Vacation rentals with a kayak in Hudson

4.99 out of 5 average rating, 136 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!!

A serene canal view is captured, framed by lush greenery and trees. The still water reflects the surrounding foliage and sky, creating a natural and peaceful scene. This area offers a glimpse of the tranquil environment perfect for relaxation and outdoor activities.

4.9 out of 5 average rating, 102 reviews

4BR Private Dock, Warm Spring Canal, Kayaks, Canoe

Remodeled Florida home on a warm spring canal with dock and quick access to Gulf of America. Designed by the builder for your weekend retreat, "Camp Therapy" is situated on 2 lots with 100ft of waterfront. Home features hardwood floors, a gourmet kitchen with stainless appliances, custom cabinetry and granite counters. Three balcony views to enjoy abundant wildlife such as dolphins, manatees and marine life. Home has 3 adult kayaks, 2 youth kayaks, 2 stand up paddleboards and 2 canoes for use.

4.99 out of 5 average rating, 102 reviews

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.

Home in Spring Hill

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!

4.93 out of 5 average rating, 250 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, 122 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.

A view of the private dock features wooden posts and a boat lift, with calm water reflecting the surrounding waterfront homes. The scene captures a mix of greenery and colorful buildings in the background, under a cloudy sky that hints at a serene atmosphere.

4.83 out of 5 average rating, 109 reviews

Hudson Beach waterfront house, boat lift, Tiki Hut

**NO CLEANING or PET FEES** Visit is limited to registered guests. List price is for 1 guest: $25/ea additional guest per day (regardless of overnight) with a 6 person limit. Enjoy beautiful canals & manatees/dolphins from the spacious tiki hut. Put your boat on our lift or rent from marina down the street; launch one or all of our 3 kayaks or bring yours; fish from the dock. Walk to: 3 seafood restaurants with live music, Hudson Beach, Robert J. Strickland Park, Skeleton Key Marina

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.

4.81 out of 5 average rating, 173 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...

4.98 out of 5 average rating, 250 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, 199 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)

5 out of 5 average rating, 126 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.

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.

4.99 out of 5 average rating, 176 reviews

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.

4.96 out of 5 average rating, 118 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 beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Popular amenities for Hudson kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Sea Ranch on the Gulf

A bright living area is displayed, featuring a light-colored sofa with pink throw pillows, a round glass coffee table, and two blue accent chairs. A large wall-mounted television shows a scenic landscape, while bar stools line the kitchen counter in the background.

4.98 out of 5 average rating, 46 reviews

Florida Keys escape in Hudson Beach

5 out of 5 average rating, 19 reviews

Waterfront & Gulfview Retreat | Hernando Beach

4.96 out of 5 average rating, 50 reviews

An inviting pool lanai is showcased, featuring comfortable lounge chairs and small tables. An umbrella provides shade, enhancing relaxation by the heated pool. A serene lake view is visible beyond the screened enclosure, surrounded by greenery and residential properties.

Home in Port Richey

Lakefront House with Heated Pool

A serene waterway is depicted, with calm waters reflecting hues of purple and blue in the sky. A wooden dock extends into the water, accompanied by wooden posts. Lush greenery lines the shore, and a few boats are visible at nearby docks.

4.93 out of 5 average rating, 45 reviews

Three Bedroom Hudson Waterfront Getaway w/ Dock!

A hot tub is situated under a gazebo, surrounded by flowing water and lush grass. The view reveals boats docked in the canal, with residential homes visible in the background. Soft lighting strings hang from the gazebo, adding to the serene outdoor setting.

4.91 out of 5 average rating, 43 reviews

Hudson Beach Getaway W/Dock

5 out of 5 average rating, 20 reviews

Private dock | kayaks | basketball | airhockey

Home in Sea Ranch on the Gulf

The outdoor area features a spacious deck with seating and railing, steps leading to the second floor. Below, a patio area includes tables and chairs, with a kayak resting nearby. Soft lighting accents the space, enhancing the inviting atmosphere of the backyard.

4.66 out of 5 average rating, 32 reviews

Waterfront 4BR 6+Crib 3BA 1Gm, pool, Kayak, Jetski

5 out of 5 average rating, 5 reviews

Beach Vibe-Waterfront-bring BOAT-beach close! Raie

Cottage rentals 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, 182 reviews

Relax Canalside at our Cottage, fast 200mbps wifi

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.

4.99 out of 5 average rating, 154 reviews

PARADISE POINT on Weeki Wachee (Boat Welcome)

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

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, 370 reviews

Kayak Kottage: waterfront, kayaks, bikes, dockage

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.

4.95 out of 5 average rating, 226 reviews

Coastal Cottage Getaway

Lush greenery features prominently in the scene, highlighting various palm trees and colorful flowering plants. The vibrant yellow flowers contrast with the greenery, while a soft lawn extends through the landscape. A sense of tranquility is suggested by the natural setting.

4.96 out of 5 average rating, 129 reviews

A Dream Cottage!!!

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.

4.89 out of 5 average rating, 177 reviews

Weeki Wachee Barefoot Cottage, Waterfront, Kayak’s

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.

4.94 out of 5 average rating, 118 reviews

Weeki Wachee cottage getaway

Cabin rentals with a kayak

4.96 out of 5 average rating, 77 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

4.93 out of 5 average rating, 14 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

4.71 out of 5 average rating, 7 reviews

Cabin in Spring Hill

New Main River Cabin-Kayaks l New Dock l Ladder

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

4.97 out of 5 average rating, 38 reviews

The cabin is situated alongside a calm river, surrounded by lush trees that display various autumn colors. The two-story structure features a spacious deck and balconies, providing outdoor seating areas. The tranquil water reflects the greenery, creating a peaceful natural setting.

Cabin in Spring Hill

River Run Retreat