Holiday rentals with a kayak in Bradenton

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.

ValueOutdoor spacesBathroom

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

ValueLocationBack garden

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.

Guest house 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 )

ValueOutdoor spacesAccess

4.97 out of 5 average rating, 73 reviews

Cottage in Bradenton

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

Old Florida charm meets peaceful riverfront living at the Lazy Gator Lodge. This unique Braden River getaway features two spacious king en suite bedrooms, an open-concept living area, fully stocked kitchen, massive waterfront deck, & fenced yard perfect for pets. Guests can explore the river by kayak and paddle to local waterfront restaurants and live music spots. Centrally located near Lakewood Ranch, UTC, Bradenton and Sarasota — plus the white sand beaches of Siesta Key & Anna Maria Island.

LocationOutdoor spacesGrill

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!

Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all

LocationOutdoor spacesLong stay

5.0 out of 5 average rating, 115 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

Outdoor spacesLocationAmenities

4.79 out of 5 average rating, 106 reviews

Endless Summer Escape - Amazing Heated Pool/Spa

This tropical retreat is loaded with charm. The backyard is your own private resort featuring a massive and amazing heated pool and spa, modern outdoor shower, plenty of seating & dining space, & quaint courtyard with a fire pit. The spacious and modern home has 2 living spaces and over 2100 square feet. Each bedroom has it's own private bathroom! Located just 5 miles from the beautiful beaches of Anna Maria Island but even closer to beautiful parks for biking, walking, & stunning sunsets.

Outdoor spacesValueIndoor spaces

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.

ValueLocationHospitality

4.95 out of 5 average rating, 210 reviews

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

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.

Outdoor spacesLocationGrill

4.92 out of 5 average rating, 103 reviews

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

BNB Breeze Presents: Sea Gem → Welcome to your private slice of paradise—a stunning waterfront retreat. Designed for unforgettable days under the Florida sun, this home blends comfort, style, and nature. - Private dock with string lights - Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st - Rooftop deck with sweeping views - Kayaks and paddleboards for adventures - Outdoor kitchen with grill and wine cooler - Peaceful dolphin sightings from your backyard

ValueLocationCheckout

5.0 out of 5 average rating, 125 reviews

River House with Kayaks. Relax on the River.

Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.

ValueOutdoor spacesLong stay

4.86 out of 5 average rating, 439 reviews

Flat 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.

Outdoor spacesLocationLayout

Popular amenities for kayak rentals in Bradenton

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The exterior of the house features a large anchor adorned with a thick rope, surrounded by decorative stones. Lush greenery and tropical plants frame the entrance, while a red door invites guests inside. A bicycle leans against the wall, adding a casual touch.

4.93 out of 5 average rating, 110 reviews

Waterfront Home w/ Private Dock, Kayaks, and Yard!

LocationValueLaundry

4.97 out of 5 average rating, 33 reviews

Home in Cortez

Canal Retreat: Heated Pool • Dock • Kayaks • Bikes

LocationValueCondition

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

LocationOutdoor spacesAccuracy

5.0 out of 5 average rating, 11 reviews

Home in South Bradenton

IMG Lake & Beach Home with Pool White Sand Beaches

LocationComfortCleanliness

A private pool area is enclosed by a screened lanai, featuring a white water slide extending from one side. Sun loungers are positioned nearby on the patio, with lush greenery visible in the background. The pool is surrounded by a spacious deck, inviting swimming and relaxation.

4.97 out of 5 average rating, 29 reviews

Sport & Wellness Getaways

LocationValueCheck-in

4.97 out of 5 average rating, 64 reviews

Family Fun Heated Pool, Games, Crib, Peloton

ValueLocationAir conditioning

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

LocationBathroomAccuracy

4.92 out of 5 average rating, 36 reviews

Family Fun Waterfront | Pool, Kayaks & Hot Tub

ValueOutdoor spacesHot tub

Cottage rentals with a kayak

4.94 out of 5 average rating, 100 reviews

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

Coco’s Cottage FALL fun! 10% off Book by 10/1!

Outdoor spacesValueHospitality

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!

ValueOutdoor spacesBiking

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

ValueOutdoor spacesNearby

4.89 out of 5 average rating, 193 reviews

4.93 out of 5 average rating, 29 reviews

A cozy deck is featured with two chairs and a hammock, overlooking the peaceful landscape. Strings of lights enhance the space, while the sky transitions from blue to dusk. Nearby, views of open fields can be seen, creating a tranquil outdoor retreat.

Cottage in Myakka City

New Country Cottage on Lake Manatee Lakewood Ranch

Outdoor spacesLocationRiver

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

Outdoor spacesLocationNearby

4.8 out of 5 average rating, 84 reviews

Cottage in Anna Maria

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

LocationOutdoor spacesAccess

4.97 out of 5 average rating, 39 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

LocationOutdoor spacesBiking

Cottage in Holmes Beach

Waterfront Villa Delphina

LocationComfortCondition

Other holiday rentals with a kayak

5.0 out of 5 average rating, 86 reviews

An aerial view showcases the studio villa nestled among lush greenery, with the expansive Manatee River visible in the background. The nearby dock and boardwalk line the water, providing access to recreational activities, while the vibrant greenery enhances the serene outdoor atmosphere.

Villa in Bradenton

Sunswept Villa 4 - Waterview! 15 min to AMI beach

Outdoor spacesLocationHospitality

4.98 out of 5 average rating, 86 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks

ValueLocationView

5.0 out of 5 average rating, 42 reviews

A two-story home is visible across the calm waters, featuring a covered balcony with railings and palm trees adorning the front yard. A dock extends into the water, accommodating a watercraft and offering access to the bay.

Flat in Palmetto

Waterfront Studio relax, work on Snead Island, Fl.

ValueLocationWifi

4.87 out of 5 average rating, 79 reviews

A vibrant treehouse is situated within a lush backyard, featuring bright red railings, a green slide, and swings. The structure is surrounded by greenery and large Live Oak trees, providing a playful space for children to enjoy outdoor activities.

Home in Palmetto

Tranquil Retreat with Treehouse

ValueOutdoor spacesLong stay

5.0 out of 5 average rating, 21 reviews

Canalfront + Heated Pool | 5 Min to AMI | Kayaks

Outdoor spacesLocationBack garden

4.88 out of 5 average rating, 34 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

ValueLocationCleanliness

5.0 out of 5 average rating, 10 reviews

Home in Cortez

The Lazy Turtle ~ Canal-Front Retreat

LocationOutdoor spacesLayout

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.