Holiday rentals with a kayak in Anna Maria

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Top-rated rentals with kayak in Anna Maria

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

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Top guest favourite

Home in Apollo Beach

4.93 out of 5 average rating, 105 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

Top guest favourite

Apartment in Nokomis

5 out of 5 average rating, 49 reviews

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

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!

Top guest favourite

Bungalow in Oldsmar

4.98 out of 5 average rating, 102 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Superhost

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.

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Apartment 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 favourite

Cabin in Ruskin

4.92 out of 5 average rating, 12 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

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.

Guest favourite

Home in Tarpon Springs

4.95 out of 5 average rating, 221 reviews

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

Superhost

Townhouse in Ruskin

4.94 out of 5 average rating, 226 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

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Apartment in Clearwater Beach

4.83 out of 5 average rating, 119 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! 🌅🏝️🚤

Guest favourite

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.