Vacation rentals with a kayak near Bean Point Beach

4.98 out of 5 average rating, 122 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 seating is provided with two teal adirondack chairs facing a serene canal. Soft lighting from string lights illuminates the wooden deck, creating a calming environment. Lush greenery in a white planter enhances the tranquil setting by the water.

4.82 out of 5 average rating, 28 reviews

Manatee Retreat A

Escape to your own slice of paradise. Perfectly situated on a peaceful canal, one block from the sugar white sand beach, shopping & restaurants. With 3 spacious bedrooms, 2 full baths, and a pull-out sofa, the home comfortably accommodates families & groups. Start your mornings with coffee overlooking the tranquil canal, spend your days soaking up the Florida sun, and unwind in the evenings with the beautiful island sunsets. Available to rent upon arrival - 2 bikes (not e-bikes), & 3 kayaks.

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, 122 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

4.94 out of 5 average rating, 126 reviews

A heated swimming pool, shaped organically, is nestled within a screened enclosure, providing a serene escape. Surrounding planters filled with vibrant flowers add color to the outdoor space, while comfortable lounge seating creates an inviting area for relaxation.

Guesthouse in Bradenton

Near Anna Maria Island Beach-Studio on Wares Creek

This place delivers ample living space,latest amenities, and quick,easy access to Coastal Water,Anna Maria Island Beaches,and city Down Town. Spacious,bright,and tastefully furnished,with great screened porch,cozy gazebo,sparkling heated swimming pool . We supply 2 kayaks and everything that you might need to spend a day at the beach or on the water.We also supply fishing rods(adults and kids) and bait bucket. We can take you on a coastal trip in our boat if you wish (extra charges will apply )

4.91 out of 5 average rating, 208 reviews

The image displays a serene pool area with clear water reflecting sunlight. Lush greenery and palm trees frame the space, while a view of the ocean is visible in the background. Sun loungers are arranged around the pool, inviting relaxation.

Condo in Tierra Verde

Charming 2BR Condo Near Ft. De Soto

Come enjoy your next vacation, holiday, or winter escape in Tierra Verde, Florida! Watch the sun rise over Boca Ciega bay from the balcony of this beautiful, updated first floor condo. This 2 bedroom/2 full bath unit has been thoughtfully designed and furnished with everything you need to enjoy an stress-free get-a-way that feels like home. This rental has an official Certificate of Use through Pinellas County as a Short Term Rental as well as a rental license through the state of Florida.

4.9 out of 5 average rating, 187 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.

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, 207 reviews

Sunshine Cottage: 30’ Pool & Dock, 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.

4.84 out of 5 average rating, 207 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.

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.

5.0 out of 5 average rating, 23 reviews

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.

4.96 out of 5 average rating, 127 reviews

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

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!

Superhost

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.

4.86 out of 5 average rating, 438 reviews

Popular amenities for kayak rentals near Bean Point Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 113 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

An inviting hot tub with vibrant blue lighting is framed by wooden beams, creating a sheltered space for relaxation. The heated saltwater pool is visible in the background, surrounded by lush greenery and a white fence, enhancing the tranquil atmosphere.

4.89 out of 5 average rating, 66 reviews

Backyard Bliss Anna Maria Island

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, 65 reviews

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

4.97 out of 5 average rating, 37 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

A vibrant blue house is surrounded by lush greenery, featuring a spacious front deck with a covered area. The yard includes a large tree and decorative stone edging, with kayaks visible nearby. The scene captures a bright and inviting outdoor atmosphere.

5.0 out of 5 average rating, 50 reviews

Destination Relaxation

5.0 out of 5 average rating, 69 reviews

My Mistress by Beach Boutique Rentals

5.0 out of 5 average rating, 37 reviews

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

5.0 out of 5 average rating, 22 reviews

Home in Cortez

1918 Historic Cottage • Walk/Bike to AMI Beaches

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

4.89 out of 5 average rating, 193 reviews

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

Superhost

Cottage in Anna Maria

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

4.8 out of 5 average rating, 83 reviews

4.97 out of 5 average rating, 71 reviews

Cottage in Bradenton

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

Superhost

Cottage in Holmes Beach

Waterfront Villa Delphina

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

4.87 out of 5 average rating, 15 reviews

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

Steps To The Beach, Private & Heated Pool, Renovat

5.0 out of 5 average rating, 6 reviews

4.96 out of 5 average rating, 80 reviews

A narrow garden path is bordered by vibrant pink bougainvillea that arches overhead, creating a colorful canopy. The ground is scattered with fallen petals, and a wooden fence is visible in the background, contributing to a serene and inviting ambiance.

Cottage in Sarasota

Cottage by the Bay - free charging, Level 2 EV

Other vacation rentals with a kayak

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

4.98 out of 5 average rating, 84 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks

4.94 out of 5 average rating, 93 reviews

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

5.0 out of 5 average rating, 18 reviews

NEW Canal Family Home - Pool, Kayaks, Game Room

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.

4.91 out of 5 average rating, 55 reviews

4BR, Heated Pool, Pickleball, Basketball near IMG

Luxe

5.0 out of 5 average rating, 10 reviews

Waterfront Home Private pool, elevator and dock

4.88 out of 5 average rating, 33 reviews

The outdoor area features a private pool surrounded by palm trees and lounge chairs. Two large umbrellas provide shade, while a hot tub is adjacent to the pool. Colorful tiles outline the pool, enhancing the tranquil setting. A barbecue grill is visible to the side.

Home in Palmetto

Waterfront, Boat Dock, Kayaks, Fishing, Pool, Spa