Holiday rentals with a kayak in Indian Shores

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.

4.92 out of 5 average rating, 132 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.

LocationValueDecor

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.

4.9 out of 5 average rating, 147 reviews

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.

LocationOutdoor spacesView

4.95 out of 5 average rating, 198 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

Outdoor spacesLocationTV

Condo in Indian Rocks Beach

An aerial view captures the Aqua Beach Condo location, highlighting proximity to both the Intracoastal Waterway and the beach. Lush greenery and the vibrant blue waters contrast with the nearby buildings, while the sandy shoreline stretches along the coast under a clear sky.

4.95 out of 5 average rating, 229 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...

ValueOutdoor spacesKitchen

A balcony view captures the sandy beach and turquoise waters, framed by lush greenery below. A few individuals can be seen enjoying the coastline, with palm trees providing shade. The clear blue sky complements the inviting seaside atmosphere.

4.9 out of 5 average rating, 165 reviews

Surfside Villas - Apartment B

Imagine waking up just steps from soft, sandy beaches and sparkling Gulf waters -- that's exactly what awaits at Surfside villas. Spectacular location right on Indian Shores Beach, you can stroll along the shore, watch stunning sunsets from your balcony, or simply unwind with the sound of the waves. Comfort & Convenience: The open-plan condo features a fully equipped kitchen, washer/dryer, and free on-site parking -- giving you all the comforts of home during your vacation.

ValueOutdoor spacesAir conditioning

4.96 out of 5 average rating, 141 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

Outdoor spacesValueQuiet

Apartment in Indian Rocks Beach

5.0 out of 5 average rating, 113 reviews

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

☀ Bay View Duplex ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music

ValueOutdoor spacesCondition

4.99 out of 5 average rating, 108 reviews

80’s Paradise golf cart, rooftop deck heated pool

BTR 1802 Enjoy gorgeous Florida sunrises and sunsets atop this modern executive home across from Indian Rocks beautiful nature preserve and minutes from its white sand Gulf beaches on a 6-person golf cart. The home has 4 large bedrooms and three bathrooms for larger parties. There are two bedrooms upstairs and two downstairs making this house perfect for two families or multiple couples. Kayaks are included and can be launched at the nature preserve.

Outdoor spacesLocationCleanliness

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.

4.97 out of 5 average rating, 231 reviews

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

Outdoor spacesValueCheck-in

A spacious living area features a comfortable brown sectional sofa adorned with patterned cushions. A round coffee table sits at the center. Natural light fills the room through large glass doors leading to a balcony. A cozy hanging chair and a dining area with bar stools are visible in the background.

4.92 out of 5 average rating, 125 reviews

Beautiful boho 2br townhome- pool, walk to beach!

Escape to comfort in this relaxing beach-style townhome, located in beautiful Indian Shores. This spacious townhome has all the amenities needed for a relaxing vacation for family, friends or a romantic getaway- just 2 min from beach access. Spacious renovated heated pool, and intercostal access for dolphin watching or kayaking ! Bike or walk to many shops and restaurants. The townhome is fully stocked so all you have to bring is yourself !

LocationOutdoor spacesIndoor spaces

4.76 out of 5 average rating, 211 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

ValueLocationView

5.0 out of 5 average rating, 169 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

LocationOutdoor spacesBackyard

Popular amenities for Indian Shores kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.9 out of 5 average rating, 183 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

LocationValueBarbecue

4.96 out of 5 average rating, 114 reviews

Home in St. Petersburg

Lux Mid-Century Downtown Courtyard+Parking

Outdoor spacesValueBiking

4.83 out of 5 average rating, 131 reviews

A spacious pool area features a heated saltwater pool and a hot tub surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a grill is visible, providing an inviting outdoor space. The screened enclosure offers a sense of privacy and comfort.

Home in Belleair Bluffs

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

ValueLocationCheckout

4.91 out of 5 average rating, 171 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.

LocationValueAmenities

4.96 out of 5 average rating, 131 reviews

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

Home in Dunedin

Heated saltwater pool|Spacious 4BR/3BA|

ValueOutdoor spacesLaundry

4.82 out of 5 average rating, 101 reviews

A spacious living area features large windows allowing natural light to fill the room. Two dark blue armchairs with yellow cushions face a light-colored TV stand. A cream ottoman adds comfort, while a patterned area rug anchors the space. Decorative shelves hold books and plants.

Home in St. Petersburg

Historic Charm - Great location!

ValueOutdoor spacesBeach

5.0 out of 5 average rating, 7 reviews

Waterfront Home Golf Cart Walk to Beach

LocationAmenitiesHot tub

An open-concept living area is visible, featuring modern furnishings and large windows that offer views of the intercoastal. A dining table is accompanied by blue upholstered chairs, while a comfortable seating area with a light-colored sofa and decorative plants completes the inviting space.

5.0 out of 5 average rating, 33 reviews

Waterfront 3/3 Home 3 Blocks to the Beach!

Outdoor spacesValueKitchen

Cottages with a kayak

Cottage in Pass-a-Grille Beach

4.89 out of 5 average rating, 192 reviews

Steps2Beach-Walk everywhere-Bikes & gear Included

Outdoor spacesValueParking

Cottage in Clearwater Beach

4.77 out of 5 average rating, 172 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

ValueOutdoor spacesSleep quality

Cottage in Pass-a-Grille Beach

An inviting dining space displays a wooden table paired with white chairs, complementing light blue walls. A small sideboard houses essentials, while natural light streams through a large window. The open layout connects to a cozy living area with a television and tasteful decor.

4.81 out of 5 average rating, 313 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Outdoor spacesLocationAir conditioning

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.

4.69 out of 5 average rating, 169 reviews

Sleep 7 Steps to Beach Pets OK Real Beach Cottage

Outdoor spacesLocationCheck-in

Other holiday rentals with a kayak

4.98 out of 5 average rating, 172 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

LocationOutdoor spacesHospitality

4.89 out of 5 average rating, 36 reviews

Fall special (reduced $+ min stay)-FL Gulf Coast

Outdoor spacesLocationAccess

The image showcases a serene beach scene framed by lush green trees. Soft sand meets gentle waves under a bright blue sky. Vibrant coastal vegetation leads to the sandy shoreline, where silhouettes of beachgoers can be seen in the distance, enjoying the tranquil setting.

4.99 out of 5 average rating, 81 reviews

Oceanfront · Steps to Sand · Free Kayaks

Outdoor spacesLocationAccess

Apartment in Indian Shores

4.8 out of 5 average rating, 10 reviews

Beachfront Island Studio · Walk to Sand #5

Outdoor spacesLocationAmenities

Apartment in Indian Shores

5.0 out of 5 average rating, 50 reviews

Spacious Beach Condo - Mariner's Pointe

LocationOutdoor spacesQuiet

An open-concept living area features a comfortable sofa, a smart TV, and large windows showcasing views of the Intracoastal Waterway. A dining table for four pairs with additional seating, while a ceiling fan enhances airflow throughout the bright and airy space.

4.88 out of 5 average rating, 26 reviews

Intracoastal Views Condo | 3 min walk to beach!

LocationOutdoor spacesBiking

4.96 out of 5 average rating, 75 reviews

Oceanfront Condo with Beach Access

LocationOutdoor spacesLayout