Holiday rentals with a kayak in Port Richey

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.

4.98 out of 5 average rating, 105 reviews

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, 133 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

4.97 out of 5 average rating, 79 reviews

A spacious living area is furnished with two comfortable sofas and a coffee table, complemented by a decorative rug. Artwork featuring seashells adorns the walls, and a large television provides entertainment. Natural light flows through the numerous windows, enhancing the open atmosphere.

Home in New Port Richey

Waterfront Getaway w/ Dock & Kayaks – Dog Friendly

Welcome to Pelican Cove. Relax in our newly renovated 3-bed, 2-bathroom canal-front home with direct Gulf access and a 12 ft floating dock. Bring your boat or use our included kayaks to explore the stunning coastline, Anclote Key, and local islands. This dog-friendly getaway features smart TVs in every room, a fully stocked kitchen, Wi-Fi, and in-home laundry. Enjoy coffee on the patio overlooking the canal, or grill dinner after a day on the water. *Please check out “other things to note”!*

4.96 out of 5 average rating, 109 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

The outdoor area is illuminated by soft lighting, showcasing a spacious lawn with lounge chairs and a red umbrella. The cozy patio area features seating, creating an inviting space for relaxation. A small dog is seen enjoying the yard, adding a touch of life to the scene.

4.99 out of 5 average rating, 102 reviews

Angele's House, Waterfront with direct Gulf access

Waterfront home with direct Gulf access. 3 bedrooms, 1.5 baths, living room and eat in kitchen. Screened Lanai with BBQ grill. Outdoor Shower. Backyard offers shaded Pergola w/ Gas Grill and seating area. Bring your boat or rent a boat. Public boat ramp located just down the street. Hudson Beach has plentiful inshore fishing Direct gulf access to reefs and wrecks for a day of offshore fishing or Island hopping! Pet friendly w OWNER APPROVAL ONLY, FEES APPLY! We are a non smoking home!

4.96 out of 5 average rating, 113 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.

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.

5.0 out of 5 average rating, 131 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.

An outdoor area features a spacious pool and a hot tub, surrounded by a screened enclosure. Lounge chairs are positioned nearby, offering space for relaxation. Sliding glass doors lead into the house, with a view of additional seating arrangements visible beyond the pool.

5.0 out of 5 average rating, 35 reviews

Wandering Turtles Retreat

Enjoy this beautiful home, designed with relaxation in mind. Fully equipped kitchen, two living spaces and separated bedrooms give multi-family vacations their space. Enjoy the pool and hot tub after a day adventuring in the water nature preserve. We have kayaks and paddleboards to get INTO nature. Our canal is deep enough to park your boat, or you can rent one from a local marina for day fishing adventures. We are here to make you feel at home, while still on vacation.

Guest favourite

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

4.98 out of 5 average rating, 205 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.

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.

4.97 out of 5 average rating, 61 reviews

Lakefront House with Heated Pool

Enjoy your perfect Hideaway in convenient to everything Port Richey. Relax in your private heated pool, or go fishing and kayaking right in your back yard. Central location is a short distances to the activities of Tampa and Clearwater Beach to the south and Crystal River to the North. Two private bedrooms with queen beds, plus a third bedroom with two twins and full laundry. Each room have TV’s. Enjoy the BBQ and gas fire pit, two kayaks and beach accessories.

4.96 out of 5 average rating, 27 reviews

Our Happy Place

Escape to your private waterfront retreat surrounded by stunning state park views. Paddle straight from the house into the bayous and bays of Werner-Boyce Salt Springs State Park. Watch for dolphins, manatees, bald eagles, and more right outside your door. Fish from the dock or kayaks, then unwind on the patio with dinner on the grill and unforgettable sunsets. Prefer a night out? Waterfront restaurants and tropical cocktails are just minutes away.

Guest favourite

A serene waterfront view is captured during sunset, showcasing vibrant hues of orange and pink reflected on the calm water. A palm tree can be seen in the foreground, with a paved pathway alongside the shoreline leading into the distance.