Holiday Homes For Sale & Real Estate - 253 homes

Remarks: Welcome to this well-cared-for home in the Forest Hills community of Holiday, offering a great combination of updates, functionality, and outdoor space. With a comfortable layout and natural light throughout, this home is ideal for everyday living or investment.The interior features a bright living space and an updated kitchen that adds a modern touch while keeping things practical. The layout flows easily, making the home feel open and inviting.Step outside to a fully fenced backyard with southern exposure, providing sunshine throughout the day. This space is perfect for pets, entertaining, gardening, or creating your own outdoor retreat or future pool area.Several major improvements have already been completed, including a septic system approximately 5 years old, roof approximately 9 years old, A/C approximately 10 years old, windows approximately 10 years old, and a hot water heater just 1 year old, offering added peace of mind. Conveniently located near shopping, dining, beaches, and main roadways, this property offers both comfort and accessibility. Whether you are looking for a primary residence, seasonal home, or investment opportunity, this is a solid choice. Schedule your showing today and see the value for yourself.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ellie Lambert (813-690-0319)

Remarks: Beautiful property featuring stunning lake views and breathtaking sunsets. The spacious and pleasant backyard is perfect for enjoying time with family and friends, ideal for outdoor gatherings and barbecues. This home is move-in ready and offers bright, open living spaces, including a living room and dining area. It also features a cozy family room with lake views, custom built-in wooden cabinetry, and an elegant electric fireplace—perfect for enjoying during the cooler months. A unique opportunity to live in a peaceful setting that combines comfort, functionality, and an exceptional view.

Listing is courtesy of: LCA REALTY, LLC (813-451-2197)

Listing Agent: Druselis Escalona (305-924-7629)

Remarks: Spacious 2-bedroom home offering 1,507 sq ft of living space, featuring a converted 2-car garage ideal for a potential 3rd bedroom, office, den, or family room. This versatile space includes exterior door access and large windows, delivering great natural light and flexibility. Updated windows and doors (2016) enhance energy efficiency and overall appeal. Roof replaced in 2019. Located in Zone X – no flood insurance required. Packed with potential, this home is the perfect canvas to create your own Florida retreat. With just cosmetic updates, you can unlock serious value and customize the space to fit your lifestyle or investment goals. Opportunities like this—offering size, flexibility, and upside—don’t come around often.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Denise Bram (813-323-1949)

Remarks: Beautifully updated 3-bedroom, 1.5-bath home in the heart of Holiday featuring a one-car garage and a brand-new 2025 roof. Recent upgrades include new windows, updated electrical work and plumbing, new flooring throughout, a newly renovated bathroom, and a new irrigation system. The kitchen has also been updated with new cabinets, butcher block countertops, and stainless steel appliances. Enjoy a spacious fenced backyard perfect for relaxing or entertaining. Located in a non-flood zone and close to shopping, dining, and major roadways.

Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)

Listing Agent: Marcel Driver (727-656-3325)

Remarks: One or more photo(s) has been virtually staged. Welcome to 5313 Boardwalk Street — a beautifully updated 3 bedroom, 2.5 bath waterfront home offering incredible value in one of Holiday’s most desirable boating communities. This property experienced no flood damage from past hurricanes, providing peace of mind while enjoying true Florida waterfront living. Major systems have also been updated, including a 2021 HVAC system, adding comfort and efficiency for years to come. Out back, you’ll find a covered 10,000 lb boat lift plus a wet slip accommodating up to a 30’ vessel, making this home ideal for serious boaters. From your dock, enjoy easy navigation to the Gulf of Mexico, with multiple waterfront restaurants, marinas, and live music spots along the way. With world-class fishing and diving off Anclote, this truly is a boater’s paradise at an incredible price point. Inside, the home showcases tasteful updates and modern finishes throughout. The open layout features vaulted ceilings creating a bright, airy feel, stainless steel appliances, granite countertops, upgraded backsplash, modern fixtures and finishes, and an inside laundry room. The screened balcony overlooking the canal is a standout feature — the perfect place to enjoy sunrise coffee or unwind at sunset with a waterfront view. Downstairs, you’ll appreciate the huge garage with nearly 400 sq ft of additional storage space under the home, providing ample room for water toys, fishing gear, and all your boating essentials. If you’ve been searching for Gulf access, a private boat lift, updated interior finishes, and strong system updates — this home checks all the boxes. Schedule your private showing and start living the waterfront lifestyle. Flood Insurance only $826/year!!

Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)

Listing Agent: Jonathan Hernandez (727-417-1122)

Remarks: Under contract-accepting backup offers. NEW ROOF INSTALLED MARCH 2026, MOVE-IN READY | NO HOA | NO FLOOD INSURANCE REQUIRED. STOP SEARCHING! This impeccably updated 3-bedroom, 1-bathroom home in the heart of Holiday is the unicorn you’ve been waiting for. Enjoy the ultimate freedom of NO HOA and NO CDD fees, plus the massive savings of NO flood insurance required! Step inside to a bright, open floor plan flooded with natural light that leads you to a fully updated kitchen featuring modern finishes and ample storage. The practical layout has a seamless flow, perfect for first-time homebuyers or savvy investors looking for a low-maintenance rental. The exterior is a true private oasis with a fully fenced yard—ready for your pets, gardening, or weekend BBQs. Parking is a breeze with a 1-car garage and two additional driveway spaces. Located just minutes from world-class beaches, parks, and major shopping, this home offers the perfect balance of a quiet residential feel and urban convenience. Newer upgrades and a pristine interior mean you can move in today and start living the Florida lifestyle tomorrow. Schedule your private tour before it’s gone!

Listing is courtesy of: LA ROSA REALTY, LLC (407-592-4667)

Listing Agent: Lilibeth Garcia (727-717-4152)

Remarks: One or more photo(s) has been virtually staged. Welcome to 2211 Barracuda Ct, Holiday, FL 34691 — a beautifully maintained turn-key home offering 1,876 sq ft of living space in the desirable Gulf winds community. This home features 3 bedrooms, 2 full bathrooms, plus a bonus room that can be used as a home office, playroom, media room, or flex space. The home is also pre-wired for a home theater system, making it perfect for movie nights and entertaining. the bright, open floor plan is filled with natural light and flows into the open kitchen featuring wood cabinetry, stainless steel appliances, pantry storage, and a breakfast bar, ideal for everyday living and gatherings. A separate dining area provides additional space for family meals. The primary suite offers a relaxing retreat with a walk-in closet, dual vanities, a soaking tub, and a separate walk-in shower. Two additional bedrooms are generously sized and conveniently located near the second full bathroom. Enjoy Florida living from the screened lanai, overlooking a peaceful, low-maintenance outdoor space. Additional highlights include a 2-car garage, indoor laundry room, water softener system, and key updates such as AC (2018), water heater (2011), and a new garage door (2025) providing comfort and peace of mind. It is conveniently located near shopping, dining, parks, and major roadways. This move-in-ready home is a must-see — schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)

Listing Agent: Mayra Roland (727-742-8588)

Remarks: Beautifully and completely remodeled 3-bedroom, 2-bath home located in a desirable Holiday neighborhood. This move-in-ready residence features a thoughtfully updated interior with modern finishes, new impact-resistant windows, an open, functional layout, and abundant natural light throughout. The updated kitchen offers modern cabinetry, sleek countertops, and flows seamlessly into the living and dining areas—perfect for everyday living and entertaining. Also the water heater and electric pannel are in great conditions from 2023 and 2024. The spacious primary suite includes a private, updated bathroom, while two additional bedrooms provide comfort and flexibility for family, guests, or a home office. Both bathrooms have been tastefully renovated with modern fixtures and finishes. Conveniently located near shopping, dining, schools, parks, and major roadways, this home combines style, comfort, and location. A fantastic opportunity to own a fully remodeled home—schedule your showing today!

Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)

Listing Agent: Enid Izquierdo (813-965-2120)

Remarks: A Private, Park-Like Oasis with Unmatched Amenities Awaits! If you are afraid of nature, this might not be for you. Discover an unparalleled retreat where natural beauty meets modern convenience. Looking out at mature, leafy trees, this remarkable property features a serene pond and small stream. Sit by your firepit or cross over your charming bridge inviting serene moments of quiet reflection. Inside, the kitchen inspires the home chef with granite counter tops and modern appliances that include a double oven and island mounted electric cook top with exhaust. The inviting living space boasts a warm and cozy stone veneer fireplace, ideal for relaxing on crisp evenings. This property is an outdoor enthusiast's dream, offering extensive functionality with a workshop, a spacious RV or boat carport for your adventures, and a generous two-car garage. This rare opportunity offers a lifestyle of comfort, privacy, and endless possibilities. The city of Holiday is known for its proximity to the Tampa Bay area, but with a more quiet budget friendly cost of living and a focus on parks and nature, including the Anclote River Park and Key Vista Nature Park. Don't miss your chance to own this one-of-a-kind gem—schedule your private showing today!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Bill Whiteside (813-748-8804)

Remarks: Under contract-accepting backup offers. This 2-bedroom, 2-bath home on a quiet and cozy cul-de-sac in Holiday is proof that smart updates and thoughtful design make all the difference. From the start, it delivers easy living with a maintenance-free front yard, no grass, no mowing, no weekends lost. Inside, the layout feels open, bright, and refreshingly functional. The living space flows naturally throughout. The Florida room could easily be converted to a 3rd bedroom. The kitchen is a standout for this style of home. Its unique open configuration features wraparound counters, stainless steel appliances, warm wood cabinetry, and pendant lighting perfectly positioned for hosting, multitasking, or keeping conversations going while you cook. Both bedrooms are comfortably sized and feature brand-new carpet and baseboards, adding a fresh, move-in-ready feel. Two full bathrooms and a layout that simply works make this home easy to love and easy to live in. Additional highlights include a garage plus covered carport, a low-maintenance exterior, and for peace of mind, a roof replaced in 2023—a major update already checked off the list. Whether you’re buying your first home, downsizing, or just looking for something clean, comfortable, and well cared for, this one delivers practicality with personality. Schedule your showing today.

Listing is courtesy of: JAY ALAN REAL ESTATE (855-529-2526)

Listing Agent: Samantha Greene (727-485-3665)

Remarks: Your wish is granted! Don’t miss this opportunity to own a beautifully maintained 3-year-old townhome in Holiday, FL. This move-in ready 3 bedroom, 2 1/2 bath home comes complete with smart-home devices for your convenience. Step outside and enjoy the peaceful pond just beyond your backyard, where you’ll often see an assortment of ducks, the occasional sandhill crane, and even a seasonal flock of robins. With its contemporary design, low maintenance, and prime location, this home is perfect for anyone looking to settle into comfort and style. Schedule your showing today! ***New sod just put down***

Listing is courtesy of: FLORIDA HOMES RLTY & MORTGAGE (904-996-9115)

Listing Agent: Jacob Maisel, Iii (727-512-8451)

Remarks: Enjoy Comfortable Florida Living in a Welcoming 55+ Community Retire in comfort and embrace the tranquil Florida lifestyle in this beautifully maintained 1-bedroom, 1-bath home, located in a friendly 55+ land-owned community with no lot rent. This charming residence is offered fully furnished, with most contents included—essentially what you see is what you get. The home has benefited from numerous renovations, including a completely updated Florida room, kitchen, bathroom, screened-in lanai, and rear patio. The driveway has been widened to accommodate your car and a golf cart, adding both convenience and functionality. The Florida room can easily be converted into a second bedroom, making it ideal for visiting guests. Exceptional curb appeal welcomes you home, while the large covered, screened-in lanai provides the perfect space to relax and enjoy Florida’s sunshine. All backyard patio and screened lanai furniture are also included. This active community offers amenities designed for relaxed, social living, including a heated pool, clubhouse with planned activities, lawn care, and trash service, all covered by a low HOA fee. The home is within walking distance of the community pool, enhancing its appeal. Whether you are a seasonal snowbird or planning to retire full-time, this move-in-ready, low-maintenance home offers affordable living in a peaceful setting. Sold As Is. Measurements are approximate. All information is deemed reliable but should be independently verified by the buyer.

Listing is courtesy of: MCCULLOUGH & ASSOC REALTY INC (727-237-4940)

Listing Agent: Sophia Arcese (727-744-2226)

Remarks: Imagine stepping into your own slice of sunshine, a darling, move-in-ready home in Holiday, Florida, that feels like a warm hug from the moment you arrive. This charming single-family residence, with its fresh interior and exterior paint, welcomes you with bright, inviting spaces and thoughtful updates throughout. Nestled in a prime location, you're just minutes from multiple beautiful beaches and state parks, including Fred Howard Beach, Sunset Beach, and Anclote Park, all within a quick 15-minute drive. Craving city convenience? Tampa International Airport is an easy 40-minute drive away, making travel effortless while keeping you close to the relaxed coastal vibe you crave. Inside, you'll find two generously sized bedrooms and an updated full bathroom, plus brand-new carpet underfoot for that fresh, cozy feel. The updated kitchen invites you to linger over morning coffee at the counter, while the dedicated indoor laundry room (conveniently housed in the partially converted one-car garage) offers excellent flexibility, it could easily be converted into a second full bathroom using the existing plumbing lines. Need the full garage back? Just remove the wall; the flexibility is built right in. Major mechanicals have been recently updated for true peace of mind: a 2022 roof, 2021 HVAC, a brand-new 2026 water heater, and a new garage door (installed 2021). No surprises here, just reliable comfort waiting for you. Step outside and discover your own private retreat. A fully fenced backyard offers space to play, garden, or unwind, while the covered back patio is perfect for evening breezes, weekend barbecues, or simply watching the sky change colors. Best of all, this patio could be enclosed to create approximately 250 sq ft of additional living space, giving you the option to expand the home and increase its value with minimal effort. The photos say it all, this home is as cheerful and welcoming as it looks. This property is perfect for first-time homebuyers looking to plant roots, savvy investors seeking strong rental potential, or snowbirds wanting an affordable, low-maintenance coastal getaway with no HOA or deed restrictions. It's low maintenance, thoughtfully updated, and full of potential to create beautiful memories for years to come, all while enjoying easy access to Gulf beaches, parks, and Tampa Bay area amenities. Come see how this home can feel like yours. Your story begins here…

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Jessica Christianson (719-229-1763)

Remarks: Under contract-accepting backup offers. This meticulously maintained home offers a spacious, open floor plan highlighted by a generous living room that provides comfortable everyday living and entertaining space. Step outside to the covered back patio—perfect for enjoying your morning coffee or an evening beverage in the Florida breeze. The fully fenced backyard adds privacy and functionality and includes a convenient medium-sized shed for additional storage. Perfect Florida Winter Retreat or Year-Round Residence! Escape the cold and embrace a warm, low-maintenance lifestyle in this beautifully updated 2-bedroom, 2-bathroom home, ideal for seasonal living or full-time enjoyment. Enclosed porch can be used as a bedroom or bonus room.

Listing is courtesy of: 365 REALTY GROUP INC (941-500-4511)

Listing Agent: Teresina Anzalone (352-238-2942)

Remarks: Welcome home to this exceptional 3 bedroom, 2 bath villa with a 2 car garage, located in the highly desirable Gulfwinds community of Holiday, perfectly bordering Tarpon Springs. Offering 1,740 square feet of beautifully designed living space, this home stands out as one of the best villas in Gulfwinds, with too many updates to list. Enjoy maintenance free living, including exterior upkeep, and a paver border driveway that adds instant curb appeal. Inside, the home features tile flooring throughout, a freshly painted interior, crown molding, tall baseboards, and plantation blinds, creating a bright, modern, and cohesive look. The remodeled kitchen is a true centerpiece, showcasing a huge island, granite countertops, and modern stainless steel appliances, perfect for entertaining and everyday living. Numerous big ticket upgrades provide peace of mind, including impact windows, a hybrid HVAC system, water softener, new bathroom faucets, and intelligent home features. Step outside to your brand new lanai, enhanced with expansive pavers inside and out, creating a private patio area ideal for relaxing, entertaining, or enjoying Florida’s outdoor lifestyle. The backyard patio offers excellent privacy, a rare find in villa living. Gulfwinds residents enjoy access to a community pool and an unbeatable location close to the world famous Tarpon Springs Sponge Docks, Sunset Beach, Fred Howard Park, outstanding restaurants, shopping, and more. Convenient access to Tampa, major highways, and the airport makes commuting simple and efficient. This move in ready home combines extensive upgrades, privacy, and an unbeatable location and outstanding opportunity in Gulfwinds.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Costa Sotiriou (727-488-8222)

Remarks: This property truly stands out from the rest! Boasting rich, bold colors, gorgeous styling, beautifully thought out finishes, and exquisite attention to detail, you won't want to miss this 2 bedroom, 2 bathroom, 2 car garage home. As you arrive, you will immediately notice the wonderful charm and curb appeal of this home. The mature trees in the front yard provide a beautiful shade canopy and the covered front patio is the perfect sitting place to enjoy your morning coffee while bird watching. If your lucky you will get a visit from the local sandhill cranes as they pass through the front yard. Upon entering the home through the double front doors, you are met with a spacious open floorplan. The floor to ceiling front windows and French doors along the back allow the beautiful natural light to flow into the large open living space. The kitchen area is the central gathering place for the home, featuring an oversized center island with granite countertop and built in wine cooler/ beverage station leading into the kitchen with beautiful solid wood cabinets, high end stainless steel appliances, elegant granite countertops, large breakfast bar, and extra large, luxury vinyl plank flooring throughout the home. This home features a split plan layout with the large master bedroom on one side with its own large walk in closet and full size ensuite bathroom with tub, and the guest bedroom on the opposite side of the home just outside the spacious full sized guest bathroom with tub. Both bedrooms have durable, low maintenance, extra large, luxury vinyl plank flooring and both bathrooms have beautiful natural stone travertine tile. Enjoy your spacious air conditioned indoor laundry room with a separate wash sink and beautiful natural stone travertine tile. Two sets of French doors lead out to the private, spacious, screened in back porch, where you can ease away the stress of the day by taking a soak in the heated, 6 person hot tub. A third set of French doors through the dining room lead out to your large, private back yard patio. With its mature landscaping and lovely palm trees, your back yard is your own private tropical oasis. Whether you're enjoying a night by the firepit on the patio or relaxing in the spacious above ground swimming pool, the back yard space is perfect for entertaining friends and family or just enjoying time alone. The 2 car oversized garage and extra wide extended front driveway allow plenty of room for your parking and storage needs. Keep your boat or RV tucked away in your own back yard with the convenience of a rear driveway. Need additional storage? The attached shed allows for all those extra items. No HOA and no need to worry about rear neighbors, the county owned conservation land ensures your only rear neighbors will be the egrets, ospreys, herons, and sandhill cranes that frequent the area. Anclote boat ramp is just minutes down the road with direct access to the Gulf. There are several nature parks nearby including: Key Vista Nature Park, Anclote Gulf Park, Eagle Point Park and Robert K Rees Memorial Park. Enjoy a nice walk or bike ride through the Coastal Anclote trail just down the road. The home is centrally located to Tampa, Tarpon Springs, Dunedin, Clearwater, and New Port Richey. Come see this beauty today!

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

Remarks: Welcome home! This beautifully renovated 3 bedroom, 1.5 bathroom home with a 1-car garage is located in one of Holiday’s most desirable neighborhoods. Step inside to find new LVP flooring which is both stylish and easy to maintain. The kitchen is a true highlight, featuring brand new stainless steel appliances and granite countertops. Enjoy Florida living in your spacious backyard, complete with a large screened-in patio perfect for relaxing or entertaining. Just minutes away, you can explore the famous Tarpon Springs Sponge Docks, or take a short drive to the Dunedin Causeway, Honeymoon Island, and world-renowned Clearwater Beach. Conveniently close to shopping, dining, and more. This move-in ready home also comes with a recent survey and a clean 4-point inspection for peace of mind.

Listing is courtesy of: GREAT WESTERN REALTY (813-833-8394)

Listing Agent: Stephanie Schwartz (727-479-4979)

Remarks: Welcome to this beautifully updated one-story home offering 3 bedrooms, 2 full bathrooms, and a 1-car garage, perfectly situated on a quiet dead-end street for added privacy and minimal traffic. This move-in ready property has been thoughtfully renovated throughout, making it an ideal option for both homeowners and investors alike. Step inside to discover a bright and inviting interior featuring brand-new flooring throughout, all new interior doors, and modern finishes that create a fresh, cohesive look. The fully renovated kitchen is a standout, showcasing stylish white cabinetry, sleek quartz countertops, and recessed lighting—perfectly designed for both everyday living and entertaining. Both bathrooms have been completely updated with contemporary finishes, offering a clean and modern feel. Major system upgrades provide peace of mind, including a new AC system and a newer water heater. Enjoy relaxing mornings or evening gatherings in the enclosed covered lanai, adding valuable indoor-outdoor living space. Additional upgrades include new window blinds throughout the home for a polished, move-in ready touch. Conveniently located within walking distance to the elementary school and Publix, this home makes everyday living effortless. Situated in Holiday, you’ll enjoy quick access to shopping, dining, parks, and major roadways, with beautiful Gulf Coast beaches just a short drive away. Best of all, there are no HOA or CDD fees, giving you added flexibility and savings—making this an even more attractive option whether you're looking for a primary residence or a smart investment opportunity.

Listing is courtesy of: 27NORTH REALTY (813-645-4663)

Listing Agent: Linda Santa (856-220-3217)

Remarks: Location Location Location!!! Make this light flooded condo YOUR piece of paradise! Watch the mommy duck and her babies swimming on the lake as you sip your coffee by the back window... or walk to the pristine heated pool for your own swim. Later you can head down to one of several nearby beaches and watch a gorgeous sunset. Florida Living is all right there for you. Inside you will have everything you need too! A new A/C unit, inside laundry with newer washer and dryer, loads of closet space, and even your own personal shed for gear! So pack it up and come on down. Call today for an easy appointment!

Listing is courtesy of: COLDWELL BANKER REALTY (727-581-9411)

Listing Agent: Ann Marie Krzesinski (727-254-2568)

Remarks: Under contract-accepting backup offers. Tucked away in a quiet, peaceful neighborhood, this charming 2-bedroom, 2-bath home welcomes you with warmth, character, and comfort from the moment you arrive. With beautiful new curb appeal and a brand-new fence framing the property, this home instantly feels like your own private retreat and the best part? No HOA and not in a flood zone, offering both freedom and peace of mind. Perfectly located just minutes from Anclote River Park, Sunset Beach, Howard Park Beach, Grand Boulevard Park, Meadows Park & Dog Park, and Beacon Square Park, and only about 35 minutes to Clearwater Beach. With quick access to SR-54, you’ll enjoy both convenience and a relaxed Florida lifestyle. Step inside and you’ll find a cozy living space filled with personality, highlighted by stunning cedar wood accents that add warmth and charm. Tile flooring runs throughout the entire home, making it both stylish and easy to maintain perfect for everyday living. Outside is where this property truly shines. The backyard has been thoughtfully designed for relaxing and entertaining, featuring an enclosed lanai, fire pit, fruit trees, shed, and solar lighting that creates the perfect evening atmosphere. Whether you’re hosting friends or enjoying a quiet night under the stars, this space feels like home. Adding even more value is a fully functional tiny home in the backyard, complete with AC and a mini-fridge ideal as a guest suite, private office, creative studio, or even a rental opportunity. Major upgrades provide peace of mind for years to come, including: • New Roof, AC, and Water Heater (2023) • Solar Panels for energy savings • City Water & Well Water options for additional efficiency • Two security cameras for added safety This is more than just a house it’s a place to relax, entertain, and truly enjoy Florida living. Move-in ready with all the major updates done… all that’s missing is you.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Georgete Frey, Llc (813-469-8073)