Vacation rentals with a kayak in Anna Maria

4.98 out of 5 average rating, 125 reviews

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

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.

Outdoor spacesLocationBathroom

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 123 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

LocationValueAccuracy

4.91 out of 5 average rating, 191 reviews

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

Home in St. Petersburg

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

ValueLocationBiking

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.

4.95 out of 5 average rating, 210 reviews

Private 30’ Pool &Boat Dock & Only Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

ValueLocationBathroom

4.84 out of 5 average rating, 211 reviews

Bungalow in Anna Maria

Bay Breeze Cottages #3

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

ValueOutdoor spacesFamily

5.0 out of 5 average rating, 6 reviews

Sandcastle -Steps to Beach -Pool - Golf Cart

Escape to Sandcastle, a stunning Anna Maria Island house with breathtaking beach and water views! This family-friendly retreat boasts a private pool, is steps from the beach, and offers luxurious amenities like a complimentary 6-passenger Golf Cart, BBQ grill, and bikes. Enjoy the perfect blend of relaxation and adventure, with nearby attractions and experiences to create unforgettable memories. Perfect for families, offering a comfortable and memorable vacation experience.

LocationValueHospitality

4.88 out of 5 average rating, 139 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

Outdoor spacesValuePool

5.0 out of 5 average rating, 24 reviews

Home in Holmes Beach

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to The Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to Anna Maria Island’s white-sand beaches, this bright and beautifully designed home features a private backyard oasis with a covered pergola, outdoor lounge and dining areas, Smart TV, grill and space to soak up the Florida sunshine. Close to restaurants, shops, the free island trolley, and nearby bike and golf cart rentals.

Outdoor spacesLocationSleep quality

A serene canal view is presented, showcasing calm water reflecting vibrant hues of sunset. Lush palm trees and greenery border the serene setting, complemented by a wooden dock extending into the water. The peaceful ambiance invites relaxation and enjoyment of nature.

5.0 out of 5 average rating, 66 reviews

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

Welcome to Heavenly Hideaway, a beautiful canal-front vacation home located just a few blocks from the beach. With 3 bedrooms and 3 bathrooms, this home is perfect for families and friends seeking an unforgettable getaway on Anna Maria Island. This retreat offers luxury and comfort, close to attractions, shops, and dining. Enjoy a serene outdoor oasis with a private heated pool, a private dock on a canal, and a fire pit for smores.

LocationOutdoor spacesAir conditioning

5.0 out of 5 average rating, 70 reviews

My Mistress by Beach Boutique Rentals

*Features include* * Huge backyard with private pool and hot tub * Canal front * 3 bedrooms, 3 full bathrooms * 2 master king suites * Fun bunk bedroom for the family * Washer and dryer * Massive outdoor space with loungers and Adirondack chairs * Gas grill and gazebo * Patio dining table for 6 * Walkable to beach and bay * Dog Friendly!

LocationOutdoor spacesGetting around

Apartment in Bradenton Beach

Las Palmas Beach Rentals unit 2

Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.

LocationOutdoor spacesAir conditioning

4.86 out of 5 average rating, 439 reviews

4.82 out of 5 average rating, 119 reviews

Home in Bradenton Beach

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

AMI's Sunset Beach part of 7 miles of white sand beaches! • 200+ five-star ratings over all sites! • Gulf-views inside home. • Decks with views of Beach + Gulf + Pool. • Heated Pool with sun shelf. • Paddleboard + Kayak + Firepit + Patio + Grill. • High-speed WiFi. • Top floor of duplex. • Central location next to Sunset Beach.

Outdoor spacesValueParking

Popular amenities for Anna Maria kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.92 out of 5 average rating, 103 reviews

Sea Gem | Waterfront Oasis w/ Pool, Dock + Kayaks

LocationValueAccess

4.92 out of 5 average rating, 124 reviews

A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.

Home in Sarasota

Heated Pool - Just 1 mile to Beach! Updated/Fun!

ValueLocationWifi

Home in Indian Rocks Beach

A spacious living area features a large sectional sofa, complemented by decorative tables and potted plants. Expansive windows provide views of the water and outdoor seating, while natural light brightens the modern, open layout.

