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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, 285 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, 104 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, 149 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

4.98 out of 5 average rating, 131 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, 348 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.

The exterior of the home showcases a three-story design, featuring multiple balconies and expansive windows. A private heated pool and spa are visible in the foreground, surrounded by lush landscaping. The evening sky displays a blend of soft colors, enhancing the tranquil atmosphere.

Home in Anna Maria

5 out of 5 average rating, 4 reviews

Beach a la Mode | Luxury Anna Maria Island Home!

"Exclusive Amenities Include: • Private Heated Pool & Spa • Canal Front Access & Views • Private Rooftop w/ Incredible Water Views • 7 Minute Walk to Bayfront Park • Multiple Balcony Views w/ Loungers • 5 Bedrooms, 4.5 Baths • 2 King Beds, 2 Queen Beds & 4 Twin Beds (Sleeps 8) • Game Room • Poolside Dining Area • Outdoor Shower • Corn Hole & Ping Pong Table • Private 2 Car Garage • Free WiFi • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials"

A bright living area is shown, featuring a comfortable gray sofa with patterned throw pillows. A light-colored coffee table sits on a textured area rug. Large glass doors open to a lush backyard, which can be seen through sheer white curtains, allowing natural light to fill the space.

Home in Sarasota

4.95 out of 5 average rating, 110 reviews

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

A bright living area features a navy blue sofa paired with a circular wooden side table and a lamp. Wall art includes framed phrases and decorative elements, while light wood flooring enhances the openness. A kitchenette is visible in the background, adding to the functional design.

Vacation home in Clearwater

4.91 out of 5 average rating, 111 reviews

Coastal Waterfront Condo 2 blocks 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! 🌅🏝️🚤

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, 183 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, 144 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

The exterior of a charming yellow bungalow is visible, featuring a covered patio area with potted plants. The entrance is accessed via a set of steps leading to the upper level, while brick pavers create a welcoming pathway.

Apartment in Bradenton Beach

4.87 out of 5 average rating, 393 reviews

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

Top guest favorite

A charming exterior of a cottage is showcased, featuring a light-colored facade and a sturdy metal roof. A private patio area is visible with a blue picnic table and outdoor seating, surrounded by landscaping and palm trees, offering a relaxed outdoor space.

Guesthouse in Bradenton

4.98 out of 5 average rating, 188 reviews

Conch Cottage adorable one bedroom with pool.

Take it easy at this unique and tranquil getaway. Conch Cottage is 5 minutes to Anna Maria Island. Walk to Portosueno park and see the Manatees watch the sunset from the park or bridge. Kayak, walk or bike Robinsons Preserve. So much to do in this historic Palma Sola Neighborhood.

Popular amenities for kayak rentals near Anna Maria Island

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

A spacious private pool area is surrounded by tropical landscaping and natural stone pavers. Sun loungers are positioned along the poolside, with a refreshing water feature visible in the pool. The exterior of the home features vibrant colors, adding character to the setting.

Home in Anna Maria

5 out of 5 average rating, 24 reviews

Cedar Sunsets - 4 bed, 4 bath, 4 Houses to the Bea

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

4.89 out of 5 average rating, 19 reviews

Private House on the Ocean With Heated Pool & Doc!

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

The home's exterior is softly illuminated by warm lights, highlighting the paved driveway and tropical landscaping. Tall palm trees and lush greenery surround the entrance, creating a serene atmosphere. The modern roof adds a contemporary touch, enhancing the inviting appearance of the property.

Home in Longboat Key

4.85 out of 5 average rating, 131 reviews

Summer House longboat key

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

4.91 out of 5 average rating, 23 reviews

Coastal Haven w/pool in Bradenton

A private splash pool is surrounded by lounge chairs and umbrellas, with palm trees providing natural shade. The pool area offers views of the beach, creating a relaxing outdoor space for guests to unwind in the sun.

Home in Indian Rocks Beach

4.82 out of 5 average rating, 17 reviews

Ocean Blue Villa | Beachfront with Private Pool

A modern bayfront home is surrounded by lush greenery and mature trees. The driveway leads to a well-manicured front yard, with inviting seating areas visible near the entrance. The sleek garage door complements the stylish exterior, showcasing a blend of contemporary and natural aesthetics.

Home in St. Petersburg

5 out of 5 average rating, 4 reviews

Waterfront Luxury | Sunset Views

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

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, 154 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 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

4.92 out of 5 average rating, 120 reviews

Little Manatee River Cottage

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, 177 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, 4 reviews

Cottage & Tree ~ by the Sea

Two kayaks are mounted on a rack against a vibrant green wall. The upper kayak features a silver hull with yellow accents, while the lower kayak is bright green with a purple cushion. The structure is complemented by a dark brown door nearby.

Cottage in Sarasota

4.82 out of 5 average rating, 157 reviews

Pet friendly Cottage

Cottage in Bradenton

4.95 out of 5 average rating, 41 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

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

A spacious living area features a striped, blue and white sofa set with matching armchairs. Large sliding glass doors open to a balcony, providing views of the water. A flat-screen TV is positioned on a low table, and two lamps provide soft lighting.

Condo in Treasure Island

5 out of 5 average rating, 13 reviews

Land's End 11-404: Gulf Front Gem - 2BD/2BA

A bright and airy living space features light blue sofas and coastal decor. A television is positioned on a white entertainment unit, with views of the screened balcony visible through sliding glass doors. Potted plants add a touch of greenery to the space.

Condo in Bradenton Beach

5 out of 5 average rating, 5 reviews

Island time at Runaway Bay by A Shore Thing Vacati

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

Top guest favorite

A private deck overlooks Heron Lagoon, featuring a dining table with two chairs shaded by a large blue umbrella. Two lounge chairs sit invitingly on the deck, alongside lush greenery and trees that frame the tranquil water view.

Bungalow in Siesta Key

5 out of 5 average rating, 14 reviews

Lagoon, pool, the Ringling at Siesta Key Bungalows

Top guest favorite

The exterior of a waterfront home is visible, with a wooden dock leading to a spacious patio area. The house is painted in soft blue tones and features large windows. A cozy seating area is seen under a pergola, with a spa located to the side.

Home in Indian Rocks Beach

5 out of 5 average rating, 34 reviews

Dolphin Blue Beach House-Waterfront, Pet friendly

Home in Bradenton

5 out of 5 average rating, 13 reviews

Treehouse Fun •Waterfront • Heated Pool • Hot Tub

Top guest favorite

Condo in Bradenton

5 out of 5 average rating, 13 reviews

3/3 condo with Pool - 2 miles to beach

A pathway leads to Vista Lake, bordered by lush greenery and tropical plants. Kayaks in vibrant colors are neatly stacked, each equipped with life vests. The serene waterway is visible in the background, framed by trees and palms, enhancing the natural setting.

Condo in Anna Maria

4.89 out of 5 average rating, 9 reviews

Resort-Style Ground Floor 1-Bdr., Heated Pool/Spa

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

Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ367 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