Waterfront holiday rentals in Holiday

5 out of 5 average rating, 118 reviews

An aerial view captures the A-Frame Cedar Cabin nestled alongside a serene waterway. Colorful kayaks are visible on the dock, while lounge chairs and a paddleboard are arranged on the wooden platform. Lush greenery frames the cabin, enhancing the natural riverside setting.

Cabin in Spring Hill

A Frame Stream Dream-Weeki Wachee

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

4.98 out of 5 average rating, 102 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, 127 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

4.95 out of 5 average rating, 193 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, 104 reviews

Waterfront studio great for Pasco scallop season!

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.

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.

4.96 out of 5 average rating, 103 reviews

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

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.

4.97 out of 5 average rating, 105 reviews

Home in Hudson

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.

A view of Lake Conley is depicted, showcasing calm waters under a clear blue sky. Lush trees line the shore, with a walkway and dock visible on the left, offering access to the water. The scene reflects a tranquil outdoor environment.

4.87 out of 5 average rating, 135 reviews

Waterfront, Sunsets & Heated Pool & Pet Stay Free!

Close to the beach, family activities, public transport, and the Tampa Airport. You’ll love my place because of the ambiance, the outdoors space, the water view, & the sunsets, PRIVATE Heated pool and VERY comfy beds! I provide fishing poles, tackle box My place is great for everyone and furry friends (pets) too!. Third bedroom is Florida room with sliding glass door. Two twin beds and desk. dinning table. Let me know about your pets. Your pets stay free. Totally fenced yard.

A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.

4.95 out of 5 average rating, 80 reviews

*NEW* Riverside Retreat w/Pool

Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…

4.98 out of 5 average rating, 114 reviews

The image captures a serene view of the canal with calm, reflective waters. Lush greenery lines the banks, while several boats are seen docked along the shore. Bright sunlight illuminates the scene, highlighting the tranquility of the waterfront setting.

Home in Palm Harbor

Tarpon Lake Escape LLC

Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.

4.91 out of 5 average rating, 116 reviews

Lakefront Paradise with Heated Saltwater Pool

Discover lakeside bliss at this 2-bedroom retreat with a private pool, dock, and outdoor fire pit. Enjoy stunning waterfront views, relax by the pool, or gather around the fire under the stars. The bedrooms offer a cozy haven, and the fully equipped kitchen ensures convenience. Just minutes from pristine beaches, this retreat provides the ideal balance of relaxation and recreation. Your perfect lakefront getaway awaits!

Popular amenities for Holiday waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Apartment in Clearwater Beach

4.95 out of 5 average rating, 126 reviews

Anchors UP #2, WALK to Beach, 1 bed/1 bath apt.

4.79 out of 5 average rating, 201 reviews

An outdoor space features a wood-burning fire pit surrounded by a cozy seating area. A glass table holds a wine glass, and a calm river reflects the evening sky, dotted with trees along the shoreline. The tranquil atmosphere invites relaxation beside the water.

Apartment in Tampa

Kayaks & Firepit Mins to Dwntwn!

Apartment in Indian Shores

A spacious living area is furnished with two comfortable leather sofas and a wooden side table. A large flat-screen TV is positioned nearby. Natural light floods the room through expansive glass doors leading to a balcony, with ocean views visible in the distance.

4.92 out of 5 average rating, 218 reviews

Direct Beachfront Condo, Ocean balcony view!

Apartment in Indian Rocks Beach

5 out of 5 average rating, 112 reviews

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

Apartment in Indian Rocks Beach

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

4.96 out of 5 average rating, 185 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

4.93 out of 5 average rating, 103 reviews

A covered patio features four comfortable wicker chairs surrounding a glass-top table. Large windows provide views of palm trees and the sunset over the water, creating a serene outdoor space for relaxation.

Apartment in Clearwater

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Apartment in Clearwater Beach

A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.

4.89 out of 5 average rating, 260 reviews

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

Apartment in St. Petersburg

4.95 out of 5 average rating, 142 reviews

Waterfront studio! Heated pool and hottub

Waterfront house rentals

Adirondack chairs are arranged on a pebbled area facing a tranquil canal, with a sunset casting a warm glow over the scene. The serene water reflects the colorful sky, surrounded by lush greenery and residential homes lining the opposite bank.

4.94 out of 5 average rating, 70 reviews

Holiday fun canal home

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.

4.99 out of 5 average rating, 91 reviews

Nature Lovers Retreat

Superhost

A screened-in green room features two wooden chairs positioned around a small table, surrounded by various indoor plants. Natural light streams through the slatted roof, illuminating the view of the river visible through the openings in the walls.

4.83 out of 5 average rating, 93 reviews

Riverside Home with Kayaks

A serene lake view is captured at sunset, with soft colors reflecting on the water's surface. Lush greenery borders the edge, framing the scene and creating a peaceful atmosphere. The silhouettes of trees are visible against the evening sky, enhancing the tranquil setting.

4.87 out of 5 average rating, 46 reviews

Cozy Beach Home w/Lake view and Kayak!

4.93 out of 5 average rating, 125 reviews

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

Home in Palm Harbor

Lakefront home near beaches w/ waterview, pets ok

Superhost

4.57 out of 5 average rating, 7 reviews

Canal-Front Getaway•Poolside Relaxation•Fishing

A vibrant landscape features lush green grass and tropical plants, with a palm tree and bushes in view. A small body of water reflects the blue sky dotted with clouds. An American flag is positioned near a white railing, adding a charming touch to the scene.

4.95 out of 5 average rating, 41 reviews

Relaxing Lake House

4.99 out of 5 average rating, 155 reviews

Home in Hernando Beach

Fire pit, Golf Cart, Kayaks, PedalBoat, Fishing!

Waterfront condo accommodation

4.98 out of 5 average rating, 130 reviews

A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.

Condo in Indian Shores

Relax in a Newly Renovated Beach Front Paradise

4.97 out of 5 average rating, 230 reviews

A vibrant, themed living area features colorful hanging lamps and intricate wall decorations. Lush greenery is present, alongside a mixture of patterned seating arrangements. Large glass doors open to a balcony, allowing natural light to fill the space and offering a view of the outdoors.

Condo in Tampa

Tiki Themed Waterfront Condo on Tampa Bay

4.94 out of 5 average rating, 107 reviews

Condo in Madeira Beach

Beach Front at “The Shore”

4.94 out of 5 average rating, 101 reviews

Condo in St. Petersburg

Top floor condo, water views, private balcony

4.98 out of 5 average rating, 295 reviews

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

Condo in St. Petersburg

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Condo in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 471 reviews

Amazing views on beachfront

4.9 out of 5 average rating, 434 reviews

The image shows a view of the beach, with smooth, sandy shores leading to a row of modern condo buildings in the background. The condos are designed with balconies, featuring multiple stories and large windows, under a clear blue sky.

Condo in Indian Shores

Indian Shores Gulf Front Rental