Vacation rentals with a kayak in Redington Beach

Cottage in Pass-a-Grille Beach

A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.

4.8 out of 5 average rating, 295 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Welcome to your beach getaway! This cheerful, sun-soaked cottage is steps from the sand—or your next ice cream or seaside meal at a nearby restaurant. Perfect for couples or solo travelers, a comfy queen bed, a breezy living room, and a kitchen and dining area. Sip your morning drink on the upstairs porch as salty breezes drift by, or fire up the BBQ on the downstairs patio. Two bikes are yours to cruise the island like a local—Everything you need for a relaxing, joy-filled beach escape is here

Condo in Indian Rocks Beach

A well-maintained outdoor area features a putting green surrounded by lush green turf. Comfortable lounge chairs are positioned nearby, with a table and chairs set against a backdrop of the Intracoastal waterway. A clear blue sky and vibrant foliage contribute to the serene atmosphere.

4.79 out of 5 average rating, 141 reviews

2BR: Intercoastal Views, 3 Min Walk to Beach

LUXURY AWAITS in this 2 BR/1 BA full kitchen condo with unobstructed PANORAMIC WATER VIEWS of the SPARKLING Intracoastal WATERWAY!! Just minutes to the Gulf of Mexico by BOAT or FOOT! Enjoy the SUNRISE off the PRIVATE DOCK or take a 3 minute walk to the beach to ENJOY BREATHTAKING SUNSETS!! The Intracoastal has many advantages including very calm water for: Fishing, Boating, Paddle Boarding, Kayaking, and More! We are also a 3 minute walk to pickleball, basketball, and a fenced in playground!

Townhouse in Redington Beach

A bright living area features comfortable white seating arranged around a wooden coffee table. Built-in shelves display books and decorative items. A flat-screen TV is mounted on a shiplap wall, while a dining area is visible in the background, showcasing a rustic table and modern fixtures.

4.91 out of 5 average rating, 126 reviews

Modern Townhouse right across beach! Table tennis

3 Bedroom/2.5 Bath modern townhome across street from beach, 2 large balconies off of living room and master bedroom. Lush landscaping. Enjoy meals in the beautiful dining area. Full equipped kitchen! Parking garage 1 car and driveway parking available. Sleeps 10. We rent all year round due to beautiful Florida weather. Walking distance to beach, restaurants, parks, basketball court, volleyball. Close to Johns Pass, 1 mile - Indian Rocks Beach. Tampa, Clearwater and St. Pete are a short drive.

4.9 out of 5 average rating, 138 reviews

The exterior of a three-story building is presented, featuring multiple balconies with sliding glass doors. Lush greenery is visible in the foreground, framing a pathway leading to the entrance. The structure's design showcases natural materials and a coastal aesthetic.

Condo in Indian Shores

On the Beach "Little Peace of Heaven" Beach Condo

Spacious - Complete Renovation - Come see!! Our building is on an Island and on the beach! Our unit faces East or the Inter-coastal but the beach is just downstairs. Our 8 unit building is ‘On the beach. Downstairs we have a beautiful semi-private patio area surrounded by sea grape plants. We have a table and chairs, 16 beach chairs, kayaks and paddleboards, outside shower, gas grill, & a firepit for all to enjoy. Wonderful & quiet for families & couples. No smoking in the unit. No pets.

4.99 out of 5 average rating, 154 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.97 out of 5 average rating, 149 reviews

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

Villa in Largo

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

4.89 out of 5 average rating, 133 reviews

Condo in Tampa

Tampa Bay Gem - Spectacular Beachfront Views

Escape to the tranquil shores of Rocky Point Island and bask in the awe-inspiring beauty of the ocean view. Our impeccable condo boasts stunning sunsets over Tampa Bay, perfect for a stylish getaway. Just steps away from Ben T Davis Beach and delicious restaurants, plus the Tampa Int'l Airport, Raymond James Stadium, downtown, Amalie Arena, Straz Center, Historic Ybor City, Hyde Park, Soho, Riverwalk, and the Port of Tampa. Book now for an unforgettable experience filled with adventure.

4.88 out of 5 average rating, 144 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.

Condo in Independence Square

The open-concept living area features a modern kitchen with stainless steel appliances and a granite countertop. A seating area includes a light gray sofa adorned with blue and pink pillows, and a wooden coffee table. Natural light fills the space through shuttered windows, enhancing the homey feel.

4.94 out of 5 average rating, 212 reviews

Steps from the Sand - Clean, Stylish 2-BR Condo

AQUA BEACH CONDO - Only 90 steps from the beach, this beautifully updated and perfectly located beach condo offers you the very best of Indian Rocks Beach, a charming and intimate beach town located between Clearwater and St. Pete Beach. Two bedrooms with en-suite bathrooms and large walk-in closets, as well as the lofty living area and modern open kitchen will make you feel like at home. This condo is better equipped than your average vacation rental. Continue to read for more...

Condo in Indian Rocks Beach

A shaded lounging area features a comfortable chair with a patterned cushion, facing a serene waterfront view. In the background, a dock extends into the calm water, surrounded by lush greenery and decorative plants.

4.96 out of 5 average rating, 125 reviews

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam king bed & secured safe.

5 out of 5 average rating, 147 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Apartment in Clearwater Beach

A bright and airy bedroom features a spacious bed with white linens and decorative pillows. A ceiling fan is present above, and a window with sheer curtains allows natural light to enter. A cozy seating area and a small refrigerator are visible in the room.

4.85 out of 5 average rating, 163 reviews

Stylish Waterside Studio 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! NO PETS ALLOWED IN THIS SPECIFIC UNIT.

