Holiday Homes with Pool

Holiday Homes with Pool

Welcome to Holiday, a charming city located in Pasco County, Florida. Known for its beautiful weather, friendly community, and abundance of recreational activities, Holiday is an ideal place to call home.

Situated in the sunny state of Florida, Holiday offers residents a year-round tropical climate, making it perfect for those who enjoy outdoor activities and spending time by the pool. Speaking of pools, if you're looking for homes with pool, you're in luck! Holiday boasts a wide range of properties that feature refreshing swimming pools, allowing you to relax and cool off right in your own backyard.

Whether you're a family looking for a spacious home with a pool for the kids to enjoy, or a couple seeking a tranquil oasis to unwind after a long day, Holiday has something to suit every lifestyle and budget. From cozy bungalows to modern villas, you'll find a diverse selection of homes with pool options in this area.

In addition to its poolside living, Holiday offers a variety of amenities and attractions for residents to enjoy. Explore the nearby Gulf of Mexico beaches, go fishing or boating on the Anclote River, or take a stroll through the local parks and nature reserves. With its close proximity to Tampa and Clearwater, you'll also have easy access to a wide range of shopping, dining, and entertainment options.

If you're ready to dive into the poolside living in Holiday, start exploring the available homes today. Don't miss out on the opportunity to make this vibrant city your new home.

Newest Holiday Homes with Pool

2 Beds ⋅ 2 Baths ⋅ Tahitian Gardens Condo SubDv. ⋅ 34691 Zip Code

Welcome to your bright and inviting 2-bedroom, 1.5-bath condo in Tahitian Gardens, a desirable 55+ gated community with a low monthly maintenance fee of $282.00 where Florida living is all about relaxing, connecting, and enjoying life. Filled with natural light and offering a comfortable, low-maintenance layout, this home is the perfect place to settle in and enjoy everything the Florida lifestyle has to offer. And the best part? You’re not just buying a home - you’re joining a community. Residents enjoy a heated community pool, clubhouse, shuffleboard and a wonderful calendar of social activities including cookouts, bingo, fashion shows, dances, line dancing, sailboat races, and more. Card and game enthusiasts can enjoy mahjong, dominoes, and other games while getting to know the neighbors. With low HOA fees and plenty to enjoy right outside your door, there’s more time to do the things you came to Florida for — relax by the pool, meet friends, stay active at the gym, or simply enjoy a slower, easier pace of life. Location is another major highlight. You’re just minutes from shopping, restaurants, parks, and the beautiful beaches of the Tarpon Springs area, with the famous Sponge Docks only about 10 minutes away. Tampa International Airport is approximately an hour away, making visits from family and friends - and your own travels - convenient. Not in the flood zone!

4359 Tahitian Gardens Circle Unit B, Holiday

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

Move-in ready and beautifully updated, this charming 2-bedroom, 2-bath home features an oversized one-car garage, a brand-new above-ground pool with ladder, and inviting indoor-outdoor living spaces. The bright, open floor plan is ideal for everyday living and entertaining, while the spacious, fully fenced backyard provides plenty of room to relax, gather, or enjoy time with pets. Recent improvements include a new A/C system, water heater, kitchen appliances, washer and dryer, lighting, screened front and rear patios, outdoor pool shower, and above-ground pool—all completed in 2026. The hallway bathroom was also refreshed in 2026 with new flooring, vanity, faucet, and lighting. Additional upgrades include fresh interior paint (2026), vinyl flooring (2025), new windows (2025), a privacy fence (2025), and a roof installed in 2019. With no HOA and no flood insurance currently required, this property offers added flexibility and value. Enjoy a convenient location approximately eight minutes from the famous Tarpon Springs Sponge Docks, 36 minutes from Clearwater Beach, and 37 minutes from Tampa International Airport, with shopping, dining, employment centers, and Tampa Bay destinations within easy reach. Everything has been thoughtfully prepared for its next owner—simply unpack, settle in, and start enjoying your new home.

3748 Redwood Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Tahitian Gardens Condo SubDv. ⋅ 34691 Zip Code

Tucked away in a quiet, secluded corner of the gated Tahitian Gardens community, this desirable end unit offers extra privacy and effortless, low-maintenance living! The bright, single-story layout features zero carpet with durable luxury vinyl and tile flooring throughout, plus a primary bedroom complete with a private half bath, a spacious walk-in closet and a large laundry/utility closet too! Sip your morning coffee on the cozy front porch or head out to enjoy the community's sparkling pool, active clubhouse, and walking paths. The affordable monthly fee covers exterior and grounds maintenance, security, and amenities for complete peace of mind. A prime location right off US-19 close to shopping, dining, and Gulf beaches—it's the perfect choice for a perfect retirement, easy winter retreat, or smart investment! MOVE IN READY !

