Holiday rentals with a kayak in Tampa

4.96 out of 5 average rating, 130 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Outdoor spacesValueAmenities

4.95 out of 5 average rating, 196 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

Outdoor spacesValueDecor

4.97 out of 5 average rating, 174 reviews

The exterior of a waterfront home is shown, featuring a spacious lawn with palm trees and a paved driveway. A screened gazebo is visible nearby, and the calm water reflects the surrounding greenery and sky. The house has a light-colored facade, enhancing its inviting appearance.

Home in Riverview

Beautiful Waterfront Home on the Alafia River.

Beautiful Waterfront Single Family home on the Alafia River leading to Tampa Bay and the Gulf of Mexico. Bring your boats, jetskis, Kayaks, water toys, fishing rods, etc. Riverview Civic Center and Boat Ramp is literally a couple of blocks away from the property and trailer parking is available at the property. If it’s your lucky day, you will see manatees, dolphins, snook, redfish and stingrays right from the dock. Excellent fishing, restaurants and nightlife all on the river or by vehicle.

LocationOutdoor spacesDecor

4.99 out of 5 average rating, 105 reviews

A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.

Guesthouse in Westchase

Cottage in Paradise.

Relax and unwind at our 2 bedroom, 1.5 bath, GUEST HOUSE (ONLY). Enjoy the pool, Beautifully landscaped grounds with Koi pond & mini golf. See birds, butterflies and more in our 1 acre botanical gardens. Free use of Golf Cart. Kayaks are available (with transport fee. I live in the main house and I'm happy to ensure that you have everything you need for an amazing vacation, while still giving you plenty of privacy. Check in & out times are not set & very flexible for your convenience.

LocationOutdoor spacesPool

4.96 out of 5 average rating, 107 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

Outdoor spacesValueTV

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.

4.92 out of 5 average rating, 227 reviews

Luxurious "Riverfront Oasis" - Waterfront w/pool

Luxurious, riverfront home with a coastal-farmhouse design, creating the ultimate Florida getaway or staycation! Spend your vacation relaxing in our private heated, waterfall pool, around the fire pit, or dining on the lit up boat dock. Beautifully furnished and professionally designed with lots of additional amenities, including bathrobes, aromatherapy diffusers, TWO fully stocked kitchens, bluetooth speaker, fishing poles and more! Plus, spectacular views of the Downtown Tampa Skyline!

ValueOutdoor spacesAir conditioning

4.98 out of 5 average rating, 267 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.

LocationOutdoor spacesAccuracy

4.95 out of 5 average rating, 166 reviews

Home in Apollo Beach

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

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

ValueOutdoor spacesIndoor spaces

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, 618 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

LocationOutdoor spacesBeach

4.86 out of 5 average rating, 1023 reviews

A screened-in pool area features a clear turquoise pool bordered by a tile deck. Floating loungers rest on the water's surface. Simple poolside furniture is arranged for relaxation, with lush greenery and scenic views of the Hillsborough River visible through the screens.

Guesthouse in Tampa

Seminole Heights Riverside Paradise w/Pool

Wake up on a quiet bend of the Hillsborough River, where glassy water, towering live oaks, and golden sunsets create a setting that feels both calm and connected. Isla de Dij offers a thoughtfully designed riverfront stay just minutes from downtown Tampa—ideal for work trips, weekend escapes, or anything in between. For those looking to elevate their stay, optional experiences like kayaking, paddleboarding, and sunset cruises are available on the water.

LocationOutdoor spacesView

4.78 out of 5 average rating, 209 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!

LocationOutdoor spacesView

5.0 out of 5 average rating, 169 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

ValueLocationIndoor spaces

Popular amenities for Tampa kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

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.

