Holiday rentals with a kayak in Indian Shores

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, 139 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, 137 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, 143 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

4.94 out of 5 average rating, 106 reviews

A cozy camper trailer is positioned among lush greenery and bamboo, with an awning extended to provide shade. Gravel paths lead to the trailer, and various potted plants add a natural touch to the private outdoor space.

Tiny home in Coquina Key

Waterfront tiny in St Petersburg - The ‘V’

The ‘V’ is your perfect getaway to make fun memories. Note: You MUST have a 5 star rating on airbnb ! Take yourself back to the good old days of simplicity and relaxation. Paddle-board from your own private mangrove beach through the canals and to Tampa Bay. Experience dolphins swiming along side you, manatees feeding on sea grass or baby sharks out by the sandbar just 200 yards from the beach. The ‘V’ rests in a culd-de-sac in a quiet waterfront neighborhood just 10 minutes south of DT.

4.97 out of 5 average rating, 144 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, 140 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...

Houseboat in Clearwater Beach

Large sliding glass doors open to waterfront views, revealing a sunlit space with a modern kitchenette. A small dining table with two chairs is set near the doors, and a flat-screen TV is mounted on the wall, complementing the serene aquatic surroundings.

4.79 out of 5 average rating, 114 reviews

Breathtaking Beachy Houseboat on Clearwater Island

🌊 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! 🌅🏝️🚤 NO PETS ALLOWED.

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, 124 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, 146 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

4.86 out of 5 average rating, 310 reviews

An inviting balcony view overlooks a spacious pool area and the intercoastal waters, framed by palm trees. A light-filled living area features comfortable furnishings and a television, while the dining space and kitchen are visible, providing a warm atmosphere for relaxation and enjoyment.

Condo in St. Petersburg

Breathtaking Waterview & Pool View Condo

Waterfront condo with pool view. The view of the intercoastal is fantastic. Especially beautiful sunsets! Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking intercoastal or stay indoors and enjoy puzzles and games.

Popular amenities for Indian Shores kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

Home in Indian Rocks Beach

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

4.91 out of 5 average rating, 137 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.

5 out of 5 average rating, 14 reviews

The image features a serene beach scene with soft, white sands leading to gentle waves lapping against the shoreline. The clear blue water blends into shades of green, under a partly cloudy sky. People can be seen enjoying the water along the beach.

Home in Indian Shores

Beautiful Cozy Beach Home

5 out of 5 average rating, 13 reviews

Home in Largo

Southern Comfort close to Beach!

4.92 out of 5 average rating, 124 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

Home in Indian Rocks Beach

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.

5 out of 5 average rating, 85 reviews

Waterfront Duplex- kayaks, SUP, 3 blocks to beach

5 out of 5 average rating, 49 reviews

Home in Largo

Manatee Cove Waterfront | Heated Pool, Dock, Kayak

5 out of 5 average rating, 25 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!

Cottages with a kayak

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, 290 reviews

Sunny PaG Island rental w/bikes-just steps2beach

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

4.91 out of 5 average rating, 125 reviews

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

Little Manatee River Cottage

5 out of 5 average rating, 7 reviews

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

Cottage & Tree ~ by the Sea

4.96 out of 5 average rating, 45 reviews

An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.

Cottage in Bradenton

2/2 Charming Riverfront Cottage w Deck & Kayaks

4.97 out of 5 average rating, 228 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

4.84 out of 5 average rating, 107 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

4.88 out of 5 average rating, 16 reviews

A large, partially covered deck offers a view of the canal, accented by palm trees and a clear blue sky. Outdoor seating areas include a wooden rocking chair and several dining chairs, inviting relaxation by the water's edge.

Cottage in Hudson

Water Front Nautical Haven

Other holiday rentals with a kayak

5 out of 5 average rating, 15 reviews

A spacious living area features a striped, blue and white sofa set with matching armchairs. Large sliding glass doors open to a balcony, providing views of the water. A flat-screen TV is positioned on a low table, and two lamps provide soft lighting.

Condo in Sunset Beach

Land's End 11-404: Gulf Front Gem - 2BD/2BA

4.86 out of 5 average rating, 58 reviews

A cozy dining area is positioned next to expansive glass windows offering a view of the ocean. A round table with two white chairs is complemented by rustic decor, while light-colored curtains frame the scene, enhancing the openness and connection to the seaside.

Condo in Belleair Beach

Belleair Beach 215 Beachfront Gem Steps from Sand

Apartment in St. Petersburg

4.67 out of 5 average rating, 3 reviews

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

Townhouse in Indian Rocks Beach

The exterior of a modern two-story beach house is highlighted, featuring a private backyard with a heated saltwater pool. Colorful pool floats and patio umbrellas complement the inviting outdoor space. Lush palm trees and seating areas provide a relaxed atmosphere, with glass doors leading into the home.

5 out of 5 average rating, 9 reviews

Walk2Beach, Heated Pool, Pool Table/ GameRoom, PS5

4.93 out of 5 average rating, 97 reviews

A cozy living area is furnished with a light brown sofa adorned with colorful throw pillows. A wooden coffee table sits atop a patterned area rug with floral designs. A large television is mounted on the wall, and a kitchen area is visible in the background.

Condo in Indian Shores

Fabulous! Lush Views and Amenities by the beach!!

Townhouse in Redington Beach

An open-concept living area is highlighted by a large sectional sofa and a circular coffee table. Light-colored furniture complements natural wood accents, while a ceiling fan circulates air. Windows allow ample light, and a dining area is visible in the background.

5 out of 5 average rating, 4 reviews

RBV 307 - Gulf View from balcony- Hot Tub!

5 out of 5 average rating, 7 reviews

Home in Palm Harbor

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