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Vacation rentals with a kayak in Holmes Beach

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Top-rated kayak rentals in Holmes Beach

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Top guest favorite

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

4.98 out of 5 average rating, 104 reviews

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.

An elegant outdoor space features a heated pool surrounded by stylish stone pavers and tropical landscaping. Large covered porches provide shaded seating areas with colorful furniture, while palm trees enhance the inviting atmosphere of the home's exterior.

Home in Bradenton

4.95 out of 5 average rating, 150 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.

Home in Bradenton

4.79 out of 5 average rating, 349 reviews

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

A private heated pool is surrounded by a spacious patio, offering views of the bay. Lounge chairs are positioned nearby for relaxation. The shimmering water reflects the clear blue sky, creating a serene atmosphere for outdoor enjoyment.

Home in Holmes Beach

4.94 out of 5 average rating, 63 reviews

Bayfront Gem Pool, Spa & walk to Anna Maria Beach

Gorgeous home with direct bay views! Lounge in the private heated pool. Enjoy morning coffee while watching sunrises. Walk across the street to the beach to enjoy swimming in the most amazing water. Dock can accommodate large boats "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." VRC21-000105

Top guest favorite

A waterfront single-family home is depicted, featuring a spacious backyard with lush greenery. A private dock is visible, equipped with a boat lift. The home's screened porch offers a cozy outdoor area, while the surrounding trees provide shade and a natural setting.

Home in Riverview

4.97 out of 5 average rating, 147 reviews

Beautiful Waterfront Home on the Alafia River.

Beautiful Waterfront Single Family home on the Alafia River leading to Tampa Bay and the Gulf of Mexico. Bring your boats, jetskis, Kayaks, water toys, fishing rods, etc. Riverview Civic Center and Boat Ramp is literally a couple of blocks away from the property and trailer parking is available at the property. If it’s your lucky day, you will see manatees, dolphins, snook, redfish and stingrays right from the dock. Excellent fishing, restaurants and nightlife all on the river or by vehicle.

A wooden boardwalk leads directly to the beach, surrounded by tall grasses and lush palm trees. The serene ocean view features calm waters under a clear blue sky, with a beach access sign visible in the distance. The sandy pathway is inviting and well-maintained.

Townhouse in Pass-a-Grille Beach

4.89 out of 5 average rating, 232 reviews

Steps to Beach+bikes VaCay getaway on PaG island

Escape to charming Pass-a-Grille BeachHouse—your perfect beach getaway! Steps from Florida’s most beautiful beach, this cozy coastal retreat features hardwood floors, a beach wagon, smart TV's (also in bedroom) w/sports package, a sun patio, 2 bikes to explore. Soak up the old Florida charm and island vibes in this peaceful slice of paradise. This delightful one-bed -bath town-home style rental is situated steps away from the beautiful white sand beach that stretches for 7 miles.

A living area features a plush blue sofa and matching lounge chair, placed on a light blue and white striped rug. Large sliding glass doors open to a balcony, allowing natural light to illuminate the space. A coffee table and a side table complete the inviting setup.

Townhouse in Ruskin

4.94 out of 5 average rating, 233 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

A living area features a navy blue sofa and wooden coffee table, with a decorative fish wall art and plants adding a coastal touch. A television is situated on a sleek white console. Light wood flooring enhances the spacious feel, complemented by a welcoming 'Welcome' sign.

Vacation home in Clearwater Beach

4.87 out of 5 average rating, 148 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

Top guest favorite

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

4.95 out of 5 average rating, 183 reviews

Discounted September and October Stays w/Dock-Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

The exterior of a charming yellow bungalow is visible, featuring a covered patio area with potted plants. The entrance is accessed via a set of steps leading to the upper level, while brick pavers create a welcoming pathway.

Apartment in Bradenton Beach

4.87 out of 5 average rating, 394 reviews

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

An aerial view captures a lush backyard featuring a private heated saltwater pool and a unique 9-hole putt-putt course. Surrounding greenery enhances the inviting space, while a cozy gazebo provides a relaxing area. The overall ambiance is family-friendly and suitable for outdoor activities.

Home in Anna Maria

4.76 out of 5 average rating, 29 reviews

Sand Trap by Beach Boutique Rentals

*Features include* * Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Gas grill and outdoor dining * Huge front porch with water view! * Elevated home (requires stairs) * 4 Bali inspired bedrooms and 4 bathrooms * Bay beach directly across the street with no houses between * Steps to Pine Avenue * Beach chairs, umbrella and cart * Dog-friendly!

Top guest favorite

A contemporary studio features a queen-size bed with a light gray quilt and coordinated pillows. A small desk and chair are set beside the window with blue curtains, while decorative wall art of moons adorns the gray walls. A ceiling fan adds to the room's comfort.

Guest suite in North Hyde Park

4.96 out of 5 average rating, 104 reviews

Chic NoHo Studio 4-mins To Downtown

Location, Location, Location!! Come live like a local in one of the trendiest districts in Tampa, North Hyde Park. Be in the heart of it all with close proximity to most of Tampa top attractions. Downtown 1.1 mi, Armature Works 1.4 mi, Tampa Bay Riverwalk 1.1 mi, Raymond James 3.3 mi, TPA International 5.4 mi, Busch Gardens 11 mi, Ben T Davis Beach 7.9mi.

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Popular amenities for Holmes Beach kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

A screened-in pool area is visible, featuring a refreshing swimming pool surrounded by comfortable lounge chairs. Sun loungers are positioned around the pool, with soft towels folded on some. Lush greenery and nearby palm trees enhance the relaxing outdoor atmosphere.

