitchen, dining room, 2 bathrooms, 2 bedrooms and an additional living room with a closet and sleeping sofa that can be used as a private 3rd bedroom. LIC#DWE3913431

Superhost

Home in Tampa

4.78 out of 5 average rating, 113 reviews

Waterfront Oasis! Kayaks,Hot Tub

This one of a kind waterfront home is the perfect oasis while still being close to everything Tampa Bay has to offer. 10 minutes from TPA, downtown Tampa, Bush Gardens, Raymond stadium and 30 min to St Pete/ Clearwater Beach/ Dunedin. The natural canals right behind the house are some of the most memorizing natural areas you’ll find in all of Florida! We have 2 tandem kayaks for some epic exploring, a private dock w/ lounger & fire pit, and a screened lanai with hot tub over looking the water!

Superhost

A wooden dock extends over calm water, providing clear views of the natural surroundings. Lush greenery borders the shoreline, while bright blue skies above enhance the serene atmosphere. The dock features a wide pathway, inviting exploration along the tranquil lake.

Guesthouse in St. Petersburg

4.83 out of 5 average rating, 125 reviews

Guest House by the Lake

Large guest suite less than 10 minutes to both downtown St Pete and St Pete Beach. Walk out the back and you'll find yourself only a minute away from a large lake and a beautiful park. There is a golf range and practice green area located in the same park. The space is large and completely private. You will find everything you need - full bathroom, large closet, full table/desk, kitchenette, wifi/Netflix, yard/grill, etc. Also available to use: kayak, golf clubs, beach towels, fishing poles

Superhost

Two kayaks are positioned on a grassy area near the water's edge. One kayak is blue and the other yellow, with paddles resting inside. Lush green trees frame the scene, and a dock is visible in the background, leading to calm waters.

Island in Gibsonton

4.8 out of 5 average rating, 5 reviews

Island Retreat Florida

Please read before booking! Ever wonder what it would be like to stay on a deserted island? This is truly an adventure you will never forget. Once you land in paradise you will wander thru the looping trail system to find your campsite. There are (4) campsites with elevated tent platforms tucked in the trees. Settle in and gather wood to build a fire in one of the (2) 8 foot concrete fire pits. There is an outhouse on the property for a more enjoyable stay. We are also working on a shower.

Superhost

A shaded seating area is positioned on lush green grass next to calm waters, with a large tree providing cover. A small boat can be seen in the distance on the water, surrounded by greenery along the shore.

Condo in Ruskin

4.74 out of 5 average rating, 155 reviews

Little Harbor Resort #109 Tampa Bay FL Beach, Pool

Little Harbor Resort is a paradise packed with amenities. Enjoy 2 pools, Jacuzzi, Beach on Tampa Bay (not Gulf), 2 restaurants, Tiki Bar, tennis, pickleball, basketball, playground, fishing charters, sightseeing cruises, and Freedom Boat Club. The Inn at Little Harbor River Delight Studio is a ground-floor, non-smoking studio which features a kitchenette, fridge, microwave, sink, in counter hotplate, dishwasher, coffee maker with two luxurious queen beds, and captivating island decor.

Guest favorite

A private balcony offers serene river views, framed by lush foliage and a palm tree. Two cushioned chairs sit beside a small glass table, providing a cozy space for relaxation while enjoying the surroundings under a partly cloudy sky.

Cabin in Ruskin

4.91 out of 5 average rating, 11 reviews

River Cabin Million Dollar View! New Management!

Enjoy our unique, peaceful and modern on the river cabin! Wake up to a mesmerizing river view from your private balcony or our dock! This is all you can ask for to relax, fish or just enjoy the day while watching dolphins, manatees and more at this unique and tranquil getaway. Bring your boat and dock at our private dock or enjoy fishing or sun bathing with your favorite refreshment. Grill or just enjoy the beautiful river from our gazebo! Close to many beaches and restaurants!

Superhost

A private heated pool is surrounded by a spacious deck featuring lounge chairs and a dining area. Palm trees provide shade while boats are visible at the dock. String lights overhead create a relaxed ambiance, and the tranquil water reflects the blue sky.

