Holiday rentals with a kayak in Port Richey

4.99 out of 5 average rating, 142 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!!

5 out of 5 average rating, 114 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-WeekiWachee River

This charming A-Frame Cedar Cabin is a perfect retreat on the Weeki Wachee River. Families enjoy kayaking, fishing, or relaxing on the dock by the water. In the evening, the atmosphere transforms with underwater lighting and LED dock lights. The cabin features 2 cozy Cedar bedrooms, including one with a spiral staircase and a master suite with water views. The main bathroom has a waterfall faucet and there's a heated outdoor shower nestled in nature. Create unforgettable memories on Weeki Wachee

4.93 out of 5 average rating, 261 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.

4.97 out of 5 average rating, 184 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Apartment in Tarpon Springs

An aerial view showcases a modern two-story house surrounded by water and greenery. A private boat dock is positioned in the foreground, along with a manicured lawn featuring a putting green and colorful kayaks. Solar panels are visible on the rooftop.

5 out of 5 average rating, 102 reviews

Waterfront studio w/Hot Tub and Putting Green

Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size bed and pullout sofa. Microwave, coffee maker, stove top, refrigerator/freezer, 62" Smart TV, gas BBQ. Hot tub (only available from Oct 1st-May 31st) Enjoy the sun, beautiful nature of Anclote River with 3 kayaks and 3 paddle boards. Daily sightings of dolphins, manatees and many species of birds passing by. Fish right off the sea wall. Beach is a short 2-miles away. Overnight boat docking.

4.83 out of 5 average rating, 120 reviews

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.

Home in Hudson

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, 260 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.

Guest suite in New Port Richey

A small outdoor area features a glass-top table surrounded by black metal chairs. Potted plants and vibrant flowers add color to the space with a backdrop of a wooden fence. A section of artificial grass enhances the serene atmosphere.

4.77 out of 5 average rating, 117 reviews

Adorable one bedroom studio near the beach

Forget your worries in this serene and beautiful space. As soon as you enter the cozy courtyard, you can experience the tranquility of your private area. The studio is fully furnished, and kitchen is equipped with everything you need to prepare a delicious meal. Studio is close to stores, restaurants and shops. Enjoy kayaking on the still beaches of New Port Richey. Weeki Wachee Springs State Park is a 25-minute drive away. Downtown New Port Richey is only 5 minutes away.

5 out of 5 average rating, 129 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 Hudson

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, 187 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.

4.98 out of 5 average rating, 99 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!

Two-bedroom waterfront duplex featuring a private floating dock with direct access to the Gulf of Mexico. Take advantage of the battery-operated Jon boat or kayaks and explore the beautiful surrounding mangroves and scenic waterways. The backyard feels like your own tropical paradise. The perfect setting to relax, unwind, and soak in the waterfront views. Enjoy the surround sound music system throughout the property for the ultimate vacation atmosphere.

4.96 out of 5 average rating, 123 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 Port Richey kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

5 out of 5 average rating, 59 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

4.81 out of 5 average rating, 59 reviews

Stunning *Newly Remodeled Riverfront Oasis - Kayak

The image showcases a heated in-ground pool bordered by light-colored pavers, overlooking a calm canal. Docked boats and palm trees line the water's edge, reflecting under a clear blue sky. The well-kept lawn adds a touch of green to the serene waterside setting.

4.71 out of 5 average rating, 179 reviews

Gulf Harbors Getaway Home with Pool

4.99 out of 5 average rating, 89 reviews

A patio area is visible featuring a round table with chairs, surrounded by decorative plants. Kayaks are propped against the railing, while the shimmering water of the canal flows in the background, framed by palm trees and bright blue skies.

Home in Holiday

Nature Lovers Retreat

A serene waterfront view is presented with calm waters reflecting a clear blue sky. Two kayaks in vibrant green and blue are positioned along the shore, while multiple boats are docked nearby. A neatly arranged stone path leads towards the water, surrounded by green grass and landscaping.

4.99 out of 5 average rating, 71 reviews

Beautiful Home with a Pontoon!

4.7 out of 5 average rating, 10 reviews

The home is nestled on a private peninsula, surrounded by tranquil waters, reflecting hues of orange and pink from the sunset. A two-story structure features a balcony overlooking the Gulf, with vehicles parked nearby on a driveway bordered by lush greenery.

Home in Aripeka

Optimystical Vista • Gulf-Front Panoramic Views

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.

4.97 out of 5 average rating, 64 reviews

Waterfront Getaway w/ Dock & Kayaks – Dog Friendly

4.88 out of 5 average rating, 40 reviews

Home in Port Richey

Cozy Oasis Screened Pool Picturesque Canal Views!

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, 184 reviews

Relax Canalside at our Cottage, fast 200mbps wifi

Cottage in Clearwater Beach

4.77 out of 5 average rating, 168 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

4.99 out of 5 average rating, 162 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)

4.85 out of 5 average rating, 20 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

4.94 out of 5 average rating, 98 reviews

A cozy living space features a dark leather couch and a decorative wooden coffee table. Natural light streams through large windows adorned with blue patterned curtains. A flat-screen TV is mounted on the wall, and a wooden cabinet displays nautical-themed decor.

Cottage in Riverview

Cocos Cottage Cottage-Summer fun! 10%off 6/1-8/30

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, 235 reviews

Coastal Cottage Getaway

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, 373 reviews

Kayak Kottage: waterfront, kayaks, bikes, dockage

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, 135 reviews

A Dream Cottage!!!

Cabin rentals with a kayak

4.96 out of 5 average rating, 78 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

4.85 out of 5 average rating, 191 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

4.96 out of 5 average rating, 25 reviews

A private wooden dock extends over calm waters, surrounded by lush greenery. Two kayaks are securely positioned on the dock, ready for adventure. Soft reflective light dances on the water's surface.

Cabin in Riverview

Secluded Riverfront Cabin- kayak, pool table, fish

4.98 out of 5 average rating, 47 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