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.

4.91 out of 5 average rating, 128 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.

4.98 out of 5 average rating, 173 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, 162 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.

Guest suite in Orange Lake Village

A plunge pool features a vibrant blue tiled interior, flanked by a wooden frame. Two pink flamingo floaties rest on the water's surface. A greenery wall in the background is adorned with a softly illuminated sign reading 'Tiny Oasis.'

5 out of 5 average rating, 101 reviews

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, 255 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, 159 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.

4.99 out of 5 average rating, 579 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, 129 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.

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.

4.96 out of 5 average rating, 211 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

5 out of 5 average rating, 100 reviews

Waterfront Duplex: 3 Blocks to Beach, Hot Tub, SUP

☀ Bay Views ☀ 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

4.77 out of 5 average rating, 305 reviews

The living area features a light blue color scheme with a comfortable sofa and armchairs arranged around a glass coffee table. A wall-mounted TV is positioned above a white entertainment unit, and natural light filters through sheer curtains on the window.

Home in Old Southeast

Bungalow 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.

Home in Old Seminole Heights

A well-appointed bathroom features a freestanding soaking tub surrounded by natural stone walls. A double vanity with modern fixtures is situated near the window, allowing for natural light. A glass-enclosed shower and stylish fixtures enhance the functional layout.

4.86 out of 5 average rating, 582 reviews

Urban River Edge Loft w/Soaking Tub and King Bed

A spacious apartment with soaring ceilings encompassing all of the upper story of a historic bungalow, just steps from the Hillsborough River. You'll have your own deck overlooking the river, and be only 10 to 15 minutes from dwntwn Tampa, Amalie Arena, Armature Works, Ray James Stadium, Busch Gardens, & Cypress Point Beach -Complimentary Kayaks Included -Fast WiFi & Smart TV -Soaking Tub -Full Kitchen -Wood Burning Firepit

Popular amenities for kayak rentals in St. Petersburg

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.9 out of 5 average rating, 42 reviews

A spacious front porch features comfortable wooden seating with a table at its center, inviting relaxation. Two ceiling fans can be seen above, and green plants hang from the eaves. Natural light filters through the open space, highlighting the porch's wood ceiling.

Home in Uptown

3-bedroom + Loft Historic Craftsman Bungalow

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

4.91 out of 5 average rating, 152 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, 92 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!

4.88 out of 5 average rating, 105 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, Bikes-Kayaks-SUP

4.9 out of 5 average rating, 10 reviews

Home in Redington Shores

Billy's Beach Bungalow

5 out of 5 average rating, 29 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

Waterfront Manatees with Flamingo Flair, Paradise!

4.92 out of 5 average rating, 212 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

Cottage rentals with a kayak

Cottage in St. Pete 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, 303 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Clearwater Beach

4.77 out of 5 average rating, 164 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Cottage in St. Pete Beach

4.89 out of 5 average rating, 184 reviews

Steps2Beach-Walk everywhere-Bikes & gear Included

4.9 out of 5 average rating, 143 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, 165 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

4.78 out of 5 average rating, 131 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

4.89 out of 5 average rating, 37 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

Other holiday rentals with a kayak

4.98 out of 5 average rating, 47 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 Treasure Island

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.

4.94 out of 5 average rating, 17 reviews

Sunrise & Sunset Water Front Condo

Guest house in St. Petersburg

An outdoor view of the cottage features a window with decorative lights and a vibrant blue door. Two black patio chairs are positioned outside, facing the window, creating a cozy atmosphere for relaxation.

5 out of 5 average rating, 10 reviews

JLs Pineapple Cottage - 2 blocks 2 Bay, 4 to City!

5 out of 5 average rating, 5 reviews

Waterfront • Walk to Beach • Pool • Kayaks • Bikes

4.9 out of 5 average rating, 10 reviews

Flat in St. Petersburg

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

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.

Flat in St. Petersburg

Waterside Vacation Rentals Epic View

4.92 out of 5 average rating, 25 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat