Holiday rentals with a kayak in Longboat Key

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.

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

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

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.

4.88 out of 5 average rating, 207 reviews

A charming cottage is set against a vibrant blue exterior, featuring a thatched umbrella over a small outdoor seating area with four chairs. Lush green shrubs and sandy pathways enhance the inviting entrance, while palm trees are visible in the background under clear blue skies.

Bungalow in Anna Maria

Bay Breeze Cottages #2

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.

4.87 out of 5 average rating, 314 reviews

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

Flat in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Huts. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Apartment 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.

4.88 out of 5 average rating, 139 reviews

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

4.97 out of 5 average rating, 234 reviews

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.

5.0 out of 5 average rating, 66 reviews

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.

Home in Anna Maria

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.

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

Luxury golfer's paradise on the water! Private canal home w/ boat + jet ski lifts, resort-style pool, spa, fire pit, putting green, swim-up bar + pergola. Minutes to top golf, IMG Academy, Benderson Park & Premier Sports Campus. Fully remodeled for the ultimate Florida escape. Ideal for tournaments, retreats, or family gatherings. Limited availability—book now to secure your stay at Bradenton’s premier waterfront rental.

4.92 out of 5 average rating, 75 reviews

Flat in Longboat Key

Renovated Beach Paradise. Ground Floor unit 64

Completely renovated. Everything is new. Amazing location. This condo has patio. Condo management will help you with your accommodation. The unit offers everything you may want and need!!! Escape to our Tropical Paradise with beautiful beach, heated pool and awesome sunsets. Beach side condo located on the first floor, just a short walk from your door to the beach and pool. No crossing the streets.

Popular amenities for kayak rentals in Longboat Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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

5.0 out of 5 average rating, 100 reviews

5.0 out of 5 average rating, 115 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

4.92 out of 5 average rating, 103 reviews

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

4.98 out of 5 average rating, 83 reviews

Home in Sarasota

Winter Haven Retreat – Steps to Bay & Ringling

5.0 out of 5 average rating, 46 reviews

Home in Bradenton Beach

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

A clear view of the pool area is presented, featuring a sparkling blue pool surrounded by sun loungers. A shaded umbrella provides relief from the sun, while the tranquil Bay stretches in the background, enhancing the serene setting.

4.94 out of 5 average rating, 47 reviews

Birds and Sunsets

A charming single-family home is depicted, featuring a light-colored exterior with a welcoming entrance and a staircase leading to the front door. Lush greenery surrounds the property, including palm trees and well-maintained grass, creating a serene outdoor setting.

5.0 out of 5 average rating, 63 reviews

Waterfront Wares Creek Cottage with dock access

4.97 out of 5 average rating, 33 reviews

Home in Cortez

Canal Retreat: Heated Pool • Dock • Kayaks • Bikes

Cottage rentals with a kayak

4.96 out of 5 average rating, 113 reviews

A screened-in pool area is presented, featuring a clear blue pool surrounded by stone pavers. Lush greenery and water views are visible through the screen, enhancing the sense of tranquility and connection with nature.

Cottage in Nokomis

New Pool Tropical Waterfront Dock & Optional Boat

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!

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

4.89 out of 5 average rating, 193 reviews

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!

4.97 out of 5 average rating, 73 reviews

Cottage in Bradenton

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

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

4.97 out of 5 average rating, 39 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

Superhost

Cottage in Holmes Beach

Waterfront Villa Delphina

Other holiday rentals with a kayak

4.83 out of 5 average rating, 64 reviews

Flat in Siesta Key

Gertrude's Siesta | Oceanview, 1-min to Beach

5.0 out of 5 average rating, 53 reviews

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.

Home in Holmes Beach

Destination Relaxation

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

Apartment in Indian Shores

Oceanfront Condo with Beach Access

4.96 out of 5 average rating, 77 reviews

Apartment in Bradenton Beach

An aerial view of a coastal condo complex showcases a well-maintained tennis court in the foreground, adjacent to a sparkling pool area. Expansive ocean views are visible in the background, highlighting the proximity to the beach. Lush palm trees provide greenery around the facilities.

Island Escape Beach Pool Hot Tub WATER VIEWS

5.0 out of 5 average rating, 7 reviews

5.0 out of 5 average rating, 6 reviews

Home in Anna Maria

Sandcastle -Steps to Beach -Pool - Golf Cart

4.98 out of 5 average rating, 47 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach