Holiday Homes for Sale

Holiday Homes for Sale

Welcome to Holiday, Florida, a hidden gem nestled along the stunning Gulf Coast! Known for its warm sunshine, friendly community, and picturesque landscapes, Holiday offers a perfect blend of relaxation and vibrant living. With its proximity to beautiful beaches, local parks, and a plethora of recreational activities, this charming city is ideal for families, retirees, and anyone looking to enjoy the coastal lifestyle.

One of the standout features of Holiday is its affordability. The real estate market here boasts a diverse array of homes for sale, catering to various tastes and budgets. Whether you're searching for a cozy bungalow, a spacious family home, or a waterfront property with breathtaking views, Holiday has something to suit every lifestyle. Many homes feature modern amenities, lush gardens, and easy access to local attractions, making it a great place to settle down.

The community spirit in Holiday is palpable, with numerous events and activities that bring residents together. Enjoy leisurely strolls along the scenic Anclote River or take advantage of the nearby parks for picnics, sports, and outdoor fun. With a variety of shopping and dining options also at your fingertips, you'll find everything you need just a stone's throw away.

If you're dreaming of a home in a welcoming community that offers both tranquility and adventure, look no further than Holiday, Florida. Explore the available homes for sale today, and discover the perfect place to create lasting memories!

Newest Holiday Homes for Sale

2 Beds ⋅ 1 Baths ⋅ Eastwood Acres SubDv. ⋅ 34690 Zip Code

Move in and add your personality to this solid block 2 bedroom Holiday home west of US 19. Situated mid block on a quiet street close to everything a new homeowner needs. This home has been well maintained and features 2 generous bedrooms, one full bath, large family room, kitchen and dining room combo, and a flex room that can be utilized as office space, media room or possibly a guest bedroom. The home also features a 1 car garage with laundry area and fenced back yard. Conveniently located close to major highways 19 and 54, outdoor recreation, night life, shopping, restaurants and a short drive to world class beaches.

3415 Monticello Street, Holiday

3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code

Welcome to this Amazing Waterfront 3-bedroom, 2-bathroom residence, complete with a versatile bonus room! This home features an oversized two-car garage and a wealth of exceptional upgrades. Step inside to find new tile flooring throughout the entryway, kitchen, bonus room, and recent remodeled guest bath. Enjoy the elegance of crown molding and ample closet space, including his and her walk-in closets in the Primary suite. The remodeled baths boast luxurious finishes, with a heated whirlpool tub in the master bath for your relaxation. Safety and convenience are paramount, with hurricane-proof replacement windows and a new garage door. Outdoor living is at its finest with a boat lift, floating dock, and davits, perfect for boating enthusiasts. Dive into your large in-ground pool while enjoying breathtaking views of the Anclote River and the vibrant local wildlife, all set against the backdrop of a wide canal and a high seawall. This home is a true gem for anyone seeking a waterfront lifestyle. Don't miss your chance to make it yours! CALL TODAY FOR YOUR PRIVATE TOUR...

1117 Rushmore Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Tahitian Homes SubDv. ⋅ 34691 Zip Code

Welcome home to this beautifully updated 2-bedroom, 2-bath home in Tahitian Homes with NO HOA! An inviting covered front porch opens to a bright interior featuring wood-look tile flooring, contemporary lighting, and a flowing layout for comfortable living and entertaining. The kitchen showcases crisp white cabinetry, stone countertops, a tile backsplash, and stainless steel appliances. Generously sized bedrooms and tastefully updated bathrooms complete the home’s welcoming feel. Step outside to a spacious backyard with a fenced area and room for outdoor dining, gardening, or simply enjoying the Florida sunshine. Conveniently located near shopping, dining, and US-19, this home also puts coastal recreation within easy reach. Enjoy boating at Anclote River Park, explore the shops and waterfront restaurants at Tarpon Springs’ historic Sponge Docks, or unwind on the beach at Fred Howard Park. Schedule your private showing and discover everything this home has to offer!

