Waterfront Homes for Sale in Holiday, FL

**Waterfront Living • Fully Furnished • Proven 5-Star Short-Term Rental** Whether you're searching for your own waterfront retreat or a turnkey investment opportunity, this beautifully maintained **2-bedroom, 2-bath** home offers the best of both worlds. Being offered **fully furnished (with the exception of artwork and some pieces, list attached) this waterfront gem has operated as a **successful 5-star short-term rental** with a proven rental history, making it an exceptional opportunity for investors while also serving as the perfect full-time residence, seasonal getaway, or vacation home. Buyer should verify local short-term rental regulations and future rental requirements. Inside, you'll find a bright, welcoming interior filled with vibrant coastal colors that perfectly complement the Florida lifestyle. The spacious **waterfront sunroom** provides panoramic canal views and is the perfect place to enjoy your morning coffee, curl up with a good book, or unwind while taking in the shimmering sunset reflections across the water. Step outside into your own tropical waterfront oasis where mature landscaping creates a peaceful, private setting ideal for entertaining family and friends or simply relaxing in the beauty of Florida's waterfront lifestyle. **Looking to maximize the waterfront lifestyle?** Nearby homeowners have enhanced their properties with private fishing docks, offering future owners the opportunity to explore adding their own private dock for fishing, kayaking, paddleboarding, or boating enjoyment (subject to buyer verification, permitting, and local regulations). Major improvements provide added value and peace of mind, including: New Roof(2019), Electrical Updated (2015), New Windows (2022), New A/C System (2023) Move right in or begin generating rental income from day one with this beautifully furnished waterfront property. Whether your dream is peaceful waterfront living or owning a proven income-producing investment, this exceptional home delivers comfort, charm, and endless possibilities. **Come experience the tranquility, beauty, and lifestyle that make waterfront living so special.

4114 Sunray Drive, Holiday

$125,000

1 Beds ⋅ 1 Baths ⋅ Holiday Lake Villas Condo SubDv.

Welcome home to total ease and true maintenance-free Florida living at 3806 Staysail Ln, a beautifully updated, spacious single-story block construction villa in a peaceful 55+ community with no stairs to entry and no unit or neighbors above! Located in a non-flood zone, this home offers added peace of mind before you even step inside. This move-in ready villa has been thoughtfully updated with fresh interior paint, new waterproof LVP flooring throughout, 2019 AC and newer water heater, while the HOA takes care of the exterior maintenance so you can spend more time enjoying life. A reserved covered carport (#3806) is conveniently located directly in front of the villa, with plenty of guest parking available nearby. Large windows fill the home with natural light, creating an inviting atmosphere throughout. The thoughtfully designed floor plan offers room for a full living room set, an eat-in kitchen with newer cabinetry, clean appliances, and bar stool seating at the counter, plus a separate walk-in utility room and an additional outdoor storage room so you'll never run out of space. The washer and dryer are already installed and convey with the home. Unwind in your enclosed Florida room or lanai, open the windows to enjoy the gentle breeze, and take in tranquil pond and fountain views while watching duck families, blue herons, and other birds gather near the water. The oversized primary bedroom features a large walk-in closet, while the spacious bathroom offers a step-in tile shower and plenty of room to navigate comfortably. The low $412/month HOA fee covers water, sewer, trash, cable, internet, roof, exterior building maintenance, exterior painting, lawn and grounds care, and pest control. Outside your door, you can walk to the active clubhouse for card games, bingo, community BBQs, reserve the space for hosting large family gatherings, enjoy the community pool year-round, play shuffleboard, or take a peaceful stroll around the beautifully maintained neighborhood. Conveniently located just minutes from the world-famous Tarpon Springs Sponge Docks, beautiful Gulf beaches, shopping, dining, medical facilities, and everyday conveniences, you'll enjoy the perfect balance of peaceful living and an unbeatable Florida lifestyle. Opportunities to own a beautifully updated, single-story pond view villa in this community don't come along often. Two small pets are welcome, making this the perfect place to enjoy easy, maintenance-free Florida living.

3806 Staysail Lane, Holiday

$275,000

3 Beds ⋅ 3 Baths ⋅ Aloha Gardens SubDv.

Waterfront Fixer-Upper with Incredible Potential! Calling all investors, flippers, and renovation enthusiasts! This 3-bedroom, 3-bath waterfront property sits on a large lot and is packed with opportunity. Whether you're looking to renovate, rebuild, or create your dream waterfront retreat, the possibilities are endless. With a desirable waterfront location and plenty of space to work with, this is a rare chance to unlock significant value. Cash offers only. Don't miss this investment opportunity with outstanding potential!

4138 Star Island Drive, Holiday

$267,900

2 Beds ⋅ 2 Baths ⋅ SubDv.

Virtually Staged. This charming 2-bedroom, 2-bath home with a 1-car garage offers peaceful huge lakefront living with a conservation area across the water, providing exceptional privacy and tranquility. Enjoy fishing or crabbing right from your own spacious backyard, or simply relax and take in the beautiful sunset views over the lake. The house have never flooded during the last two major hurricanes Helen and Milton 2024 as the house is well elevated about 8 feet. Elegant flooring, Remodeled the two bathrooms, Bright house with lots of windows, water electric heater 2025, Garage door 2019, A/C 2017 and roof 2015..Oak kitchen cabinets with St.St appliances. Located in the heart of Holiday, this home combines natural beauty with everyday convenience—perfect for full-time living or a relaxing Florida retreat.This house offers outstanding potential as a short-term vacation rental or long-term investment. Seller will contribute up to $2,000 toward the buyer’s allowable closing costs, prepaids, and/or interest rate buy-down with an acceptable purchase contract.

3340 Wilson Drive, Holiday

$525,000

2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv.

NEVER FLOODED DURING HURRICANE HELENE! This is a rare opportunity to own a Gulf-access waterfront home that offers both an exceptional boating lifestyle and added peace of mind. According to the seller, the home has never experienced flooding or water intrusion, making it an outstanding choice for buyers seeking waterfront living with confidence. Nestled in the highly desirable Baileys Bluff Estates, this move-in-ready waterfront home sits on an oversized 0.31-acre lot with approximately 55 feet of saltwater canal frontage, offering direct Gulf access in about one minute. Bring your boat, kayaks, paddleboards, and fishing gear—your waterfront adventures begin right in your own backyard. Boaters will appreciate the private boat ramp, 10,000-pound boat lift, with, stationary dock, and concrete seawall, making launching and storing your boat effortless. Spend your days fishing, scalloping, island hopping to Anclote Key, or watching spectacular Gulf sunsets just minutes from home. Inside, you'll find an inviting floor plan featuring 2 bedrooms, 1.5 baths, an updated kitchen with solid wood cabinetry, updated bathrooms, comfortable living spaces, and a bright Florida room overlooking the tranquil canal. The home has been well maintained and is ready for its next owner. Major recent improvements provide outstanding value, including a brand-new roof (2025) and a brand-new air conditioning system, helping reduce future maintenance costs while increasing buyer confidence. The spacious backyard provides plenty of room to entertain, garden, or simply relax while enjoying peaceful waterfront views and abundant Florida wildlife. Located just minutes from Anclote River, the Gulf of Mexico, Key Vista Nature Park, the famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, and medical facilities, this home offers the perfect balance of recreation and convenience. Whether you're looking for a year-round residence, seasonal retreat, or waterfront investment, opportunities like this are becoming increasingly difficult to find. No HOA, Move-in ready. Schedule your private showing today and discover why this exceptional Gulf-access waterfront property is one of Holiday's best boating values.

3318 Pineview Drive, Holiday

$90,000

Tahitian Dev SubDv.

Discover the perfect setting for your custom waterfront dream home on this expansive .39-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering ample space for a variety of home designs, outdoor living areas, and landscaping possibilities, this oversized property provides a rare opportunity to create your ideal Florida retreat. An added bonus - the adjacent lot is also available for purchase, allowing for an even larger homesite or future investment potential. Enjoy peaceful canal views and a tranquil setting in an up-and-coming neighborhood with numerous newly constructed homes. According to the owner, the property has never flooded during past storms, providing additional confidence as you plan your future build. With the property line extending into the water, there is potential to add a private dock, creating the perfect spot for fishing, launching kayaks or paddleboards, enjoying nature, or simply relaxing by the water. Whether you're seeking a waterfront lifestyle or a unique homesite with room to grow, this property offers exceptional possibilities. Conveniently located near shopping centers, restaurants, parks, and zoned schools, the property is also just minutes from the J. Ben Harrill Recreation Complex. Historic Tarpon Springs, known for its waterfront dining, unique shops, festivals, and year-round activities, is only about 15 minutes away. Gulf beaches and endless outdoor recreation opportunities are also within easy reach. Don't miss this rare chance to secure a spacious waterfront lot in a growing area and build the home you've always envisioned.

1504 Jackson Drive, Holiday

$90,000

Tahitian Dev SubDv.

Rare opportunity to build your dream waterfront home on this expansive .27-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering beautiful canal views and a refreshing breeze, this property provides the ideal canvas for creating your custom Florida retreat. An added bonus - the adjacent lot is also available for purchase, creating the potential for an even larger homesite or investment opportunity. The property line extends into the water, presenting the possibility of adding a private dock and enjoying direct access to the canal. According to the owner, the lot has never flooded during past storms, offering additional peace of mind. Situated on an up-and-coming street, you'll find numerous newly constructed homes nearby, further enhancing the area's appeal. Conveniently located near shopping centers, restaurants, parks, and zoned schools, the property is also just minutes from the J. Ben Harrill Recreation Complex. Historic Tarpon Springs, known for its waterfront dining, sponge docks, local shops, festivals, and year-round activities, is approximately 15 minutes away. Gulf beaches, boating opportunities, and outdoor recreation are all within easy reach. Whether you're looking to build a primary residence, vacation getaway, or investment property, this waterfront lot offers location, potential, and a unique opportunity to enjoy the Florida lifestyle.

1503 Jackson Drive, Holiday

$325,000

2 Beds ⋅ 2 Baths ⋅ Country Estates SubDv.

Come check out this gorgeous updated waterfront pool home featuring an open, inviting floor plan and serene views of a natural water setting. Designed for both everyday living and entertaining, the spacious layout seamlessly connects the main living areas while showcasing beautiful waterfront vistas throughout the home. Recent updates include: New fencing for added privacy New flat roof Custom island and pantry upgrades New gutters Step outside to your private backyard oasis, where the sparkling pool and tranquil water views create the perfect setting for relaxing or hosting family and friends. Don't miss this opportunity to own a beautifully updated waterfront retreat that combines comfort, style, and exceptional outdoor living.

4704 Koala Drive, Holiday

$3,750,000

Tampa Tarpon Spgs Land Co SubDv.

ISLAND READY FOR DEVELOPMENT - 6.4 Acres- Approved for 87 units, multi- family, ENTITLEMENTS GRANTED, PASCO COUNTY. LOCATED ON BERRY HILL ROAD, HOLIDAY, FL, East of Grand Blvd. Parcel ID 29-26-16-0000-00500-0050 FOREST HILL EAST DEVELOPMENT designated and approved for 87 multiple-family apartment units, waterfront, adjacent to the Anclote River with Gulf access. A rare multifamily development opportunity on a private 6.45-acre island surrounded by water, proposed 87-unit luxury apartment community... Designed as a three-story mid-rise development totaling approximately 96,842 SF, the project features modern construction, water-view patios and balconies, covered entrances, assigned parking and storage, elevators, and a resort-inspired amenity package.... Planned community features include a clubhouse with exercise room, kitchenette, conference room, and office, pool, tiki bar, pavilion, and BBQ area.... Including fishing, kayaking, canoeing, and direct access to the Anclote River with routes to the open Gulf waters and Tarpon Springs.... The property blends privacy, recreation, and upscale design into a truly unique rental concept surrounded by natural beauty. Floor plans, renderings, and site plans available.... Its proximity to Pinellas County, one of Florida's most densely populated counties, enhances its appeal for residential, mixed-use, or investment potential. A rare chance to capitalize on the continued growth and demand along Florida's Gulf Coast.

Berry Hill Road, Holiday

$75,000

Tahitian Homes SubDv.

Rare opportunity to build your dream home on this waterfront lot, situated on a peaceful canal with breathtaking views. With no HOA, you’ll enjoy the freedom to design and build the home that perfectly fits your lifestyle. Boating, fishing, kayaking, sunbathing, the possibilities are plentiful. Conveniently located with easy access to US-19, this property is just minutes from Tarpon Springs Sponge Docks, Fred Howard Park, Anclote River Park, as well as a variety of popular restaurants, shopping, and everyday conveniences. Whether you’re looking to create a full-time residence, seasonal retreat, or investment property, this waterfront lot offers a unique opportunity to enjoy the beauty and tranquility of Florida living. Don’t miss this chance to build and create the waterfront lifestyle you’ve always been dreaming of.

4101 Baden Drive, Holiday

$199,000

2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.

Back on the market!!! Welcome to your own piece of Florida paradise! Enjoy peaceful water views from your screened-in lanai with this spacious 2-bedroom, 2-bathroom waterfront home with no HOA! Inside you will find ceramic tile throughout, with updates including stainless steel appliances in kitchen, and hurricane proof windows/sliding glass doors. Features also include one car garage and newer AC. Home is ready for your personal touches – fantastic opportunity in a convenient location near the Coast!

3531 Landale Drive, Holiday

$799,000

Total of 1.4675 acres, 2 parcels of land. Owner will not sell properties individually. Nestled on the shimmering Anclote River in prime territory in Holiday, Florida. Situated on a waterway that leads out to the Gulf. Located on a coveted cul-de-sac, 200 feet of water frontage is retained by an existing seawall and encircled by trees for privacy. The property has direct views of a conservation island. ALL utilities including city water, power, and sewer are present. A myriad of possibilities are available including subdividing the land into three individual lots (each .48 acres) or retaining the parcel to accommodate a large, single-family home. Zoning permits a SFH structure or a duplex on each lot; one per lot if so desired. For investors or individuals, this prospect offers true flexibility and the chance to acquire a rare stretch in a market hungry for property to support new construction in well-positioned Pasco County. Minutes from: the sparkling Gulf, the culinary delights found in Tarpon Springs, all the retail you need on US Highway 19, and the multi-faceted Anclote River Park offering kayak/fishing access, picnic area, playground, 24/7 boat ramps, recreational courts and more! This nuanced investment suits numerous objectives. Buyer to verify all dimensions, lot sizes, zoning, permitting, leasing restrictions etc.

Flotilla, Holiday

Waterfront Homes for Sale in Holiday, FL

All Waterfront Homes for Sale in Holiday, FL

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