Holiday rentals with a kayak in Hudson

4.99 out of 5 average rating, 150 reviews

Home in Hernando Beach

Fire pit, Golf Cart, Kayaks, PedalBoat, 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.

4.89 out of 5 average rating, 110 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.

4.98 out of 5 average rating, 101 reviews

A warm glow from a fire pit illuminates the backyard, surrounded by lush greenery and palm trees. A deck adorned with string lights can be seen in the background, under a night sky featuring soft clouds and a bright moon.

Home in Port Richey

Waterfront home w/dock-Kayaks & Jon Boat included!

Escape to this charming two-bedroom waterfront duplex, complete with a floating dock offering direct access to the Gulf of Mexico. Spend your days exploring the area's picturesque mangroves and scenic waterways using the provided battery-powered Jon boat or kayaks. Step outside to a backyard that feels like your own tropical retreat. A surround-sound music system extends throughout the property, creating the perfect atmosphere for entertaining, lounging, or simply soaking in the vacation vibes

4.96 out of 5 average rating, 125 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 the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Superhost

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, 120 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

4.98 out of 5 average rating, 265 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.

4.95 out of 5 average rating, 213 reviews

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.

Home in Hernando Beach

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)

A cozy, newly remodeled home is presented with a welcoming front entry and a small, landscaped yard. The light-colored exterior is complemented by large windows and a front porch with steps. A mixture of trees and greenery surrounds the property, contributing to the tranquil setting.

4.95 out of 5 average rating, 85 reviews

Cozy House With Large Deck

LOW CLEANING FEE! Take it easy at this unique and tranquil getaway. Newly remodeled originally a mobile home features three bedrooms with the master bedroom that leads out to the back deck. Open the curtains to start your morning and enjoy the sunrise on the deck as you watch all the wildlife. Manatee are known to pass by as they frequent in the warm spring waters about 100 yards away. House features 2 adult kayaks and 2 youth kayaks so you can enjoy the canal and spring as you wish.

4.97 out of 5 average rating, 101 reviews

45% OFF- Pet friendly, waterfront, kayaks, fishing

• Private boat dock & floating dock – Bring your boat and keep it secured in the water! • Kayaks included – Explore the scenic canals and nearby waterways. • Tiki hut – Kick back in the shade with a cool drink. • Fenced in backyard - Paved and fenced in backyard. • Fishing right from the backyard – Cast a line and see what you can catch! • Spacious outdoor seating – Enjoy sunset views and coastal breezes. • Immediate access to the Gulf of Mexico - A short boat ride away.

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.

4.87 out of 5 average rating, 82 reviews

SunWild Ventures Home *Golf Cart & Kayaks*

Relax with the whole family at this peaceful place to stay. 2 Bedroom, 2 Bath home on the water with floating dock (cleats available to tie your personal boat up to) and Kayaks located on a canal with direct access to the Gulf of Mexico. This home has a beautiful back yard on the water for fishing, entertaining, grilling out, and relaxing by the firepit (propane). Also included is a golf cart to tour the golf cart friendly town of Hudson, with many restaurant's to choose from.

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.

5 out of 5 average rating, 129 reviews

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.