Vacation rentals with a kayak in Spring Hill

A charming pirate-themed home on stilts sits surrounded by lush greenery. The elevated structure features a porch with seating, providing a view of the tranquil river below, where kayaks can be seen ready for use. The inviting space offers a comfortable atmosphere for relaxation.

4.92 out of 5 average rating, 200 reviews

Weeki Wachee Pirate House - 6703 W. Richard Dr.

Embellish in this once in a lifetime, perfect getaway on Weeki Wachee River. A local favorite! Fully furnished pirate themed, 500 sq ft home with 1 bedroom 1 bath full kitchen and sofa bed. It has everything needed to create unique memories. Swim with manatees in the crystal clear spring-fed river. Have your coffee on the porch over looking the water and your favorite drink around the fire at night. Kayaks are included. Minutes from Weeki Wachee mermaids, Pine Island Beach and Homosassa Springs.

4.87 out of 5 average rating, 101 reviews

Capt Jack's w/SUP, Jacuzzi, Game Rm, kayaks, dock

Escape to our newly remodeled (2025) never been flooded upriver home in Weeki Wachee, FL, just 1 hour N of Tpa boasting professionally cleaned, comfortable accommodations. Enjoy a private Jacuzzi, an expansive game rm with a LG smart TV, 2 SUP, 5 Kayaks, 4 relaxing RiverTubes +, a giant float mat, & yoga mat on one of the best upriver canals just off the main river. The perfect retreat for those seeking relaxation & adventure in nature's paradise. Secure your date with a deposit while it lasts.

An aerial view of a spacious three-story home is presented, bordered by lush greenery and palm trees. A private dock extends into the water, featuring seating areas for relaxation. The surrounding area is tranquil, showcasing a blend of natural and residential scenery.

4.99 out of 5 average rating, 100 reviews

Newly Offered-Great Location - Sleeps 12 + Kayaks

Gulf Access +LOCATION!The whole group will enjoy easy access to everything from this centrally located place. See the drone photos on this ad. This home is ONLY a 5 min via kayaks to : The Main Weeki Wachee River + Rogers Park Playground + Rogers Park Beach + Rogers park Boat Ramp + Jon Boat Rentals + Upper Deck Resturaunt & located on a Deep- Water channel just a couple streets off Shole Line Blvd. Bicycles and Kayaks are included so you can experience the River Life to the fullest!

A charming cottage exterior is surrounded by tropical trees and well-maintained grass. The building features a mix of blue siding and stone accents, while large windows offer natural light. A cozy patio area with lounge chairs invites relaxation.

4.93 out of 5 average rating, 248 reviews

Weeki Wachee, Florida Entire House- 2 bed 2 bath

Come and relax in our newly remodeled river front cottage. This spacious two bedroom two full bath home sits nestled between beautiful tropical trees on the crystal clear river that leads out to the gulf of mexico. The 20 x 20 master suite consist of a king bed, custom two person rain shower and walk out private balcony. First level has an open floor plan with a fully stocked kitchen ready to entertain family and friends. The garage has 6 kayaks, life jackets, fishing gear, washer and dryer.

Two kayaks, one red and one orange, are anchored near a wooden dock by a turquoise building. Four blue Adirondack chairs are positioned on the patio, which overlooks a grassy area and a canal. Large windows allow natural light into the space.

4.93 out of 5 average rating, 179 reviews

Little Bohemia! Waterfront+kayaks+dock+tikitub

It is impossible not to fall in the love with the Weeki Wachee River - it's magical! The Little Bohemia Lodge is the perfect waterfront getaway - a perfect mix of retro and updated - you'll love the funky fun touches! You will probably find yourself spending most of your time out back watching manatees float by, grilling out, or sitting by the fire pit. Our outdoor Tiki Tub is perfect for hot baths after the cool river! The property comes with 2 tandem kayaks and 2 singles for your enjoyment.

