Holiday rentals with a kayak in Holmes Beach

4.98 out of 5 average rating, 124 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 spacesCondition

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

ValueLocationIndoor spaces

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 )

LocationValueIndoor spaces

4.91 out of 5 average rating, 190 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.

Outdoor spacesLocationGetting around

4.95 out of 5 average rating, 209 reviews

The outdoor area showcases a well-lit private pool surrounded by tropical landscaping and palm trees. Lounge chairs are positioned by the pool, and a small blue hot tub is visible in the background, contributing to the serene ambiance of the space.

Home in Anna Maria

9/14-9/17 Discount 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.

ValueLocationSleep quality

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.

Outdoor spacesValueKitchen

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 spacesLocationAmenities

5.0 out of 5 average rating, 24 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.

LocationOutdoor spacesParks

4.96 out of 5 average rating, 128 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!

Outdoor spacesLocationPool

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.

Outdoor spacesLocationAccess

4.86 out of 5 average rating, 438 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 spacesValueView

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.

4.9 out of 5 average rating, 68 reviews

Backyard Bliss Anna Maria Island

Welcome to Backyard Bliss, where resort-style living meets premier location! With the powdered sands of the Gulf of Mexico only 500 steps away and a retreat that offers endless amenities, a stay at Backyard Bliss will guarantee a smile on your face when you’re here, and a frown when you have to leave.

LocationValueHospitality

Popular amenities for Holmes Beach kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

5.0 out of 5 average rating, 18 reviews

Casa Coquina AMI- Newly Renovated, steps to beach!

LocationOutdoor spacesCheckout

Luxe

5.0 out of 5 average rating, 10 reviews

Waterfront Home Private pool, elevator and dock

LocationOutdoor spacesDecor

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

LocationAmenitiesSleep quality

5.0 out of 5 average rating, 21 reviews

Canalfront + Heated Pool | 5 Min to AMI | Kayaks

LocationOutdoor spacesView

5.0 out of 5 average rating, 46 reviews

Home in Bradenton Beach

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

LocationOutdoor spacesCondition

4.95 out of 5 average rating, 65 reviews

Home in Anna Maria

H2O 360 by Beach Boutique Rentals

LocationValueAir conditioning

4.86 out of 5 average rating, 7 reviews

Cheerful Serenity | Pool | Dock | Sunset Views

Outdoor spacesLocationHospitality

4.78 out of 5 average rating, 40 reviews

250 steps to the Beach | Heated pool + spa

LocationValueQuiet

Cottages with a kayak

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

LocationValueKitchen

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!

LocationValueAccess

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

ValueLocationAccuracy

4.97 out of 5 average rating, 73 reviews

Cottage in Bradenton

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

Outdoor spacesLocationFamily

4.97 out of 5 average rating, 39 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

Outdoor spacesLocationComfort

4.88 out of 5 average rating, 16 reviews

Cottage in Holmes Beach

Waterfront Villa Delphina

LocationAccuracyAir conditioning

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

LocationAccuracyFamily

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

LocationWalkabilityPool

5.0 out of 5 average rating, 6 reviews

Other holiday rentals with a kayak

4.93 out of 5 average rating, 14 reviews

A sign bearing the name 'Gulf Beach Place' is prominently displayed against a backdrop of palm trees. The area is surrounded by gravel and features a white fence, indicating a welcoming entrance to the condo property.

Condo in Holmes Beach

Gulf Beach Getaway-STEPS FROM BEACH

LocationPoolQuiet

4.98 out of 5 average rating, 85 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks

LocationValueAccess

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

Outdoor spacesLocationGetting around

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, 25 reviews

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

LocationOutdoor spacesCleanliness

5.0 out of 5 average rating, 23 reviews

Home in Cortez

1918 Historic Cottage • Walk/Bike to AMI Beaches

LocationValueBeach

4.93 out of 5 average rating, 28 reviews

Home in Cortez

NEW Waterfront | Heated Pool | Kayaks

Outdoor spacesValueWalkability

5.0 out of 5 average rating, 11 reviews

Home in South Bradenton

IMG Lake & Beach Home with Pool White Sand Beaches

LocationFamilyCleanliness

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.