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Vacation rentals with a kayak near Anna Maria Island

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Top-rated kayak rentals near Anna Maria Island

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A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.

Cottage in St. Pete Beach

4.8 out of 5 average rating, 289 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Welcome to your beach getaway! This cheerful, sun-soaked cottage is steps from the sand—or your next ice cream or seaside meal at a nearby restaurant. Perfect for couples or solo travelers, a comfy queen bed, a breezy living room, and a kitchen and dining area. Sip your morning drink on the upstairs porch as salty breezes drift by, or fire up the BBQ on the downstairs patio. Two bikes are yours to cruise the island like a local—Everything you need for a relaxing, joy-filled beach escape is here

Top guest favorite

A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.

Home in Terra Ceia

4.98 out of 5 average rating, 105 reviews

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

An elegant outdoor space features a heated pool surrounded by stylish stone pavers and tropical landscaping. Large covered porches provide shaded seating areas with colorful furniture, while palm trees enhance the inviting atmosphere of the home's exterior.

Home in Bradenton

4.95 out of 5 average rating, 150 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Top guest favorite

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

4.99 out of 5 average rating, 135 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

The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.

Home in Bradenton

4.79 out of 5 average rating, 350 reviews

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

Top guest favorite

Tiny home in Sarasota

4.96 out of 5 average rating, 371 reviews

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Top guest favorite

A spacious outdoor area features a serene pool, surrounded by a deck for lounging. Tall palm trees provide shade, and a dining area with ample seating overlooks the waterway. The calm surface of the water enhances the tranquil setting of this private waterfront home.

Home in Apollo Beach

4.94 out of 5 average rating, 126 reviews

Waterfront Oasis: Pool, Kayaks & Sunset views

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Large sliding glass doors open to waterfront views, revealing a sunlit space with a modern kitchenette. A small dining table with two chairs is set near the doors, and a flat-screen TV is mounted on the wall, complementing the serene aquatic surroundings.

Houseboat in Clearwater

4.85 out of 5 average rating, 108 reviews

Breathtaking Beachy Houseboat on Clearwater Island

🌊 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! 🌅🏝️🚤 NO PETS ALLOWED.

A living area features a plush blue sofa and matching lounge chair, placed on a light blue and white striped rug. Large sliding glass doors open to a balcony, allowing natural light to illuminate the space. A coffee table and a side table complete the inviting setup.

Townhouse in Ruskin

4.94 out of 5 average rating, 234 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.

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

Home in Bradenton Beach

4.96 out of 5 average rating, 109 reviews

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

Top guest favorite

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

Home in Anna Maria

4.95 out of 5 average rating, 184 reviews

Discounted September and October Stays w/Dock-Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Top guest favorite

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

5 out of 5 average rating, 145 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Popular amenities for kayak rentals near Anna Maria Island

Free parking on premises

Air conditioning

House rentals with a kayak

A screened-in patio surrounds a clear swimming pool, offering views of a serene waterfront. Comfortable lounge chairs line the poolside, complemented by palm trees in the background. The tranquil setting is enhanced by the inviting blue hues of the water.

Home in Bradenton

4.9 out of 5 average rating, 21 reviews

Oceanside 3BR with Private Pool & Boat Lift

Top guest favorite

A scenic view from a spacious balcony showcases the tranquil waters of the Manatee River. Comfortable white Adirondack chairs are positioned for relaxation, overlooking a heated pool and the glistening water, with lush greenery lining the waterfront.

Home in Ellenton

5 out of 5 average rating, 44 reviews

The Pink Riverhouse- Waterfront Paradise

An outdoor area features a heated pool surrounded by lounge chairs, a pickleball court, and a putting green, all enhanced by tropical landscaping. The interior reveals a comfortable game room with arcade games and modern amenities, providing a relaxing atmosphere for all guests.

Home in Bradenton

5 out of 5 average rating, 16 reviews

Fall Special! - Family Fun - 9 min to Beach

Home in Indian Rocks Beach

5 out of 5 average rating, 8 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat

An inviting living area features a spacious sectional sofa adorned with vibrant pillows and a cozy fireplace. Large glass doors provide natural light and views of the outdoor pool area, while a unique coffee table complements the mid-century modern design.

Home in Siesta Key

5 out of 5 average rating, 5 reviews

Mid-Century Modern, Pool, Mins to Siesta Key Beach

An aerial view captures the canalfront property, showcasing the large pool and spa surrounded by tropical landscaping. The private dock accommodates a boat, while a beach area is visible with lounge chairs and palm trees enhancing the waterfront setting.

Home in Apollo Beach

5 out of 5 average rating, 6 reviews

*New* Waterfront Retreat: Pool, Spa, Dock & Views

Top guest favorite

An inviting outdoor space showcases a heated pool surrounded by a screened-in patio. String lights gently illuminate the area, highlighting cozy seating and a dining table, while a BBQ grill is positioned conveniently for outdoor meals.

