
Waterfront vacation rentals in Holiday
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Top-rated waterfront rentals in Holiday
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Holiday fun canal home
Fabulous newly remodeled waterfront home on a Gulf accessible canal. Hot tub & patio seating around gas tablefire! New beds w/ adjustable bases. Enjoy: billiard table, sound system throughout, lanai dining + outdoor grill, mini-fridge/sink & seating around a fire pit. Canal amazes w/views of seasonal wildlife: sometimes manatees & jumping mullet! Fish, canoe (1) & kayak (2) w/ lifejackets provided. Also: jetted tub, indoor fireplace, fully equipped kitchen & laundry. Florida favorites nearby.

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

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.

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

Cabin 3 - Nasturtium Nest
Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay. We look forward to seeing you on the Farm!

Nature Lovers Retreat
Relax and enjoy! Welcome to your 3 bedroom 2 bath vacation home. Newly renovated well equipped kitchen, new appliances and laundry room. Perfect for couples or families to make great memories. You can fish, kayak, paddleboat or just sit back and enjoy nature from our dock on Lake Connelly. Very centrally located in the Tampa Bay area and are close to plenty of things to do: Tarpon Springs Sponge docks, Dunedin, Safety Harbor, St. Pete, Honeymoon Island, Fred Howard Park and more

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.

Cozy Beach Home w/Lake view and Kayak!
Enjoy an entire home, completely renovated located in Holiday, w/Lake view to relax and get away from home. Great locations, near beaches, parks, restaurants, Bush Gardens/Tampa. We have full amenities, full kitchen, living area, fenced yard, Lanai, washer, dryer, workstation w/internet access. Places to explore: -St Nicholas Boat Line -Tarpon Springs Sponge Docks -Tarpon Springs Aquarium -Key Vista Nature Park -Anclote Gulf Park -Anclote River Park

*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…

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

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

Waterfront Fishing Paradise
Enjoy waterfront views, private dock, and direct gulf access, you'll experience the best of both worlds, peaceful waterside living, and quick access to endless outdoor activities! Whether you're an avid fisherman, a boating enthusiast, or simply love spending time on the water, you’ll find everything you need to make the most of your time at our home! Excellent snook fishing Sept 15-December! Snook season open till December 1st
Popular amenities for Holiday waterfront rentals
Waterfront apartment rentals

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

Seaside Chic #3 Waterfront Clearwater Beach

↱Riverfront Escape w/included kayaks near dwntwn↰

15 Steps to the Beach! 2 Bedroom Beach Paradise!

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

Walk to the Beach & Free Paddle Boards+ King Bed

Direct Waterfront "The Lily Pad" Walk to Beach

NEW! Amazing Beach & Sunset Views! Fully Renovated
Waterfront house rentals

Waterfront Retreat with Heated Pool, Hot Tub&Dock

Beautiful Home with a Pontoon!

Lakefront home near beaches w/ waterview, pets ok

Waterfront Retreat W / Floating Dock & Kayaks

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Tree House Treasure

Dolphin-Watch Waterway – Pool/Spa Tarpon

Living your dream
Waterfront condo rentals

Lovely Waterview Condo/ heated pool

Waterfront Condo | Steps to Clearwater Beach 2King

Tiki Themed Waterfront Condo on Tampa Bay

Tampa Bay Waterfront Views Rocky Point

Amazing views on beachfront

Walk to Beach, Bars, and Restaurants Nearby

Florida Breeze

Modern Waterfront Condo - Captivating Sunset Views
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$40,111 GYD | G$41,782 GYD | G$41,573 GYD | G$39,275 GYD | G$34,470 GYD | G$39,275 GYD | G$37,813 GYD | G$36,350 GYD | G$34,261 GYD | G$31,963 GYD | G$34,261 GYD | G$38,439 GYD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about waterfront rentals in Holiday

Total vacation rentals
Explore 20 vacation rentals in Holiday

Nightly prices starting at
Holiday vacation rentals start at G$12,535 GYD per night before taxes and fees

Verified guest reviews
Over 1,040 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Holiday vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Holiday rentals

4.8 Average rating
Holiday stays are highly rated by guests—averaging 4.8 out of 5!
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