Vacation rentals with a kayak in Largo

Condo in Indian Rocks Beach

A well-maintained outdoor area features a putting green surrounded by lush green turf. Comfortable lounge chairs are positioned nearby, with a table and chairs set against a backdrop of the Intracoastal waterway. A clear blue sky and vibrant foliage contribute to the serene atmosphere.

4.79 out of 5 average rating, 139 reviews

2BR: Intercoastal Views, 3 Min Walk to Beach

LUXURY AWAITS in this 2 BR/1 BA full kitchen condo with unobstructed PANORAMIC WATER VIEWS of the SPARKLING Intracoastal WATERWAY!! Just minutes to the Gulf of Mexico by BOAT or FOOT! Enjoy the SUNRISE off the PRIVATE DOCK or take a 3 minute walk to the beach to ENJOY BREATHTAKING SUNSETS!! The Intracoastal has many advantages including very calm water for: Fishing, Boating, Paddle Boarding, Kayaking, and More! We are also a 3 minute walk to pickleball, basketball, and a fenced in playground!

4.99 out of 5 average rating, 139 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, 117 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

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

4.97 out of 5 average rating, 129 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

2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

4.97 out of 5 average rating, 144 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, 225 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, 139 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, 233 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

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

4.94 out of 5 average rating, 237 reviews

A living area features a plush blue sofa and matching lounge chair, placed on a light blue and white striped rug. Large sliding glass doors open to a balcony, allowing natural light to illuminate the space. A coffee table and a side table complete the inviting setup.

Townhouse in Ruskin

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

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, 124 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.

4.98 out of 5 average rating, 187 reviews

A spacious backyard is highlighted by a hammock suspended between two trees, inviting relaxation. A black dog and a tan dog can be seen exploring the grassy area, surrounded by tall trees adorned with Spanish moss. A guesthouse is visible in the background.

Farm stay in Odessa

Farm and lake stay at Malfini Cay

PRIVATE GUESTHOUSE...Lakefront -full kitchen living room-very large bedroom-full bath-2.5 acres. Newly decorated/remodeled. 2 flat screen TVs-Roku (Netflix and Spectrum app)-WIFI -laminate flooring-high thread count sheets-comfy queen bed. IKEA sleeper sofa in livingroom. All kitchen appliances with coffee bar/Keurig-W/D. Wooded setting-beautiful views of ski lake. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

5 out of 5 average rating, 146 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 Largo kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.95 out of 5 average rating, 40 reviews

A serene backyard oasis is presented, featuring a circular stone patio surrounded by lush tropical plants. A cozy seating area with a fire pit is visible, along with a tall blue umbrella offering shade. The view extends to a calm waterway, bordered by trees.

Home in Ozona

Casa Del Sole

4.91 out of 5 average rating, 136 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

Renovated peaceful 2 Bedroom cottage with/hot tub.

4.98 out of 5 average rating, 100 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 Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

Home in Indian Rocks Beach

5 out of 5 average rating, 8 reviews

Waterfront Manatee Home Pool, Dock, Optional Boat

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, 124 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, 48 reviews

Home in Largo

Quiet Cove w/ Pool+ Dock | Indian Rocks Beach

4.85 out of 5 average rating, 545 reviews

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.

Home in Tampa

Urban River Edge Loft w/Soaking Tub and King Bed

Cottage rentals 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, 290 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, 178 reviews

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

4.91 out of 5 average rating, 124 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

4.84 out of 5 average rating, 106 reviews

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

4.93 out of 5 average rating, 87 reviews

A cozy living space features a dark leather couch and a decorative wooden coffee table. Natural light streams through large windows adorned with blue patterned curtains. A flat-screen TV is mounted on the wall, and a wooden cabinet displays nautical-themed decor.

Cottage in Riverview

Alafia River Cottage

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

Other vacation rentals with a kayak

5 out of 5 average rating, 15 reviews

A spacious living area features a striped, blue and white sofa set with matching armchairs. Large sliding glass doors open to a balcony, providing views of the water. A flat-screen TV is positioned on a low table, and two lamps provide soft lighting.

Condo in Sunset Beach

Land's End 11-404: Gulf Front Gem - 2BD/2BA

Home in Indian Rocks Beach

A heated pool is set within a sunlit patio area, surrounded by tropical palm trees. An outdoor dining set and lounge furniture are positioned near the pool, providing a relaxed space for enjoying the coastal scenery. Bright skies complement the tranquil atmosphere.

4.95 out of 5 average rating, 22 reviews

Wfrt, pool, golf cart, kayaks & SUP BTR 2312

5 out of 5 average rating, 10 reviews

A clear swimming pool rests within a screened enclosure, surrounded by tropical greenery. Comfortable lounge chairs are positioned by the water's edge, inviting relaxation. The pool features a connected hot tub, offering options for leisure and enjoyment.

Villa in Wimauma

Coastal Farmhouse & Pool

Guesthouse in St. Petersburg

A compact kitchen is featured with exposed brick walls and wooden shelves. A white stove and colorful microwave are placed on a dark wooden counter. Various cups and decorations are neatly arranged on the shelves, contributing to a cozy, functional space.

4.85 out of 5 average rating, 33 reviews

Key Rossman

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, 26 reviews

Waterfront Apartment with Dock inTreasure Island

4.89 out of 5 average rating, 9 reviews

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.

Condo in Indian Shores

Charming Intracoastal Condo - 3 min walk to beach!

4.96 out of 5 average rating, 95 reviews

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.

Condo in Indian Shores

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