Home in Indian Rocks Beach

4.97 out of 5 average rating, 115 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

Superhost

A well-lit living area features large windows allowing natural light to fill the space. A small dining table accompanies four chairs, while a comfortable seating arrangement includes a blue sofa and an accent chair. Artwork adorns the walls, enhancing the inviting atmosphere.

Condo in Clearwater

4.83 out of 5 average rating, 118 reviews

Direct Waterfront "The Lily Pad" Walk to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

Superhost

Two kayaks, one orange and one beige, are stored beneath a wooden staircase. A rack holds multiple bicycles, hinting at recreational options nearby. The scene is framed by wooden fencing and soft gravel underfoot, creating a relaxed outdoor environment.

Apartment in St. Petersburg

4.81 out of 5 average rating, 135 reviews

Sunshine St. Pete | 400ft² | bikes | kayak|netflix

♡ 400ft² private craftsman studio apartment on shared property ♡ ☞ Walk Score 82 (walk to cafes, dining, shopping..) ☞ Bike Score 75 (2 bikes provided) ☞ Memory foam mattress + sofa couch ☞ Fully equipped + stocked kitchen ☞ Free kayaks + beach gear ☞ Beach gear provided ☞ Onsite parking ☞ Swivel Smart TV w/ Netflix ☞ 214Mbps Wi-Fi ☞ AC & Heat 5 min → Salvador Dall Museum, Vinoy Park, St. Pete Pier 15 min → Airport & St Pete Beach

Guest favorite

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

4.91 out of 5 average rating, 113 reviews

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.

Superhost

Two charming structures are situated by the water's edge, surrounded by lush greenery. A patio with red chairs invites relaxation, while the reflection in the calm water enhances the serene surroundings. The area is ideal for outdoor enjoyment and exploration.

Apartment in Tampa

4.77 out of 5 average rating, 101 reviews

Kayaks & Firepit Mins to Dwntwn!

River Front One Bedroom Apartment in Trendy Seminole Heights, the best Restaurant District In Tampa -Fast Wifi and Smart TV -Includes Use of Kayaks and Canoes -Wood Burning Fire Pit -15 Minutes from Cypress Point Park Beach and the Airport and YBOR City, the Mid Florida Ampitheatre, and the Seminole Casino -10 Minutes from Downtown, the Convention Center, RiverWalk and Armature Works, and Julian Lane Park

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What guests are saying

NEW! The Seaside Retreat (FREE heated pool)

4.99 out of 5 average rating, 85 reviews1 month ago

This home was as clean, if not more, than some of the nicest places, even hotels, that we have stayed at. Updated beautifully, you couldn't convince me that some of the work wasn't completed yesterday, it was immaculate. We traveled with our toddler, and Nancy already had a pack and play, highchair, appropriate sized life vests, and toys. We felt welcomed and comfortable. The pool area is gorgeous and spacious, we enjoyed the heated pool daily. Even on a chilly (66 degree) day, we still swam. A short distance to Tampa, we recommended planning to eat most meals in the Tampa area, as around Apollo Beach we were disappointed by the selection. Not the hosts fault! We would readily stay again, just would have needed to pick up more groceries to cook (publix is close!) or plan better for meals out. We enjoyed the Florida Aquarium in Tampa, the Manatee Observation in Apollo Beach, and even took a day trip to Anna Maria Island. We enjoyed our stay thoroughly and look forward to visiting again.

Home in Apollo Beach

What guests are saying

Rambling River Retreat on the Manatee River

4.93 out of 5 average rating, 81 reviews2 days ago

What a Gorgeous and unique Airbnb. I loved the history behind the house and its tie to the Nitty Gritty Dirt Band. It truly felt like a little piece of history. The view out the kitchen window alone was worth the stay. Most peaceful cup of coffee I’ve had in a long time. The beds were comfy, the decor was modern yet meaningful. We partook in the kids game selection. We truly enjoyed our stay. I look forward to our next visit. We even meet and chatted with Wylan on the day of our departure and honestly couldn’t have been a nicer more welcoming host. A big thank you again for opening your home to us!

