Holiday rentals with a kayak in St. Pete Beach

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, 156 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

Bungalow in Indian Rocks Beach

4.96 out of 5 average rating, 198 reviews

Your private Waterfront Pool home!

See photos for City holiday event dates! Boat parade ! Street parade! Tree lighting! 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

4.97 out of 5 average rating, 150 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.

4.97 out of 5 average rating, 239 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

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

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.

4.94 out of 5 average rating, 135 reviews

Home in Apollo Beach

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Townhouse in Pass-a-Grille Beach

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.

4.89 out of 5 average rating, 239 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.

Home in Indian Rocks Beach

4.96 out of 5 average rating, 126 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.

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.

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.

4.75 out of 5 average rating, 121 reviews

Breathtaking Beachy Houseboat on Clearwater Island

Experience Clearwater Beach in a truly unforgettable way by staying right on the water! This beautifully houseboat offers the perfect blend of comfort, coastal charm, and a one-of-a-kind waterfront stay. Enjoy peaceful mornings on the deck and stunning sunset views. Complimentary kayaks, paddleboards, 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.

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

Popular amenities for St. Pete Beach 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, 149 reviews

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

Home in Indian Rocks Beach

4.96 out of 5 average rating, 24 reviews

Waterfront, heated pool, golf cart, kayaks & SUP

4.91 out of 5 average rating, 141 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.

4.98 out of 5 average rating, 106 reviews

A serene waterfront view captures a canal lined with homes and docks. The still water reflects the soft hues of the sunset, while palm trees and boats add to the tranquil atmosphere.

Home in Bay Crest Park

Canal views, dock, Manatees, pool and more

4.88 out of 5 average rating, 100 reviews

Aerial view of a beach with soft white sand and turquoise waters, showcasing several beachgoers relaxing under the sun. Residential buildings are visible in the background, indicating a serene coastal community. The shoreline curves gently, inviting exploration and enjoyment of the beach.

Home in Indian Shores

Fabulous Beach House 3BR, SPACIOUS, Beach breezes!

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

5 out of 5 average rating, 14 reviews

An aerial view captures the canalfront property, showcasing the large pool and spa surrounded by tropical landscaping. The private dock accommodates a boat, while a beach area is visible with lounge chairs and palm trees enhancing the waterfront setting.

Home in Apollo Beach

*New* Waterfront Retreat: Pool, Spa, Dock & Views

4.94 out of 5 average rating, 235 reviews

The exterior of a two-story home is featured, set in a lush, green environment near a tranquil lagoon. Tall trees and hanging moss frame the structure, which is elevated slightly above the water. The calm water reflects the house and surrounding foliage.

Home in Tarpon Springs

Tree House Treasure

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, 296 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

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, 180 reviews

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

4.91 out of 5 average rating, 128 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

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

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

4.83 out of 5 average rating, 111 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

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

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

Other holiday rentals with a kayak

Townhouse in Treasure Island

A well-maintained pool area overlooks a calm canal, featuring lounge chairs arranged along the pool's edge. Palm trees provide shade, and the clear water reflects the bright sky. Dock space is visible in the distance, suggesting easy access for water activities.

5 out of 5 average rating, 4 reviews

Beautiful Hidden Gem of Treasure Island

5 out of 5 average rating, 51 reviews

Aerial view of the property highlights a private dock with a kayak, surrounded by lush tropical landscaping. A tiki dining hut is situated on the spacious lawn, providing a serene outdoor space. The waterway can be seen flowing alongside the home, enhancing the natural setting.

Home in Largo

Manatee Cove Waterfront • Heated Pool, Dock, Kayak

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!

5 out of 5 average rating, 13 reviews

Condo in Indian Shores

Peaceful Penthouse Escape | Oceanfront View & Pool

Townhouse in Sunset Beach

A well-appointed bedroom features a spacious bed with soft, neutral bedding, complemented by decorative throw pillows. Art pieces depicting beach scenes adorn the wall above the headboard. Large windows allow abundant natural light and showcase stunning ocean views.

4.76 out of 5 average rating, 59 reviews

Beach Haven B4 Secluded Beachfront Striking Views

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

4.9 out of 5 average rating, 10 reviews

A bright living area features light-colored leather sofas and a coffee table, complemented by a ceiling fan overhead. Large sliding glass doors open to a waterway view, allowing natural light to fill the space. A decorative plant adds a touch of greenery to the room.

Condo in Treasure Island

Tides of Capri Treasure Island