4149 Darlington Road, Holiday

3 Beds ⋅ 2 Baths ⋅ Midway Acres SubDv. ⋅ 34690 Zip Code

Just minutes from Tarpon Springs, the Sponge Docks, Fred Howard Park, Gulf beaches, shopping, dining, and everyday conveniences, this updated 3-bedroom, 2-bath Holiday home offers an easygoing lifestyle. Major improvements include a roof in 2016; A/C system in 2019; electrical inspection and upgrades in 2021, including outlets and GFCI protection, plus a newer electrical main panel; septic system improvements in 2022; and a water heater and well-water tank in 2023. Additional updates include a refreshed kitchen and bathrooms, granite countertops, updated appliances, luxury vinyl and tile flooring, blinds, lighting, interior and exterior paint, fencing, gates, and front and rear outdoor living areas. 1,102 heated square feet, the home also features an attached one-car garage, additional carport parking, a private well, a septic system, a fenced yard, and a storage shed. Double wide gates from the street on the South and North side of the home provides convenient access for storing boats, trailer, or other recreational equipment, a great feature for enjoying the Florida Gulf Coast lifestyle. Nearby public schools include Sunray Elementary, approximately 1.4 miles; Paul R. Smith K-8, approximately 2.2 miles; and Anclote High School, approximately 2.5 miles. School zone enrollment eligibility should be independently verified. Located in Flood Zone X, this home combines practical improvements, useful outdoor space, and convenient access to beaches, boating, parks, and some of the area's most popular Gulf Coast destinations.

1408 Jennings Drive, Holiday

3 Beds ⋅ 3 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code

Virtually Staged. IN-LAW suite! Meticulously renovated 3-bedroom, 3-bathroom move-in ready and ready! This stunning home features countless upgrades, including a new HVAC system, smart STAINLESS steel appliances, new kitchen cabinets, sparkling white MARBLE countertops, a smart stainless steel washer and dryer, oversized 24” x 48” TILE flooring, 5-inch baseboards, new doors and trim, newer windows, a newer electrical panel, and fresh interior and exterior paint. Enjoy the bright, open floor plan that seamlessly connects the living and dining areas, enhanced by modern fixtures and recessed lighting throughout. All three bathrooms have been beautifully updated with designer tile and high-end finishes. The spacious primary suite features a walk-in closet, a private en-suite bathroom, and direct access to the backyard. The private mother-in-law suite includes a brand-new mini-split A/C system, a kitchenette with a full-size refrigerator, cooktop, microwave, and sink, a separate entrance, and a full bathroom - making it ideal for guests, extended family, or potential rental income. Outside, you’ll find a brand-new vinyl privacy fence, fresh sod, and decorative landscaping, creating the perfect outdoor space to enjoy. Located in a prime area near the world-famous Tarpon Springs Sponge Docks, the historic Greek community, beautiful Gulf beaches, shopping, dining, and all that the Tampa Bay area has to offer, this truly turnkey home is a rare opportunity you won’t want to miss! One or more photo(s) was virtually staged.

3215 Kilburn Road, Holiday

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code

Fresh updates, a generous corner lot, and an unbeatable price tag make this Holiday Lake Estates home an opportunity too hard to ignore! This 2-bedroom, 1.5-bath home welcomes you with a recently renovated interior featuring LVP Flooring, natural light, and a modern kitchen with white shaker cabinetry, tile backsplash, and stainless steel appliances (2024). French doors open to the screened back patio, creating an inviting spot for indorr/ outdoor living. The large corner lot offers space to garden, entertain, and enjoy the outdoors, while a one-car garage adds practical parking and storage. Beyond your doorstep, explore nearby Key Vista Nature Park, launch a boat or kayak at Anclote River Park, or head to the Tarpon Springs Sponge Docks for waterfront shops and Greek dining. Convenient access to US-19 keeps everyday shopping and restaurants within reach. With an updated interior, usable outdoor space, and an accessible price point, 2055 Norfolk Drive brings together the features that make owning a home feel within reach. Schedule your showing and see how much this home has to offer!

2055 Norfolk Drive, Holiday

4 Beds ⋅ 4 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

Welcome to your dream waterfront estate in the sought-after Baileys Bluff community! This stunning custom mini mansion is perched high and dry with no HOA, offering unparalleled privacy and luxury. Enjoy direct Gulf access with a new dock equipped with electric and water, a seawall, and a serene backyard oasis featuring a lagoon-style saltwater pool, spa, waterfall, expansive Belgard paver deck, outdoor shower, travertine rear porch, and cedar trellis dining area—all with no rear neighbors. Step inside to soaring 10-14 foot ceilings, nine sets of French doors, and rare Santos Mahogany floors that exude timeless elegance. The chef’s kitchen is a masterpiece with granite counters, custom cabinetry, a large island, and a high counter perfect for entertaining. The first-floor primary suite is a true retreat with dual walk-in closets, private pool access, and an opulent spa bath with whirlpool tub and dual shower. Upstairs features a full secondary residence with three bedrooms, two baths, a massive living area, balcony with stunning sunset views, and a second laundry. The home also includes three spacious porches, a four-car garage with 14-foot ceilings, a six-inch slab, lift potential, and abundant workshop space. Luxury upgrades include impact windows, full hurricane strapping, exterior insulation, three new AC systems (2024), and a new tankless water heater. Baileys Bluff offers a community boat ramp, clubhouse, and parks, with nearby Anclote boat launch, marinas, waterfront dining, and the world-famous Tarpon Springs Sponge Docks accessible via quiet neighborhood roads. This estate blends sophistication, comfort, and waterfront living in one spectacular package.

3143 Pineview Drive, Holiday

3 Beds ⋅ 1 Baths ⋅ Midway Acres SubDv. ⋅ 34690 Zip Code

LOCATION, UPDATES & FLEXIBILITY! Welcome to this beautifully updated and completely remodeled 3-bedroom, 1-bathroom home in a fantastic Holiday location with convenient access to Pinellas County and everything the Tampa Bay area has to offer! Step inside to find a fresh, move-in-ready interior featuring brand-new laminate flooring installed throughout the home. The fully updated galley-style kitchen is equipped with modern stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The home offers three bedrooms, with the third bedroom created from a portion of the garage. For buyers who prefer additional garage space, this area can easily be converted back, providing valuable flexibility to suit your needs. Additional highlights include a newer roof, newer A/C, interior laundry room, spacious backyard, and ample driveway parking. The large backyard provides plenty of room for entertaining, gardening, pets, or simply relaxing and enjoying Florida’s beautiful weather. Conveniently located near parks, beaches, shopping, restaurants, medical facilities, and major conveniences, this home offers the perfect combination of comfort, updates, location, and versatility. Don’t miss this opportunity to make this move-in-ready Holiday home your own. Schedule your private showing today!

1400 Jennings Drive, Holiday

2 Beds ⋅ 1 Baths ⋅ Tahitian Homes SubDv. ⋅ 34691 Zip Code

WELCOME HOME to this charming and MOVE-IN READY 2-bedroom, 1-bath home located on Beachwood Drive in Holiday, Florida! Tucked away on a NON-THROUGH STREET with limited traffic, this well-maintained home offers a comfortable, functional floor plan along with numerous updates throughout. Major improvements include a 2025 A/C, NEWER WINDOWS, a newer garage door and an updated water heater. Step inside to a bright and inviting interior featuring UPDATED FLOORING, fresh paint and large windows that bring in plenty of natural light. The traditional layout provides defined KITCHEN, DINING and FAMILY ROOM spaces, creating an easy flow for everyday living. Both bedrooms offer generous windows, while the UPDATED BATHROOM features newer tile and an updated vanity. The kitchen has also been refreshed with UPDATED CABINETRY AND COUNTERTOPS, providing a clean and functional space for cooking and entertaining. Even the sliding glass door has been replaced and opens to the backyard, where you'll find a spacious outdoor area and BACK DECK perfect for relaxing, grilling or enjoying the Florida sunshine. A welcoming FRONT PORCH adds even more outdoor living space. With its updated mechanicals, newer windows, refreshed interior and convenient Holiday location, this 2-bedroom Florida home is ready for its next owner!

3811 Beechwood Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Siesta Terrace First Add SubDv. ⋅ 34690 Zip Code

Short Sale. Great Opportunity in Holiday, FL – Short Sale Property! This single-family home offers fantastic potential for investors, primary buyers, or anyone looking to customize a home to their liking. 2 Bedrooms & 1.5 Bathrooms, Comfortable lay-out with great functional space. A bright and spacious Florida room, perfect for relaxing, entertaining, or enjoying sunny days indoors. Versatile extra room that can easily serve as a home office, playroom, den, or guest area. Additional outdoor shed/storage building providing plenty of space for tools, equipment, or extra belongings. Features a charming exterior design with nice accent stone, a welcoming front porch, and plenty of yard space.

1918 Villa Rosa Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv. ⋅ 34691 Zip Code

Enjoy peaceful pond views and effortless Florida living in this beautifully updated, move-in-ready home in Holiday! From the stylish interior to the tranquil waterfront setting, this home offers an inviting place to relax, recharge, and feel right at home. The stunning kitchen features high-end cabinetry and elegant granite countertops, creating a beautiful space for everyday cooking and entertaining. Both bathrooms have been tastefully remodeled with contemporary vanities and stylish finishes. Thoughtful updates include a newer AC unit and ductwork, washer and dryer, gutters, garage door, and front entry door—adding comfort, convenience, and curb appeal. The true highlight awaits out back, where picturesque pond views provide a relaxing backdrop to your day. Enjoy your morning coffee by the water, cast a fishing line, or simply unwind while taking in the peaceful surroundings. This is the Florida lifestyle you’ve been looking for! Conveniently located just a short drive from Tarpon Springs, you can explore the historic Sponge Docks, enjoy delicious Greek dining, and discover charming local shops. Gulf Coast beaches and convenient airport access put recreation and travel within easy reach. Beautiful updates, a serene pondfront setting, and a convenient location—this home is ready for you to move in and start enjoying it all. Schedule your private showing today!

3532 Overland Drive, Holiday

2 Beds ⋅ 1 Baths ⋅ Holiday Lakes West SubDv. ⋅ 34691 Zip Code

Charming 2-Bedroom Retreat in Holiday, FL - Simple Living at Its Finest! Welcome to 1238 Fuchsia Dr., a delightful single-family home offering 1,012 square feet of thoughtfully refreshed living space with 2 bedrooms and 1 bathroom, NO flood zone. Priced to sell and move-in ready, this home is the definition of comfort and simplicity. Step inside and be greeted by a bright, inviting living room where natural sunlight pours through the front window, creating a warm and welcoming atmosphere. The kitchen is a true highlight, featuring abundant cabinet and counter space along with sleek, new stainless steel appliances, new SS refrigerator. The spacious layout flows seamlessly into the dining and family rooms, all grounded by easy-care off-white tile flooring, while brand new oak colored vinyl floors add a fresh, modern touch to the living room and hallway along with all new doors leading into each bedroom. Both bedrooms are cozy and comfortable, complete with brand new carpet and built-in closets for convenient storage. The sunroom has been completely redone with all new dry wall adding an additional living space for the home. The bathroom has been beautifully redone, including a brand new toilet. The laundry room comes equipped with a dryer and ample storage cabinets for extra organization. Additional features include: 1-car attached garage, AC replaced in 2021 is equipped with a whole home air purification system, Fresh interior paint throughout, Fenced-in yard with chain link fencing, No HOA - true freedom of ownership. The area has so much to do with many shops near by and having access to the US Highway 19 you are only minutes away from shopping, cultural events, golf courses, amusement parks, multiple world renown beaches and minutes away from Tampa & St. Pete airports. Homes like this, offering space, updates, and unbeatable value - don't stay on the market long. Contact the listing agent today to schedule your private showing!

1238 Fuchsia Dr. Drive, Holiday

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