4.95 out of 5 average rating, 117 reviews

A cottage featuring a light blue exterior is surrounded by greenery and mature trees. The front yard is spacious, with a gravel pathway leading to the entrance, and the sunset casts warm colors across the sky.

Cottage in Spring Hill

Weeki Wachee cottage getaway

Weeki Wachee cottage that sleeps 4. Bedroom has a king and the couch pulls out and sleeps 2(kids). Plenty of space outside to park your boat, trailer, or toys. There is a 10x20 RV pad with 30A hookup available for extra. No dump station. Two kayaks, fish cleaning table, fire pit, horseshoes, cornhole, netted gazebo, smartTV, propane grill, board games, laundry. 1 dog w/fee. Hammock outside. WW Springs Park- 3 min drive. Rogers Park - 6 mins /Jenkins, & Linda P are 7 mins. Bayport Park 10 min.

Superhost

A serene canal setting is highlighted, featuring calm waters reflecting the surrounding greenery. Boating docks are visible along the banks, with multiple boats moored. Lush trees create a natural backdrop, while the peaceful atmosphere invites relaxation.

4.82 out of 5 average rating, 122 reviews

Flip Flop River Stop

Throw on the flip flops and take it easy at this unique and tranquil getaway! Canal front dock with ladder to enjoy the visiting manatees or a quick paddle to the beautiful, clear Weeki Wachee river In the provided kayaks. Paddle to the springs or enjoy quick boat access to the Gulf for fishing or scalloping. Visit Pine Island, Weeki Wachee mermaids and Buccaneer Bay. One hour north of Tampa. Pets allowed. Must be declared! Max 2 (under 50 pounds each). **Monthly/weekly discounts on booking!

A screened-in outdoor space features a large patio area with several lounge chairs and a dining table, all overlooking the river. A kayak is stored nearby, and a built-in ladder leads down to the water for convenient access.

4.97 out of 5 average rating, 174 reviews

Wasted Time on the Weeki Wachee - Kayak & Manatees

Manatees, fishing, kayaks, crystal clear water and the best location await you at "Wasted Time," our waterfront retreat on the beautiful Weeki Wachee river, minutes from Rogers Park. This 2/2 stilt home is comfortably furnished, sleeps 6 and comes complete with all the essentials and toys you could imagine, including boat dock. It features a large, screened in balcony patio overlooking the river, and an entire screened in entertaining space underneath the home. Direct access to the Gulf!

The waterfront property is shown with a two-story building featuring a covered balcony and large windows. Adirondack chairs are positioned on the lawn, with a wooden dock extending into the water. A boat lift and multiple kayaks are visible nearby.

4.82 out of 5 average rating, 237 reviews

Captain's Quarters at Pirate's Cove

Located just 10 houses from the Weeki Wachee River on a beautiful canal, you will enjoy the sights, the sounds and the perfect mix of relaxation and adventure! Pirate's Cove consists of two units on one property. Mermaid Landing is a 1/1 downstairs with the capacity to sleep 4. Captain's Quarters is upstairs and is a 2/1 with a screened in porch and open balcony. They are completely separate and private but could be opened up for a larger gathering if both were rented together.

A modern kitchen features blue cabinets and stainless steel appliances. Natural light fills the space, highlighting the countertop's clean design. The open layout connects seamlessly to a living area, which includes light-colored furnishings and decorative rugs, creating a welcoming environment.

4.96 out of 5 average rating, 121 reviews

Weeki Wachee River Escape Waterfront Home w/Kayaks

Stay at this Weeki Wachee River Escape! 2 BR, 2 BA, updated coastal-themed home on the river that sleeps up to 6 people with a floating dock! The main house has a large master BR with king bed, full bath, beautiful kitchen and living room with bunk beds (twin and full) The patio is screened-in and has a dining and seating area. The little house has a queen bed, full bath and washer/dryer. Relax out back by a fire pit or cookout on the grill and enjoy the 5 kayaks and paddle board!

A stone pathway leads to a small fire pit, surrounded by two brightly colored chairs. The serene waterfront scene includes a wooden dock and a canal lined with houses and greenery, reflecting a tranquil outdoor space.