Home in Bradenton

5 out of 5 average rating, 13 reviews

Private Pool | Fire Pit | 8 miles to AMI

A screened enclosure surrounds a private swimming pool, providing a sunny outdoor space. Comfortable seating is visible alongside a dining area with a table and chairs. Lush greenery and palm trees can be seen in the background, enhancing the tropical atmosphere.

Home in Bradenton

5 out of 5 average rating, 11 reviews

“Topside” luxury home in Cortez Village

Cottage rentals with a kayak

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

Cottage in Clearwater

4.77 out of 5 average rating, 155 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

A modern kitchen features white shiplap walls and an island with a light marble countertop. Four wooden bar stools with caned backs are positioned at the island. Pendant lights with woven shades hang above, and silver appliances are visible in the background.

Cottage in Holmes Beach

4.9 out of 5 average rating, 10 reviews

Anna Maria Cottage w/Golf Cart

A wooden boardwalk leads directly to the beach, framed by sandy dunes and swaying grass. The clear blue sky meets the calm waters of the Gulf, creating an inviting scene for beachgoers. The soft beach sand stretches out, blending seamlessly into the horizon.

Cottage in St. Pete Beach

4.88 out of 5 average rating, 178 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

The cottage exterior features a light blue facade with a centered front door, flanked by two large windows. A small porch with a bench is present, along with potted plants. A single-car garage is visible, and a manicured lawn surrounds the home.

Cottage in Sarasota

5 out of 5 average rating, 6 reviews

Cottage & Tree ~ by the Sea

Cottage in Bradenton

4.95 out of 5 average rating, 43 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Top guest favorite

Cottage in Tampa

4.97 out of 5 average rating, 221 reviews

Bay Lake Cottage

Top guest favorite

A cozy living space features a dark leather couch and a decorative wooden coffee table. Natural light streams through large windows adorned with blue patterned curtains. A flat-screen TV is mounted on the wall, and a wooden cabinet displays nautical-themed decor.

Cottage in Riverview

4.93 out of 5 average rating, 87 reviews

Alafia River Cottage

A wooden bench is positioned on sandy ground near a serene beach. The clear blue sky is visible above, complimented by scattered clouds. The gentle waves of the ocean reflect shades of turquoise, creating a calming coastal view.

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Other vacation rentals with a kayak

Top guest favorite

The image showcases a serene beach scene framed by lush green trees. Soft sand meets gentle waves under a bright blue sky. Vibrant coastal vegetation leads to the sandy shoreline, where silhouettes of beachgoers can be seen in the distance, enjoying the tranquil setting.

Condo in Indian Shores

5 out of 5 average rating, 41 reviews

Stylish Beachfront Condo, Stunning Views

The outdoor space is highlighted by a shimmering private pool surrounded by a smooth concrete patio. Cozy lounge chairs are positioned nearby, with a hammock hanging in the shade. The tranquil house sits in the background under a colorful sunset sky.

Home in Bradenton

4.89 out of 5 average rating, 27 reviews

Coastal Haven w/pool in Bradenton

Top guest favorite

A screened-in pool area features a sparkling blue pool, surrounded by several lounge chairs in turquoise. Two umbrellas provide shade, while lush greenery is visible in the background, showcasing the tranquil waterway just beyond.

Guest suite in Bradenton

4.98 out of 5 average rating, 47 reviews

Waterfront Suite-20 min to Gulf Beaches

Top guest favorite

A shared hot tub overlooks the water, with two guests enjoying beverages while gazing at scenic views. Lush greenery frames the scene, and a variety of kayaks and paddleboards are visible in the background, enhancing the outdoor atmosphere.

Home in Indian Rocks Beach

5 out of 5 average rating, 79 reviews

Waterfront Duplex- kayaks, SUP, 3 blocks to beach

A large saltwater pool is surrounded by comfortable lounge chairs and palm trees, providing a relaxing outdoor environment. The pool area is complemented by a backdrop of the condo building, with multiple levels visible under clear blue skies.

Condo in Bradenton Beach

4.97 out of 5 average rating, 60 reviews

2 BDR, 2 Bath,Fully Loaded Condo, Largest Pool-182

The exterior of a mobile home is shown, featuring light-colored siding and a small porch. A palm tree adds tropical charm, while a well-maintained landscape is visible, including a gravel pathway and white fencing that encircles the yard.

Place to stay in Bradenton

4.98 out of 5 average rating, 48 reviews

Seas The Day By The Bay

Home in Bradenton

4.95 out of 5 average rating, 19 reviews

Private Pool + Game Room Near AMI Beach - NEW

Top guest favorite

Aerial view showcases the property surrounded by lush greenery, with water views of the Manatee River. The image captures the nearby fishing pier, outdoor spaces, and proximity to the river, emphasizing the serene landscape and natural beauty of the area.

Villa in Bradenton

5 out of 5 average rating, 59 reviews

Tranquil Tide Villa - Waterview! 15 min to beach

Quick stats about vacation rentals with a kayak near Anna Maria Island

Total rentals
80 properties
Nightly prices starting at
€ 85 before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
60 properties have a pool

Destinations to explore