Walk to Beach! Waterfront Lux Retreat w/Kayaks

Outdoor spacesValueWifi

5.0 out of 5 average rating, 100 reviews

5.0 out of 5 average rating, 29 reviews

Home in Treasure Island

Waterfront Condo with Boat Slip & Fishing Dock

LocationOutdoor spacesFamily

A well-appointed outdoor area features an expansive heated pool with a vibrant blue hue, surrounded by stylish loungers and an outdoor dining space. Soft lighting highlights the sleek architecture of the home in the background, with lush greenery enhancing the atmosphere.

4.96 out of 5 average rating, 26 reviews

Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn

Outdoor spacesLocationAccess

5.0 out of 5 average rating, 46 reviews

Home in Bradenton Beach

Gorgeous 4BR w/Htd Pool | Walk 2 Beach | Boat Dock

Outdoor spacesLocationQuiet

4.98 out of 5 average rating, 40 reviews

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 Cortez

“Topside” luxury home in Cortez Village

LocationQuietCleanliness

4.97 out of 5 average rating, 33 reviews

Home in Cortez

Canal Retreat: Heated Pool • Dock • Kayaks • Bikes

Outdoor spacesValuePool

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

LocationOutdoor spacesWifi

4.89 out of 5 average rating, 193 reviews

4.91 out of 5 average rating, 208 reviews

A sunken living room is seen, featuring a gray sectional sofa and a blue sofa. A coffee table sits between them, complemented by a unique side table. A television is positioned on a stand opposite the sofas, with light streaming through the window-covered double doors.

Cottage in Siesta Key

Siesta Key Cozy Cottage across from the beach!

Outdoor spacesValueCheck-in

4.97 out of 5 average rating, 73 reviews

Cottage in Bradenton

River Cottage 2/2 - Kayaks & Huge Deck-Old Florida

LocationOutdoor spacesKitchen

4.74 out of 5 average rating, 137 reviews

A well-maintained garden path is lined with pavers. A wooden fence encloses the area, with lush greenery and palm trees visible in the background. A vibrant blue gate is situated along the pathway, creating a focal point amid the natural surroundings.

Cottage in Terra Ceia

Serene Island Cottage Waterfront Haven

LocationOutdoor spacesCleanliness

4.8 out of 5 average rating, 84 reviews

Cottage in Anna Maria

Sea Whisper: North End Gem w/ Pool & Boat Dock

ValueLocationBiking

4.97 out of 5 average rating, 39 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

LocationOutdoor spacesBeach

4.88 out of 5 average rating, 16 reviews

Cottage in Holmes Beach

Waterfront Villa Delphina

LocationConditionBeach

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

Anna Maria Cottage w/Golf Cart

LocationKitchenFamily

Other vacation rentals with a kayak

4.98 out of 5 average rating, 86 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks

LocationValueParking

5.0 out of 5 average rating, 23 reviews

Home in Cortez

1918 Historic Cottage • Walk/Bike to AMI Beaches

Outdoor spacesLocationFamily

4.96 out of 5 average rating, 77 reviews

Condo in Indian Shores

Oceanfront Condo with Beach Access

Outdoor spacesValueHospitality

5.0 out of 5 average rating, 3 reviews

Hangin’ on Hammock – Canalfront Pool Home

Outdoor spacesLocationFamily

4.99 out of 5 average rating, 87 reviews

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

Oceanfront · Steps to Sand · Free Kayaks

Outdoor spacesLocationComfort

4.94 out of 5 average rating, 94 reviews

Near AMI | Pool, Hot Tub, 3 Kings | Sleeps 12

ValueLocationNearby

5.0 out of 5 average rating, 31 reviews

A sparkling resort-style pool is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. A patio area with shaded seating is visible in the background, along with the steps leading to a building. The clear blue water invites relaxation and leisure.

Condo in Bradenton

Margaritaville Resort 3BR | Pool | Anna Maria

LocationOutdoor spacesCheck-in