Home in Bradenton

What guests are saying

Gulf Views! 2 BR- Quiet-Canal-Htd Pool-Kayak/SUP

4.98 out of 5 average rating, 47 reviews4 weeks ago

We visited the Siesta Key area during spring break and were so glad we chose Suzanne’s peaceful and private condo. The walk to Turtle Beach, Trolley Stop, and restaurants was easy and enjoyable. The condo is prettier than the pictures and all the many amenities make the stay special. Suzanne is a wonderful host who responds quickly to any question and anticipates your needs. Her information booklet is very organized and full of information to make the vacation stress- free. We had a wonderful dinner at Ophelia’s by the Bay (within walking distance). It is a bit pricey but located in a beautiful waterfront setting . Our meal was excellent. We also enjoyed brunch at Sun Garden Cafe and lunch at Phillippi Oyster Bar.

Condo in Sarasota

What guests are saying

Waterfront Duplex- kayaks, SUP, 3 blocks to beach

5 out of 5 average rating, 50 reviews7 months ago

Our family recently enjoyed a fantastic vacation in Indian Rocks Florida, and our stay this Airbnb exceeded all expectations. Nicole had thoughtfully provided every provision we could possibly need, making our stay feel like a home away from home. The property was impeccably clean, and the attention to detail was evident in every corner. The comfort of the accommodations truly enhanced our overall enjoyment of the trip. One of the highlights of our stay was the exceptional amenities offered here. The outdoor area was quite large, offering a perfect spot for relaxation, entertaining and enjoyment. Each element contributed to the overall allure of this hidden gem in Indian Rocks, Florida. We want to extend our heartfelt thanks to the Nicole for making our stay so memorable. Their hospitality and attention to detail did not go unnoticed, and we genuinely appreciate it. Warm Regards, Tasha Mack & Family

Home in Indian Rocks Beach

What guests are saying

Beautiful MidCentury Modern Home

4.95 out of 5 average rating, 21 reviews1 month ago

Michael's home was beautiful! It was exceptionally quiet, perfect for sleeping. The kitchen is spotless, well stocked, very organized and inviting to use. My favorite space was the lanai. We enjoyed the outdoor space for coffee each morning, and a glass of wine in the evening. Neighborhood is safe, friendly, walkable, with beautiful sunsets by the water down the street. Michael was very helpful and immediately responsive when we had some travel issues due to weather.

Home in Sarasota

What guests are saying

2BR Beach Retreat - Free Stays for Furry Friends!

5 out of 5 average rating, 10 reviews1 week ago

We had a great stay! First and foremost, the home was extremely clean and in great condition, as well as beds super comfortable. I also loved that a lot of the products used in the house were clean/organic products. Hosts are super helpful and responsive! Answered any questions we had right away. We had our two toddlers (two and four) and the walk to the beach was a breeze! About a 5 min walk and great, very safe area with not much traffic being the house is on a dead end. So glad we found this place and would definitely return!

Townhouse in Indian Rocks Beach

What guests are saying

Waterfront Private Dock 4BR/2 Bath kayaks/Hot Tub!

4.97 out of 5 average rating, 34 reviews2 weeks ago

We had a wonderful time! The house and all accommodations were amazing. Awesome quiet location with everything that we needed, safe neighborhood. We were able to sit in the backyard and watch the manatees and able to relax and unwind in the hot tub. Host went above and beyond to make sure we had what we needed, was quick to respond to questions and reached out to us to see if we had questions and offer suggestions. Highly recommend, would definitely stay again!

Home in Clearwater

What guests are saying

Lagoon, pool, the Catamaran at Siesta Key Bungalow

4.89 out of 5 average rating, 9 reviews8 months ago

My family absolutely loved Kyle’s Airbnb! It was the perfect place for our family vacation with a 6 year old and 9 month old. He had so many extra child/ baby necessities that made our family trip run smoothly. The playpen, baby and kid toys, plus the baby video monitor helped immensely and allowed mom and dad to relax and enjoy, knowing our baby was safe. The beach load out wagon was the cherry on top! Made our beach days with the kids headache free. Kid beach toys, umbrellas, chairs and a wagon! Plus beach towels. The laundry onsite was an extra touch as we could always have clean clothes or towels in hand. The whole grounds is stunning as well as the pool and dock! The beds were so comfy and the place was clean and clutter free. What a joy it was to stay for the week. Kyle, was an amazing host with clear and fast communication. He went above and beyond to make sure our stay was perfect. I could go on and on! Thank you so much. We will definitely be back!

Bungalow in Siesta Key

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