Holiday rentals with a kayak in St. Petersburg

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, 130 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.

4.95 out of 5 average rating, 185 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

4.98 out of 5 average rating, 167 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.

5 out of 5 average rating, 121 reviews

Guest suite in Largo

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks

Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

4.98 out of 5 average rating, 260 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.

4.89 out of 5 average rating, 168 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.

Tiny home in Ybor City Historic District

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

4.98 out of 5 average rating, 600 reviews

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

4.96 out of 5 average rating, 133 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.

Cottage in Pass-a-Grille Beach

4.89 out of 5 average rating, 188 reviews

Steps2Beach-Walk everywhere-Bikes & gear Included

Welcome to Paradise by the Sea 🌴 Your comfortable Florida beach cottage just steps from the sand in the heart of Pass-a-Grille. This charming island home offers the relaxed, old-Florida vibe guests love — with the convenience of being able to walk everywhere and rarely move the car. The beach is a quick, easy walk, and restaurants, coffee shops, ice cream, and the local market are all nearby. Guests often say it feels like settling into their home by the beach.

Apartment in Indian Rocks Beach

5 out of 5 average rating, 110 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

4.76 out of 5 average rating, 210 reviews

The kitchen features rich wood cabinetry and gray tile backsplash. Essential appliances include a stove, microwave, and dishwasher. Counter space is enhanced by a wooden cutting board. Open shelving displays glassware, while a drawer reveals kitchen utensils. Ample natural light enters through a nearby window.

Home in St. Petersburg

Cottage near the sea

Welcome to our bungalow by the sea It is just 3 blocks away from waterfront Lassing Park, which can be enjoyed with kayaks and bicycles that are available for free, and perfect for exploring nearby downtown Saint Petersburg and the pier. The house is completely furnished with everything you need for a great stay. Charcoal grill, TV, coffee, Ironing board and iron , Wi-Fi Internet and Beach toys So kick back and relax and enjoy your stay.

5 out of 5 average rating, 163 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. Petersburg kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

A spacious waterfront home is showcased with a pool and lounging area. The outdoor space features comfortable seating arrangements and a patio alongside the water. The second level balcony overlooks the backyard, enhancing the setting with a relaxed vibe.

5 out of 5 average rating, 8 reviews

Amazing Waterfront Home 2BLKS 2 Beach & Restraunts

4.89 out of 5 average rating, 159 reviews

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

4.91 out of 5 average rating, 159 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.

4.95 out of 5 average rating, 95 reviews

A serene view of Tampa Bay is showcased, featuring calm waters reflecting a soft sky. Two private docks, one at an angle, provide access to the water, framed by distant greenery along the horizon.

Home in Ruskin

Silverking Keys Retreat!

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

4.99 out of 5 average rating, 193 reviews

Piece of paradise in Indian Rocks Beach.

5 out of 5 average rating, 30 reviews

A vibrant mural of a flamingo is depicted on a brick wall, showcasing bright colors like pink, yellow, and blue. The surrounding landscaping includes lush greenery and palm trees, framed by a pathway made of pavers that leads toward the mural.

Home in Madeira Beach

The Flamingo Waterfront Bungalow

4.78 out of 5 average rating, 23 reviews

Ocean Blue Villa, Beachfront with Private Pool

4.92 out of 5 average rating, 219 reviews

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.

Home in Tampa

Luxurious "Riverfront Oasis" - Waterfront w/pool

Cottages with a kayak

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, 309 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Clearwater Beach

4.77 out of 5 average rating, 168 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

4.9 out of 5 average rating, 146 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.

4.68 out of 5 average rating, 167 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

4.73 out of 5 average rating, 137 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

4.9 out of 5 average rating, 39 reviews

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

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

4.96 out of 5 average rating, 71 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

Other holiday rentals with a kayak

4.9 out of 5 average rating, 20 reviews

An open-concept living space is illuminated by natural light, featuring a modern kitchen with stainless steel appliances and a granite island. A spiral staircase is prominently displayed, leading to the upper floor, while wooden accents and decorative elements contribute to the welcoming environment.

Condo in Treasure Island

Sunrise & Sunset Water Front Condo

4.96 out of 5 average rating, 52 reviews

An outdoor patio area features a private pool surrounded by a spacious deck. A seating arrangement with chairs and a table is positioned nearby, along with a sauna. The setting is complemented by lush green grass and a colorful sunset sky.

Villa in Seminole

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

Apartment in Indian Shores

5 out of 5 average rating, 4 reviews

Gulf-to-Bay Island Apt · Steps to Beach #1

Apartment in St. Petersburg

4.93 out of 5 average rating, 14 reviews

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

Townhouse in Indian Rocks Beach

5 out of 5 average rating, 22 reviews

Walk2Beach, Heated Salt Pool, Pool Table, GameRoom

4.82 out of 5 average rating, 11 reviews

A serene view of Tampa Bay is captured, displaying calm waters reflecting the colors of the sunset. The horizon features a blend of soft blues and warm tones, while a shoreline with pebbles is visible in the foreground, bordered by gentle greenery.

Apartment in Coquina Key

Waterside Vacation Rentals Epic View

Townhouse in Treasure Island

A clear pool is framed by a spacious deck, with lounge chairs positioned nearby. Palm trees line the water's edge, enhancing the coastal view. A wooden dock extends into the canal, featuring a boat. Colorful townhouses are visible in the background against a sunny sky.

4.94 out of 5 average rating, 16 reviews

A Island of Capri Townhome Sunrise Canal/pool side