Popular amenities for Redington Beach kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

Two lounge chairs are positioned beside a small table, offering a view of the serene canal. Tall palm trees and lush greenery frame the scene as the sky transitions with hues of purple and orange during sunset.

4.89 out of 5 average rating, 148 reviews

Azule|Waterfront | Walk to Beach-Dock-Bikes-Kayaks

4.96 out of 5 average rating, 24 reviews

Waterfront, heated pool, golf cart, kayaks & SUP

4.91 out of 5 average rating, 139 reviews

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

Home in Palm Harbor

Peaceful Pet friendly 2 BR cottage with hot tub.

4.92 out of 5 average rating, 126 reviews

A view of the beach is captured through swaying palm trees, framed by a white picket fence. Nearby, a pathway leads to the sand, while parked cars line the road. The clear blue sky complements the vibrant coastal scenery.

Home in Clearwater Beach

Cambria Beach House Clearwater Beach

4.94 out of 5 average rating, 16 reviews

Steps 2 beach/Heated Pool/In and outdoor Game Room

5 out of 5 average rating, 3 reviews

Ocean Dream Villa| Beachfront with Private Pool

4.89 out of 5 average rating, 9 reviews

An outdoor kitchen area features a grill and bar seating under bright blue umbrellas. Spacious deck space allows for unobstructed views of the waterfront, complemented by palm trees in the background. The scene is set against a clear blue sky with white, fluffy clouds.

Home in St. Petersburg

Waterfront + Heated Pool | Pet + Boat Friendly!

5 out of 5 average rating, 27 reviews

A serene waterfront view is captured at sunset, reflecting vibrant colors on the calm water. Boat docks line the banks, surrounded by lush greenery and palm trees. The peaceful atmosphere is enhanced by distant sailboats gently bobbing in the marina.

Home in Madeira Beach

Flamingo Flair & Waterfront Air — Pure Paradise!

Cottage rentals with a kayak

Cottage in Clearwater Beach

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.

4.78 out of 5 average rating, 157 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

A cozy outdoor space is framed by lush greenery and bamboo, containing several chairs arranged around a circular table. A BBQ grill is positioned against the exterior wall of the cottage, and colorful inflatables are placed nearby, creating a relaxed environment.

Cottage in Crystal Beach

4.89 out of 5 average rating, 36 reviews

Elegant Crystal Beach cottage within sea glimpse

Cottage in Pass-a-Grille Beach

A wooden boardwalk leads directly to the beach, framed by sandy dunes and swaying grass. The clear blue sky meets the calm waters of the Gulf, creating an inviting scene for beachgoers. The soft beach sand stretches out, blending seamlessly into the horizon.

4.88 out of 5 average rating, 179 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Two comfortable chairs with light cushions are positioned under a large umbrella on a wooden deck. Lush greenery, including palm trees and shrubs, surrounds the area, creating a serene outdoor space with ample natural light.

Cottage in Indian Rocks Beach

1 Bd Immaculate Gulf front BOHO Beach Cottage

Cottage in Clearwater Beach

A charming pink cottage displays a welcoming façade with colorful accents. Outdoor seating areas are present, including a swing and bicycles parked nearby. The property is surrounded by lush greenery, enhancing its beachside appeal and inviting relaxation.

4.66 out of 5 average rating, 158 reviews

Sleep 7 Steps to Beach Pets OK Real Beach Cottage

4.96 out of 5 average rating, 70 reviews

The exterior of a bright green cottage is framed by lush greenery and ornamental plants. A welcoming porch features seating arrangements, and hanging flower baskets add a touch of vibrancy. Sunlight filters through the trees, creating a cheerful and inviting entrance.

Cottage in Crystal Beach

Escondido Boutique Bungalow in Crystal Beach

4.83 out of 5 average rating, 111 reviews

A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.

Cottage in Crystal Beach

Happy Camper Cottage | Cozy Oasis with Hot Tub

Other vacation rentals with a kayak

4.95 out of 5 average rating, 40 reviews

A serene backyard oasis is presented, featuring a circular stone patio surrounded by lush tropical plants. A cozy seating area with a fire pit is visible, along with a tall blue umbrella offering shade. The view extends to a calm waterway, bordered by trees.

Home in Ozona

Casa Del Sole

Apartment in St. Petersburg

4.75 out of 5 average rating, 4 reviews

Pool, Bay View, 5 min St Pete Beach @ Sand Dollar

Apartment in Treasure Island

A modern kitchen bar area features two upholstered chairs, positioned beneath three textured pendant lights. A serene view of the canal is visible through an open window, framed by sheer curtains that gently diffuse natural light.

5 out of 5 average rating, 28 reviews

Waterfront Apartment with Dock inTreasure Island

4.71 out of 5 average rating, 24 reviews

A comfortable living area features a large sectional couch and a light-colored armchair. Natural light streams through the sliding glass doors, which open to a scenic view of palm trees and the outdoor space. A ceiling fan softly hangs overhead, and a television is mounted on the wall.

Condo in Madeira Beach

Across from Madeira Beach Gulf-View Condo Pool

5 out of 5 average rating, 11 reviews

Home in Palm Harbor

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

5 out of 5 average rating, 67 reviews

A charming outdoor area features a decorative stone floor and a tranquil fountain surrounded by lush greenery. Wicker seating offers a cozy space for relaxation, while decorative wall art adds a touch of character to the bright yellow walls.

Guesthouse in Clearwater

Charming Casita Near Two Downtowns & Beaches

Apartment in Treasure Island

A private balcony is presented with two wicker chairs and a small round table, offering expansive views of the sandy beach and ocean. The clear blue sky merges with the horizon, creating a serene coastal atmosphere.

5 out of 5 average rating, 18 reviews

Sand, Sunset, Sleep Repeat Gulf Front Condo