4.83 out of 5 average rating, 213 reviews

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

Outdoor spacesValueAmenities

4.9 out of 5 average rating, 181 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

Outdoor spacesLocationPool

4.93 out of 5 average rating, 117 reviews

Cheerful Country Home 5 min Amphitheater/Fairgroun

Outdoor spacesLocationView

4.95 out of 5 average rating, 111 reviews

Home in St. Petersburg

Lux Mid-Century Downtown Courtyard+Parking

Outdoor spacesLocationLaundry

4.91 out of 5 average rating, 169 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.

LocationOutdoor spacesIndoor spaces

A welcoming entryway is lined with modern mirrors and a sleek chandelier, guiding guests towards a bright living area. Sunlight fills the spacious room, highlighting a stylish seating arrangement and a dining space with lake views. Outdoors, colorful chairs offer seating by the water.

4.98 out of 5 average rating, 53 reviews

Luxury Water Front Lake house

Outdoor spacesLocationAir conditioning

5.0 out of 5 average rating, 16 reviews

Home in Town 'n' Country

Amazing Experience Imperial Key - Tampa FL

Outdoor spacesLocationCleanliness

4.87 out of 5 average rating, 68 reviews

Home in Town 'n' Country

Luxury Waterfront Oasis With Heated Pool (option)

ValueLocationKitchen

Cottages with a kayak

4.94 out of 5 average rating, 100 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

Cocos Cottage Summer fun! 10% off 6/1-8/31, 2026

Outdoor spacesValueSleep quality

4.97 out of 5 average rating, 144 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

Outdoor spacesValueBeach

4.9 out of 5 average rating, 150 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

ValueLocationWi-Fi

Cottage in Clearwater Beach

4.77 out of 5 average rating, 172 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Outdoor spacesValueCleanliness

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, 313 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Outdoor spacesLocationTV

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

Outdoor spacesLocationParks

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

Elegant Crystal Beach cottage within sea glimpse

LocationIndoor spacesWalkability

Cottage in Tarpon Springs

An aerial view showcases the peninsula of Seabreeze Island, surrounded by tranquil blue waters. The landscape is dotted with homes and docks, with greenery visible in the background. The horizon presents a soft gradient of colors as the sun sets, creating a peaceful atmosphere.

Seaside Cottage- Gulf Waterfront with heated pool

Other holiday rentals with a kayak

4.99 out of 5 average rating, 159 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

Outdoor spacesValueKitchen

4.99 out of 5 average rating, 350 reviews

A spacious cabin is gently illuminated by string lights, creating a warm glow against the evening sky. Surrounding the home are trees and a hammock, with a grassy area leading up to the porch where seating is visible.

Farm stay in Odessa

Farm and lake stay at Maison de L'eau Douce

LocationOutdoor spacesHospitality

4.98 out of 5 average rating, 172 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

LocationOutdoor spacesLong stay

4.99 out of 5 average rating, 163 reviews

An aerial view showcases the property nestled among lush greenery along the Alafia River. A spacious yard is bordered by trees, and a covered pool area is visible. The river reflects the surrounding landscape, contributing to the tranquil setting of the retreat.

Guest suite in Riverview

The Guest House at Riverbend Retreat Fla.

Outdoor spacesLocationCheck-in

4.8 out of 5 average rating, 373 reviews

The exterior of the riverfront suite is portrayed with its charming facade and solar panels. Surrounded by lush greenery, the suite features large windows that provide views of the tranquil river. The inviting porch is visible below, offering a welcoming entrance.

Guest suite in Tampa

Riverfront Suite Jacuzzi tub, Swim Spa & Kayaks

LocationOutdoor spacesWalkability

4.97 out of 5 average rating, 74 reviews

A serene outdoor space features a circular fire pit surrounded by several adirondack chairs. Lush greenery and trees frame the area, while a vibrant sunset paints the sky in soft pastel hues. The lake is visible in the distance, enhancing the peaceful ambiance.

Villa in Thonotosassa

Lakeside Villa

ValueLocationIndoor spaces

4.89 out of 5 average rating, 56 reviews

Home in Town 'n' Country

Waterfront~Firepit~Kayak~HotTub

Outdoor spacesValueFamily