Home in Bradenton

4.92 out of 5 average rating, 12 reviews

Kayak + Canal View | Next to Anna Maria & Reserve

Top guest favorite

Home in Indian Rocks Beach

5 out of 5 average rating, 38 reviews

Waterfront | King Bds | Htd Pool | BBQ | 2 Kayaks

Top guest favorite

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.

Home in Bradenton

4.97 out of 5 average rating, 89 reviews

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

Top guest favorite

A scenic view from a spacious balcony showcases the tranquil waters of the Manatee River. Comfortable white Adirondack chairs are positioned for relaxation, overlooking a heated pool and the glistening water, with lush greenery lining the waterfront.

Home in Ellenton

5 out of 5 average rating, 44 reviews

The Pink Riverhouse- Waterfront Paradise

An outdoor patio area features a large wooden table surrounded by benches. Lush greenery and potted plants add to the environment. A spacious pool is visible in the background, enhanced by partially shaded areas provided by the roof overhead.

Home in Ellenton

4.93 out of 5 average rating, 29 reviews

Waterfront Oasis

A private splash pool is surrounded by lounge chairs and umbrellas, with palm trees providing natural shade. The pool area offers views of the beach, creating a relaxing outdoor space for guests to unwind in the sun.

Home in Indian Rocks Beach

4.83 out of 5 average rating, 18 reviews

Ocean Blue Villa | Beachfront with Private Pool

A serene outdoor space is featured, showcasing a circular arrangement of Adirondack chairs surrounding a fire pit. Soft string lights illuminate the area, with a hammock positioned nearby. The backdrop includes the water, a boat dock, and trees under a colorful sunset sky.

4.91 out of 5 average rating, 187 reviews

Luxurious "Riverfront Oasis" - Waterfront w/pool

Home in Bradenton

5 out of 5 average rating, 14 reviews

Treehouse Fun •Waterfront • Heated Pool • Hot Tub

Cottage rentals with a kayak

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

Cottage in Clearwater Beach

4.77 out of 5 average rating, 154 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

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

4.9 out of 5 average rating, 10 reviews

Anna Maria Cottage w/Golf Cart

The cottage exterior features a light blue facade with a centered front door, flanked by two large windows. A small porch with a bench is present, along with potted plants. A single-car garage is visible, and a manicured lawn surrounds the home.

Cottage in Sarasota

5 out of 5 average rating, 4 reviews

Cottage & Tree ~ by the Sea

The entrance of the cottage is shown, highlighted by a well-lit walkway lined with stones. The well-maintained outdoor space features small shrubs and a wooden deck adorned with a railing, leading to the inviting front door, which is flanked by vibrant accents.

Cottage in Myakka City

4.92 out of 5 average rating, 13 reviews

New Country Cottage on Lake Manatee Lakewood Ranch

Cottage in Bradenton

4.95 out of 5 average rating, 43 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Top guest favorite

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

4.93 out of 5 average rating, 87 reviews

Alafia River Cottage

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

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

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

4.96 out of 5 average rating, 78 reviews

Cottage by the Bay - free charging, Level 2 EV

Other vacation rentals with a kayak

Two vibrant green kayaks rest on a stone patio by a serene waterway, surrounded by lush greenery. The area features a fire pit and is bordered by trees, creating a tranquil setting for outdoor enjoyment.

Home in Bradenton

5 out of 5 average rating, 30 reviews

Waterfront/Kayak with Manatees/Pool/Fish

A screened-in patio surrounds a clear swimming pool, offering views of a serene waterfront. Comfortable lounge chairs line the poolside, complemented by palm trees in the background. The tranquil setting is enhanced by the inviting blue hues of the water.

Home in Bradenton

4.9 out of 5 average rating, 20 reviews

Oceanside 3BR with Private Pool & Boat Lift

A bright and airy living space features light blue sofas and coastal decor. A television is positioned on a white entertainment unit, with views of the screened balcony visible through sliding glass doors. Potted plants add a touch of greenery to the space.

Condo in Bradenton Beach

5 out of 5 average rating, 5 reviews

Island time at Runaway Bay by A Shore Thing Vacati

Top guest favorite

A screened-in pool area features a sparkling blue pool, surrounded by several lounge chairs in turquoise. Two umbrellas provide shade, while lush greenery is visible in the background, showcasing the tranquil waterway just beyond.

Guest suite in Bradenton

4.98 out of 5 average rating, 47 reviews

Waterfront Suite-20 min to Gulf Beaches

Top guest favorite

A shared hot tub overlooks the water, with two guests enjoying beverages while gazing at scenic views. Lush greenery frames the scene, and a variety of kayaks and paddleboards are visible in the background, enhancing the outdoor atmosphere.

Home in Indian Rocks Beach

5 out of 5 average rating, 77 reviews

Waterfront Duplex- kayaks, SUP, 3 blocks to beach

A resort-style pool is illuminated at night, showcasing vibrant blue and purple hues. A round, heated spa is visible to the side, surrounded by lush tropical vegetation. Several lounge chairs are positioned near the pool, and a large umbrella provides shade.

Home in Bradenton Beach

4.85 out of 5 average rating, 46 reviews

AMI Cortez Beach Retreat "Views" Resort-style Pool

A large saltwater pool is surrounded by comfortable lounge chairs and palm trees, providing a relaxing outdoor environment. The pool area is complemented by a backdrop of the condo building, with multiple levels visible under clear blue skies.

Condo in Bradenton Beach

4.97 out of 5 average rating, 60 reviews

2 BDR, 2 Bath,Fully Loaded Condo, Largest Pool-182

Top guest favorite

Home in Indian Rocks Beach

5 out of 5 average rating, 35 reviews

Dolphin Blue Beach House-Waterfront, Pet friendly

Quick stats about vacation rentals with a kayak in Holmes Beach

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
420 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi

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