4.91 out of 5 average rating, 260 reviews

"Ruf'n It" On The River w/kayaks

"Ruf'n IT" is a 2/1 Waterfront home w/ TV/WiFi just off the main river w/ 7 single kayaks and a youth paddle board. There is dock space for your boat, canoe, or kayaks w/ space to park your trailer. The living space provides 1250 squ ft w/dining area. Enjoy the peace and quiet on the screened lanai and a spiral staircase up to the loft w/TV and kid space. The master bedroom provides a king size bed while the 2nd bedroom has 2 queens and bunks. ASK ABOUT OUR JON BOAT RENTAL!

A river house is depicted, featuring a wide deck with yellow railings. Below, a sandy area is surrounded by stones, with two blue lounge chairs and a sliding board leading into the water. Kayaks and a boat are visible nearby, along with greenery and a clear blue sky.

4.99 out of 5 average rating, 203 reviews

Riverfront Escape on the Weeki Wachee with Kayaks

Relax and enjoy the peaceful beauty of the Weeki Wachee River in this riverfront retreat with kayaks included and boat rentals available. Our 2BR/2BA home sleeps 8 with two queen beds and two futons, perfect for families and friends. Lounge on the deck, sip drinks in the lanai, or launch into crystal-clear springs for kayaking and wildlife watching. Minutes from Weeki Wachee Springs State Park, beaches, dining, and shopping — the ideal mix of adventure and relaxation.

Popular amenities for Spring Hill kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The backyard features a vibrant landscape with lush greenery surrounding the canal. A wooden dock is visible, along with kayaks ready for use. Multiple seating arrangements, including picnic tables and colorful chairs, create inviting outdoor spaces for relaxation and gatherings.

5 out of 5 average rating, 51 reviews

Upriver Waterfront: Kayaks & Movie Theater

Home in Sea Ranch on the Gulf

At night, a cozy firepit is surrounded by lush palm trees, providing a serene atmosphere. Soft lighting highlights the adjacent outdoor space of the home, where comfortable seating is arranged, creating an inviting spot for relaxation by the water.

4.88 out of 5 average rating, 69 reviews

SunWild Ventures Home *Golf Cart & Kayaks*

4.97 out of 5 average rating, 34 reviews

Paddle. Play. Unwind. Waterfront River Escape

The image showcases a modern, multi-level structure set against an evening sky. A well-lit fire pit is centered in the foreground, surrounded by several dark wooden chairs. The large screened patio features outdoor seating, with steps leading to the upper levels of the home.

5 out of 5 average rating, 23 reviews

Dreamy Waterfront Getaway in Weeki Wachee

The exterior of a turquoise cottage is set among lush greenery and palm trees. A serene path leads to the front entrance, featuring steps flanked by white gravel and small shrubs. The inviting porch is adorned with white railings and symmetrical windows, enhancing the home's charm.

4.98 out of 5 average rating, 64 reviews

Charming Flip Flop Cottage - A perfect get away!!

An inviting view of the home from the water showcases a two-story structure surrounded by lush greenery and palm trees. The serene water reflects the sunlight, enhancing the tranquil atmosphere of the natural setting. A porch is visible on the upper level, offering seating.

4.83 out of 5 average rating, 66 reviews

Serenity Creek

4.92 out of 5 average rating, 13 reviews

The Bayport Pearl

Superhost

A wooden dock extends into the calm waterway, featuring a grill and two chairs positioned at the edge. Surrounding structures include boats and homes, contributing to a serene atmosphere typical of a waterfront community.

Home in Sea Ranch on the Gulf

4.73 out of 5 average rating, 44 reviews

Gulf kayaking paradise for relaxing Florida visit!

Cottage rentals with a kayak

4.86 out of 5 average rating, 182 reviews

A collection of four kayaks is displayed on a grassy area beside a canal. The kayaks are in bright colors: yellow, turquoise, and green. Surrounding palm trees and a view of the water create an inviting outdoor setting.

