Holiday rentals with a kayak in Hernando Beach

A boat deck is presented with a shaded area featuring a built-in grill and multiple seating arrangements. Lush green grass leads from a paved pathway to the water's edge, while palm trees and tranquil waters create a serene setting.

4.99 out of 5 average rating, 131 reviews

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!!

4.91 out of 5 average rating, 184 reviews

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.

Home in Spring Hill

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.

4.93 out of 5 average rating, 241 reviews

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.

Home in Spring Hill

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.

Home in Sea Ranch on the Gulf

The exterior of a freshly redone home is visible, featuring a combination of yellow siding and stone accents. A welcoming sign is positioned near the entrance, surrounded by colorful flower beds with various blooms and maintained landscaping, creating an inviting approach to the property.

4.86 out of 5 average rating, 118 reviews

Waterfront house near Gulf of Mexico

Freshly redone home that is yours to enjoy. 2 bedrooms and 2 bathrooms that can accommodate 4 guests. Enjoy the gorgeous sunsets from either the screened-in back porch or the dock on the canal. Or, jump into the kayak and paddle a very short distance (7 houses down the canal) to the Gulf of Mexico. Fishing tackle and poles are available. Friendly, quiet neighborhood that is great for walking or riding the bikes that are included with the house. Plenty of restaurants or shopping nearby.

An aerial view showcases the property with a spacious pool integrated into the backyard. A well-maintained dock extends into the water, illuminated by a green light, accompanied by colorful kayaks. Nearby, palm trees add greenery to the inviting outdoor space.

4.91 out of 5 average rating, 109 reviews

Waterfront home heated pool+jacuzzi+game room+golf

Bring your boat or rent nearby! Minutes to prime SCALLOPING waters. Enjoy a HEATED pool, jacuzzi, putting green, ping pong table, massage chair, arcade basketball, paddle boards, kayaks, bicycles, four jetski docks & boat dock. FISH CLEANING STATION ON DOCK. Open floor plan with 3 BR, 3 BA and comfortably sleeps 16. Near boat ramp w/ access to Weeki Wachee springs. Great home for sunset cruises, scallops, dolphin &manatee watching, minutes to bike and hiking trails! Pet friendly!

Superhost

The exterior view of Seascape is captured, displaying a multi-level home by the water. Two boat docks are seen along the shoreline, with lush landscaping nearby. A screened patio is visible on the middle floor, while expansive water views stretch across the image.

4.8 out of 5 average rating, 172 reviews

Seascape - WHOLE HOUSE 360 water views, pool, gulf

Enjoy the ENTIRE property at Seascape, a spectacular home with expansive water views, heated pool, and instant access to the Gulf. 4BRs, 3 baths + living + family + dining + 2 kitchens + heated salt-water pool + gym + 3 screened patios + 2 boat docks + large deck by water + Laundry room. Escape to kayaking, scalloping, fishing, pool and Florida sunshine all at Seascape! 5 mins drive to Weeki Wachee, 1 hr to Tampa, 2 hrs to Disney, minutes to restaurants, boat rentals, super Walmart...

4.97 out of 5 average rating, 238 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.

Two individuals are seen fishing from a large private dock next to calm waters, with a boat anchored nearby. Spacious Adirondack chairs offer comfortable seating, while houses with porches and greenery can be observed across the canal under a clear sky.

4.95 out of 5 average rating, 191 reviews

Waterfront | Gulf access | 4 Kayaks | Weeki Wachee

Single level. Waterfront, direct Gulf access, large private dock for fishing and boats! Bring your boat or rent one nearby at the Marina, just a few minutes away! Features: - 4 kayaks - EV Charging. - toiletries, cleaning supplies, ziplock bags, aluminum foil, etc all included - fully loaded kitchen - spices, lots of appliances, Calphalon pots and pans, lots of utensils, etc... - complimentary coffee bar (ground coffee, French Press, kcups, creamers, sugars - see pix for more info)

4.96 out of 5 average rating, 113 reviews

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.

Home in Spring Hill

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!

5 out of 5 average rating, 122 reviews

The kitchen features light turquoise walls and dark wood cabinetry. Open shelving displays dishware and decorative items. A stainless steel stove and microwave are installed, with a large sink beneath a window. Counter space is available for meal preparation and dining.

Home in Sea Pines

Rachel's Place

Hudson is the best kept secret in Florida. This 2/2 is located just 200 yards from the Gulf of Mexico in the beautiful Sea Pines development. This home is nestled next to thousands of acres of wildlife bird sanctuary. There are kayak trails to follow for hours. Redfish, Sea trout and Mangrove snapper are abundant. This beautifully decorated home is well stocked with anything you may need. There are 2 Kayaks, one two person and one single, 2 adult bikes, and fishing equipment.

4.99 out of 5 average rating, 163 reviews

A colorful cottage with a screened lanai rests along a serene river. Kayaks and a floating island are docked nearby, with reflections shimmering on the water. Lush greenery surrounds the property, creating a tranquil outdoor setting ideal for relaxation and recreation.

