Vacation rentals with a kayak in Hillsborough County

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Top-rated kayak rentals in Hillsborough County

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Guest favorite

Home in Apollo Beach

4.98 out of 5 average rating, 127 reviews

5 Bed/4 Bath Waterfront "Lay Low" in Apollo Beach

Apollo Beach Waterfront Home with Pool & Hot tub, 4 bedroom-4 private baths & elevator. Theater room-murphy bed (5th bedroom). Game room - pool, air hockey... Enjoy kayaks, paddle boards, fish at the dock or book a boat charter with owner, 20% off for guests. 3 restaurants - walking distance. Apollo Beach - 1/2 mile away! Bahia Beach -2 restaurants and EG Simmons Beach - 20 min away. Bring your boat, dock at house, Apollo Beach Marina - 2 min. away. Animal-free home due to severe allergies.

Superhost

The waterfront property is surrounded by lush greenery and features a multi-level building with palm trees. A boat rests by the dock, while calm waters reflect the serene landscape. The inviting outdoor space includes seating areas, creating a peaceful riverside atmosphere.

Guest suite in Tampa

4.8 out of 5 average rating, 181 reviews

The Borough Riverside Retreat

Located on the Hillsborough River in the heart of Tampa. Stores, parks, restaurants and bars within walking distance. The private suite is smaller in size but warm and cozy, it has a queen bed with luxuries likens Jacuzzi tub, a Kitchenette with a mini fridge, microwave, toaster oven, , HD TV, Ice Cold A.C. and more. The property has a heated swim spa, firepit , swing area w/ hanging bed, hammock, fishing dock, outdoor shower, kayaks, Jon boat, bikes, lawn chairs to catch some rays and more..

Guest favorite

Two kayaks sit on a wooden deck, one orange and one white. The background features a private dock above a serene waterway, with green mangroves providing a natural backdrop.

Home in Clearwater

4.97 out of 5 average rating, 29 reviews

Waterfront Private Dock 4BR/2 Bath kayaks/Hot Tub!

Come relax on the water! Kayak out to Tampa bay or watch the kids kayak while you enjoy the hot tub! Fish from the private dock or sip your coffee from the large deck and covered patio! Your family will be close to everything when you stay at this centrally-located place. Waterfront home only a few minutes from the most beautiful beaches on the Florida West Coast. Located just across from protected mangroves, you’ll feel like the only ones on this beautiful waterway that leads out to the bay.

Guest favorite

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

4.97 out of 5 average rating, 116 reviews

A little piece of Heaven

It is a truly cozy cottage, with all the amenities of home with a lakefront view. There's a firepit outside for those colder nights and kayaks and peddleboats for the more adventurous ones, or just sit back and take in some sun on the new 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 here.

Superhost

Two kayaks are positioned on a grassy area near the water's edge. One kayak is blue and the other yellow, with paddles resting inside. Lush green trees frame the scene, and a dock is visible in the background, leading to calm waters.

Island in Gibsonton

4.8 out of 5 average rating, 5 reviews

Island Retreat Florida

Please read before booking! Ever wonder what it would be like to stay on a deserted island? This is truly an adventure you will never forget. Once you land in paradise you will wander thru the looping trail system to find your campsite. There are (4) campsites with elevated tent platforms tucked in the trees. Settle in and gather wood to build a fire in one of the (2) 8 foot concrete fire pits. There is an outhouse on the property for a more enjoyable stay. We are also working on a shower.

Superhost

An aerial view presents a charming bungalow situated alongside a serene waterfront. Lush greenery surrounds the property, complemented by outdoor seating areas along the edge of the water. The reflection of the trees and sky creates a peaceful atmosphere on the calm surface of the river.

Apartment in Tampa

4.81 out of 5 average rating, 469 reviews

↱Riverfront Escape w/included kayaks near dwntwn↰

Relax by the firepit, paddle the Hillsborough River in the included kayaks or paddleboard, or fish in your own oasis with endless views of birds and wildlife all while being just 5 minutes from world class restaurants all along Florida Ave in Seminole Heights and Zoo Tampa 10 minutes from Ybor City and Downtown Tampa, Riverwalk and Armature Works, and Amalie Arena 13 minutes from the airport and Busch Gardens 45 minutes from Clearwater Beach and 0 minutes to an epic sunset view!

Superhost

Home in Tampa

4.82 out of 5 average rating, 114 reviews

Paradise Pool Home with Canal Access to Tampa Bay!

Waterfront Paradise by Tampa Bay! This centrally-located, newly updated 3-bed, 2-bath haven offers fantastic canal views.  Enjoy your private dock directly on the canal—perfect for docking your jet ski rental. Have a great fishing day, or take our kayaks to see manatees at Manatee Bend just down the canal! Take a dip in the pool for ultimate relaxation. - 10 min to beach - 8 min to airport - 8 min to mall - 25 min to bush gardens - 25 min to the aquarium - 20 min to the zoo

Superhost

A vibrant green lawn leads to the water's edge, accented by a palm tree. Kayaks in bright colors are stacked nearby, with a wooden fence visible in the background. Clear skies and gentle clouds create a serene atmosphere.

Condo in Dunedin

4.85 out of 5 average rating, 26 reviews

Nautical Landings West-Honeymoon Island Pass.

The Starboard Bow is one of 4 suites inside Nautical Landings, our Gulf-front fourplex in Dunedin, Florida. It's on the first floor, and features gorgeous views of the water right outside the patio. Sit on the dock , paddle one of our kayaks to a nearby island, or visit downtown Dunedin for some world-famous carrot cake or a brew at one of the pubs. *There is no trailer parking or boat ramp at Nautical Landings. Please contact us for more information* *90-day reservations*

Guest favorite

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

4.95 out of 5 average rating, 212 reviews

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.

Superhost

Two red kayaks are positioned on yellow wheeled carts, ready for transport. Each kayak is equipped with paddles, secured on the deck, and features blue gear neatly stored inside. The surface beneath is paved, indicating an easy launch area.

Townhouse in Ruskin

4.94 out of 5 average rating, 221 reviews

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.

Guest favorite

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

4.99 out of 5 average rating, 134 reviews

The Guest House at Riverbend Retreat Fla.

True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.

Superhost

Two kayaks, one orange and one beige, are stored beneath a wooden staircase. A rack holds multiple bicycles, hinting at recreational options nearby. The scene is framed by wooden fencing and soft gravel underfoot, creating a relaxed outdoor environment.

Apartment in St. Petersburg

4.81 out of 5 average rating, 129 reviews

Sunshine St. Pete | 400ft² | bikes | kayak|netflix

♡ 400ft² private craftsman studio apartment on shared property ♡ ☞ Walk Score 82 (walk to cafes, dining, shopping..) ☞ Bike Score 75 (2 bikes provided) ☞ Memory foam mattress + sofa couch ☞ Fully equipped + stocked kitchen ☞ Free kayaks + beach gear ☞ Beach gear provided ☞ Onsite parking ☞ Swivel Smart TV w/ Netflix ☞ 214Mbps Wi-Fi ☞ AC & Heat 5 min → Salvador Dall Museum, Vinoy Park, St. Pete Pier 15 min → Airport & St Pete Beach