Vacation rentals with a kayak in Largo

4.93 out of 5 average rating, 152 reviews

A screened-in patio features a heated swimming pool, surrounded by white decking. The pool offers a view of the canal with palm trees and neighboring properties beyond. The tranquil outdoor space is complemented by a backyard with swings and a dock visible in the background.

Home in Town 'n' Country

Waterfront Resort with HEATED POOL!

🌴 Escape to this luxurious waterfront retreat in the peaceful community of Tampa Shores ☀️ an outdoor lover’s dream with direct bay access to the Intracoastal. Enjoy fishing, dolphin 🐬and manatee 🌿🦭 watching, or simply relax on your private dock surrounded by nature. Start your morning with coffee ☕️ on the second-story screened patio, offering breathtaking canal views and overlooking the heated private swimming 🏊‍♀️ pool below. The possibilities are endless! Lay back and enjoy your stay!

4.96 out of 5 average rating, 205 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

4.83 out of 5 average rating, 136 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

Enjoy best of Florida in this Updated and Newly Furnished 4 bed, 3 bath with PRIVATE SCREENED HEATED SALT WATER POOL and HOT TUB + FLORIDA ROOM+ GAME ROOM located short 3 miles to the beach. This home is in the quiet neighborhood, close to shopping, restaurants, grocery shops and beach. House accommodates up to 10 guests and has 1 KING BED and 3 QUEEN BEDS and 1 Bunk Bed for sleeping arrangements Both Living room and Florida room have Large Sectional Sofas Grill is available in the backyard

4.97 out of 5 average rating, 174 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.

4.91 out of 5 average rating, 191 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 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.

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...

4.95 out of 5 average rating, 232 reviews

A spacious living area features a large sectional sofa, complemented by decorative tables and potted plants. Expansive windows provide views of the water and outdoor seating, while natural light brightens the modern, open layout.

5.0 out of 5 average rating, 100 reviews

Walk to Beach! Waterfront Lux Retreat w/Kayaks

As seen on the Emmy award-winning show, Staycation. Experience the serene beauty of a waterfront Indian Rocks Beach Home. Wake up to breathtaking views of the water, right from your window. Enjoy the luxury of kayaking or fishing off your private boat dock. Spend evenings gathered around the fire pit or showcase your culinary skills with our grill. Just a 7-minute walk and you'll find yourself on the pristine white sands of Indian Rocks Beach. Kayaks and boat lift available.

4.97 out of 5 average rating, 145 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.

4.96 out of 5 average rating, 135 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|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches.

4.93 out of 5 average rating, 102 reviews

Salty Air Retreat - Hot Tub | Walk to the Beach!

🌊 Salty Air Retreat | Walk to Indian Rocks Beach | Hot Tub + Kayak & Paddle Board ~ Managed by Sandy Feet Vacation Rentals Welcome to Salty Air Retreat, a spacious and family-friendly Indian Rocks Beach vacation home just a short walk from the Gulf Coast’s beautiful white sand beaches! Enjoy the best of Florida beach living with a private backyard, hot tub, beach gear, kayak, paddle board, and a location close to restaurants, parks, and attractions.

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.

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

4.97 out of 5 average rating, 234 reviews

4.76 out of 5 average rating, 218 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!

Popular amenities for Largo kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.98 out of 5 average rating, 137 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 Town 'n' Country

Canal-front Sanctuary | Manatees, Pool, Hot Tub

4.9 out of 5 average rating, 176 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.

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.

5.0 out of 5 average rating, 200 reviews

Piece of paradise in Indian Rocks Beach.

4.83 out of 5 average rating, 217 reviews

An outdoor area is showcased with a multicolored basketball court in the foreground, leading to a spacious yard. A dining set with an umbrella sits under a tree, and a swim spa is visible in the background, surrounded by manicured landscaping and stepping stones.

Home in Tampa

River Oasis w/ Swim Spa & Hoop Court walk to Zoo

4.93 out of 5 average rating, 15 reviews

Home in Seminole

NEW! Serenity-4BD|2BA Pool Minutes to beach!

5.0 out of 5 average rating, 12 reviews

Home in Largo

Honeysuckle Waterfront | Heated Pool & Near Beach

5.0 out of 5 average rating, 71 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

Magical Manatee Waterfront Cove | Near IRB

4.97 out of 5 average rating, 73 reviews

Home in Largo

SLEEP 18, Heated Pool, Tiki, 5 min to Beach, Kayak

Cottage rentals with a kayak

4.98 out of 5 average rating, 271 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, Private Dock, Romantic, Fishing

4.97 out of 5 average rating, 145 reviews

A serene lakefront view is framed by tall trees draped with Spanish moss. A wooden dock extends into the calm water, providing a space for relaxation. Soft shadows are cast across the lush green lawn, inviting guests to enjoy the peaceful surroundings.

Cottage in Lutz

A little piece of Heaven

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

4.89 out of 5 average rating, 193 reviews

4.9 out of 5 average rating, 152 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

4.9 out of 5 average rating, 40 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

Coastal cottage within sea glimpse

4.96 out of 5 average rating, 73 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

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

4.67 out of 5 average rating, 159 reviews

Cottage in Ruskin

1839 2 Bedroom

Other vacation rentals with a kayak

4.99 out of 5 average rating, 160 reviews

The exterior of a newly constructed barn loft apartment is shown, featuring a wraparound deck accessed by wooden stairs. Beneath the deck, picnic tables and seating areas are visible among the surrounding greenery and trees. The property is set in a spacious outdoor environment.

Barn in Odessa

Cypress Lakes Barn Retreat

4.86 out of 5 average rating, 335 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

5.0 out of 5 average rating, 102 reviews

Guesthouse in Clearwater

Charming Casita Near Two Downtowns & Beaches

Apartment in Clearwater Beach

Waterfront Escape | Steps to Clearwater Beach

4.85 out of 5 average rating, 159 reviews

4.95 out of 5 average rating, 60 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

5.0 out of 5 average rating, 28 reviews

Home in Redington Beach

Ocean Breeze at Redington Beach

4.89 out of 5 average rating, 37 reviews

Condo in Indian Shores

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

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.