Cottage in Spring Hill

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

Guest suite in Weeki Wachee

A blue kayak rests on a wooden dock surrounded by vibrant pink flowers. Still waters reflect the colorful homes in the background under a partly cloudy sky, creating a serene and inviting space for outdoor activities.

4.98 out of 5 average rating, 270 reviews

Harbormaster’s Loft-Nature and Kayak

Find your zen...Relax in the surroundings of an 150 acre bird sanctuary. Hear the sounds of the birds and star gaze into the night. Paddle to the crystal clear waters of the weeki wachee from bay lake pond, then 15-20 min nature paddle down canal to river . Observe manatees, birds, otters and turtles , or spend the afternoon at the beach watching dolphins or cast a fishing line into the pond or river..

Popular amenities for Hernando Beach kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

5 out of 5 average rating, 46 reviews

A spacious heated pool area is surrounded by a screened enclosure, featuring clear blue water under bright sunlight. A view of the waterfront is visible beyond the pool, with palm trees and homes reflected in the water. Potted plants add a touch of greenery.

Home in Hudson

Beautiful sunsets, waterfront 2/2 pool home

Superhost

The image captures a serene waterfront scene at sunset, with vibrant pink and orange hues reflecting off the water. A tranquil pool is framed by stone pavers, with palm trees visible in the foreground, creating a calm atmosphere for relaxation.

4.8 out of 5 average rating, 5 reviews

Salt water paradise with a pool

An exterior view of the home highlights a white facade with dark shutters. A well-maintained lawn extends in front, complemented by a few decorative plants. The surroundings are open, with a clear blue sky and scattered clouds.

5 out of 5 average rating, 10 reviews

Home on the canal off the Gulf.

An expansive pool area is featured, surrounded by a lush lawn. The clear blue water is complemented by lounge chairs and an umbrella for shade. A nearby dock can be seen providing access to the waterway, with views of surrounding greenery and homes.

5 out of 5 average rating, 20 reviews

Boater's Paradise. No Hurricane Damage

A two-story house is seen from across the water, featuring a spacious balcony and an attractive roofline. A private dock is positioned in front, with a clean, open area suitable for mooring a boat. Palm trees and lush greenery enhance the waterfront view.

4.98 out of 5 average rating, 88 reviews

Beautiful Home with direct access to the gulf!

5 out of 5 average rating, 36 reviews

Home in Hudson

Waterfront, Gulf Access, Coastal Home

The exterior of a vibrant yellow home features a stone accent wall and a prominent star detail. Lush green grass surrounds the property, complemented by tropical palm trees. The driveway leads to a garage, and an American flag decorates the front, contributing to a welcoming presence.

5 out of 5 average rating, 24 reviews

3 BR Waterfront w/ heated Pool, kayaks and bikes!

4.88 out of 5 average rating, 85 reviews

Home in Hudson

Ryan’s Boat House W/Pontoon boat Gulf Access

Cottages with a kayak

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.

4.86 out of 5 average rating, 181 reviews

Relax Canalside at our Cottage, fast 200mbps wifi

4.99 out of 5 average rating, 83 reviews

Shelter from the Storm | Weeki Riverfront Escape

4.99 out of 5 average rating, 142 reviews

A wooden dock extends into a serene canal, flanked by lush palm trees and vibrant greenery. A gazebo and outdoor seating area are visible in the background, providing inviting spaces for relaxation amidst the tranquil surroundings.

Cottage in Spring Hill

PARADISE POINT on Weeki Wachee (Boat Welcome)

4.83 out of 5 average rating, 111 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

A spacious outdoor deck features various seating options, including woven chairs and bright lounge chairs. A boathouse is visible along the water, surrounded by lush greenery and sunlight filtering through the trees, creating a serene waterfront atmosphere.

4.85 out of 5 average rating, 147 reviews

Welcome to the Weeki Wachee River Boathouse

4.88 out of 5 average rating, 17 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

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.

4.92 out of 5 average rating, 363 reviews

Kayak Kottage: waterfront, kayaks, bikes, dockage

4.89 out of 5 average rating, 170 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

4.85 out of 5 average rating, 177 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 Brooksville

Log cabin on the river

4.92 out of 5 average rating, 13 reviews

The exterior of the cabin is illuminated by string lights, creating a welcoming ambiance. A patio area features seating and a table, while a grill is positioned nearby. A nearby flag adds a touch of character, and greenery can be seen around the space.

Cabin in Port Richey

Cotee River Guest Cabin

5 out of 5 average rating, 99 reviews

A covered outdoor seating area features four dark blue Adirondack chairs arranged around a small fire pit. Wooden decking provides a warm contrast underfoot, while lush greenery lines the waterway in the background, enhancing the serene riverside setting.

Cabin in Spring Hill

A Frame Stream Dream Cedar Cabin-WeekiWachee River

4.88 out of 5 average rating, 32 reviews

A spacious deck is shown with wooden flooring, surrounded by tall trees draped in Spanish moss. A serene lake is visible in the background, reflecting sunlight through the foliage. The scene provides a tranquil setting for outdoor relaxation near the water's edge.

Cabin in Odessa

LakeHouse Cabin Getaway