Cottage in Weeki Wachee

Relax Canalside at our Cottage, fast 200mbps wifi

Superhost

Cottage in Clearwater Beach

4.78 out of 5 average rating, 162 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

4.99 out of 5 average rating, 92 reviews

An aerial view captures a lush, green landscape surrounding the canal and river. Clusters of homes are interspersed among trees, with a variety of colorful roofs visible. The winding waterway reflects the surrounding nature, providing a serene backdrop to the area.

Cottage in Homosassa

Live Life Now Canal Cottage: Dock, Kayaks, & Bikes

4.98 out of 5 average rating, 248 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

4.89 out of 5 average rating, 19 reviews

A large, partially covered deck offers a view of the canal, accented by palm trees and a clear blue sky. Outdoor seating areas include a wooden rocking chair and several dining chairs, inviting relaxation by the water's edge.

Cottage in Hudson

Water Front Nautical Haven

4.92 out of 5 average rating, 369 reviews

Two kayaks glide through calm waters, surrounded by lush greenery and residential properties along the canal. Brightly colored kayaks in orange and yellow contrast against the serene blue water. Sunny trees provide shade and reflections are visible on the water's surface.

Cottage in Weeki Wachee

Kayak Kottage: waterfront, kayaks, bikes, dockage

4.95 out of 5 average rating, 223 reviews

A cozy bedroom features a metal bed with a soft white spread and decorative teal accents. Natural light enters through two windows framed by light blue curtains. A matching blue cabinet and bedside tables with lamps add functionality and warmth to the space.

Cottage in Weeki Wachee

Coastal Cottage Getaway

4.89 out of 5 average rating, 175 reviews

The cottage is situated on a peaceful corner lot by the canal, offering views of its blue exterior and a welcoming porch. Lush greenery surrounds the property, and a clear blue sky reflects in the calm water, enhancing the serene atmosphere.

Cottage in Spring Hill

Weeki Wachee Barefoot Cottage, Waterfront, Kayak’s

Cabin rentals with a kayak

5 out of 5 average rating, 28 reviews

A private wooden dock extends over calm waters, surrounded by lush greenery and trees. The reflection of the natural surroundings is visible in the water, creating a tranquil ambiance. A palm leaf adds a touch of tropical element in the foreground.

Cabin in Homosassa

Chaz River Charmer

4.97 out of 5 average rating, 161 reviews

The cabin is surrounded by lush greenery, positioned on a private peninsula. A spacious deck with seating faces the water, offering a serene view of the canal. Natural light filters through the trees, illuminating the inviting structure.

Cabin in Floral City

Private Waterfront Cabin Retreat with Kayaking

Cabin in Lake Panasoffkee

A cabin with a rustic exterior features a front porch with a swing. Picnic tables are arranged on a patio area, surrounded by grassy spaces. Lush greenery is visible in the background, providing a serene outdoor setting.

4.89 out of 5 average rating, 157 reviews

Lake Pan Cabin #1

5 out of 5 average rating, 108 reviews

A wooden walkway leads down to the water's edge, flanked by two sets of Adirondack chairs. Lush green trees provide shade along the banks of the calm river, enhancing the peaceful riverside setting.

Cabin in Spring Hill

A Frame Stream Dream-WeekiWachee River

4.96 out of 5 average rating, 76 reviews

The exterior of a tiny cabin features a wooden deck with two red chairs and a welcoming sign. The cabin is painted in warm orange with contrasting gray trim, and multiple windows allow natural light. A wooden fence surrounds the yard, providing privacy.

Cabin in Land O' Lakes

Tiny Lakefront Cabin

4.86 out of 5 average rating, 184 reviews

A tranquil log cabin is nestled among lush greenery, with a wooden deck extending over calm waters. The surrounding trees provide shade, while the cabin's rustic exterior blends harmoniously with the natural environment, creating a serene retreat.

Cabin in Nobleton

Log cabin on the river