Vacation rentals with a kayak in Hernando County

4.99 out of 5 average rating, 136 reviews

Home in Hernando Beach

Firepit, Golf Cart, Kayaks, Pedal Boat, Fishing!

Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard. Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River — perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!!

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, 103 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, 254 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.

An outdoor seating area is featured, showcasing a cozy fire pit surrounded by comfortable sofas. Nearby, several lounge chairs face a calm canal, framed by lush trees and a vibrant sunset sky. The serene atmosphere invites relaxation and enjoyment of the natural surroundings.

4.95 out of 5 average rating, 111 reviews

The River Retreat

Escape to our fully renovated home with a rustic farmhouse style decor that is light and cozy. It is situated on a double lot in a quiet canal on the Weeki Wachee River. Home features a separate studio suite with a king size bed with its own Kitchenette, living room with full size sofa sleeper, 50 inch TV and full bathroom. Upstairs are 2 additional bedrooms and bathrooms. The kitchen upstairs is fully equipped including coffee maker & toaster. This home is an Ideal space for large families!

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.

4.83 out of 5 average rating, 126 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!

4.98 out of 5 average rating, 172 reviews

Lucky Duck Lodge : Enjoy Clear Main River Waters

The BEST location on the MAIN river! INCLUDES 2 single kayaks, double kayak, 2 paddle boards, & canoe. The perfect mix of relaxation and adventure await you at this Weeki Wachee River Spring 2 level house, directly on the crystal clear water MAIN RIVER (not on a canal). Upper level has 2 beds, 2 baths, lower level is a full in-law suite with 1 bed, 1 bath, both have open concept living rooms and kitchens with panoramic view of the river from screened in porches. NO SMOKING. NO PETS.

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, 244 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.

4.95 out of 5 average rating, 127 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, 266 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, 208 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.