4333 Tahitian Gardens Circle Unit A, Holiday

2 Beds ⋅ 2 Baths ⋅ Orangewood Village SubDv. ⋅ 34690 Zip Code

Welcome to 4640 Tropical Lane in Holiday! This 2-bedroom, 1.5-bath single-family home offers 988 square feet of living space with a flexible floor plan and plenty of potential. Features include a spacious living area, Florida room, attached one-car garage, fenced backyard and private in-ground pool. The additional flex space provides options for a home office, guest space or hobby room. Conveniently located near shopping, dining and major roadways. This property is ready for a new owner to bring their personal touches and make it their own. Property is being sold as-is. Schedule your showing today!

4640 Tropical Lane, Holiday

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

Welcome to your tropical oasis and the waterfront lifestyle most people only dream about! This beautifully renovated 3-bedroom, 3-bathroom waterfront pool home with a bonus room is situated on a large lot along the Anclote River, featuring approximately 70 feet of seawall with direct Gulf access. Powered by solar, this stunning home offers a desirable split-bedroom floor plan and new wood-plank tile flooring throughout. As you enter, you'll immediately appreciate the spacious living area, which flows seamlessly into the dining room. Sliding glass doors open to an expansive screened-in patio, creating the perfect indoor-outdoor living experience. To the left, a hallway leads to two generously sized guest bedrooms. One features its own private bathroom with access to the pool area, while the second guest bedroom offers a large walk-in closet and is conveniently serviced by the additional guest bath. The beautifully appointed kitchen features stainless-steel appliances, wood cabinetry, granite countertops, and a cozy breakfast nook. The spacious primary suite offers a walk-in closet and an updated bathroom with a convenient step-in shower. Just off the primary suite, a large bonus room provides flexible space for a home office, den, nursery, or additional living area. Step outside and discover your own private Florida retreat. The expansive screened-in patio overlooks a beautiful swimming pool surrounded by stamped concrete, while the large, fenced backyard provides plenty of room to relax and entertain. A composite deck with pergola creates an inviting space for outdoor dining, lounging, and enjoying the Florida sunshine year-round. For the boating enthusiast, this property truly shines. Just steps from the deck is a composite boat dock with a 10,000-lb boat lift, offering direct access to the Gulf. Whether you're heading out for a day on the water, exploring nearby tropical islands, or enjoying the area's beautiful sandy beaches, this waterfront home makes it easy to embrace the Florida lifestyle. Bring your boat, your family, and your love of the water—this is Gulf Coast living at its best!

1324 Chancellor Drive, Holiday

1 Beds ⋅ 1 Baths ⋅ Tahitian Gardens Condo SubDv. ⋅ 34691 Zip Code

Welcome to easy Florida living in the active 55+ community of Tahitian Gardens! This charming 1-bedroom, 1-bathroom villa-style condo offers comfortable, low-maintenance living in a community where there is always something to do. Fresh interior paint and luxury vinyl flooring create a clean feel, while a newer water heater (2022) helps make this home truly move-in ready. Residents of Tahitian Gardens can take advantage of the community pool and a variety of activities and social events, including cookouts, fashion shows, bingo, shuffleboard, bocce ball, horseshoes, sailboat races, dances and line dancing. Game enthusiasts can enjoy pinochle, euchre, mahjong, dominoes and other card games. Located only 10 minutes from Tarpon Springs and sponge docks, this community is close to restaurants, shopping and activities. Whether you're looking for a full-time Florida home, a seasonal getaway, or a place to enjoy an active and social lifestyle, this villa offers an inviting opportunity to make Florida living simple.

4349 Tahitian Gardens Circle Unit G, Holiday

3 Beds ⋅ 2 Baths ⋅ Oak Hill SubDv. ⋅ 34690 Zip Code

This 3-bedroom, 2-bathroom home is located in the Oak Hill Unit neighbourhood. This home features a welcoming open floor plan that creates a seamless flow throughout the main living spaces, perfect for both everyday life and entertaining. The updated kitchen is beautifully appointed with granite countertops and stainless-steel appliances. For your privacy, the primary bedroom includes a dedicated attached bathroom. Step outside to discover your own private swimming pool, offering a great space to relax and unwind. Conveniently located near public schools and just a short drive to Gulf beaches, shopping, dining, and other amenities. Schedule your private showing today!

2641 Flintwood Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Key Vista Ph 04 SubDv. ⋅ 34691 Zip Code

Welcome to this beautifully updated three-bedroom, two-bathroom pool home in the gated community of Key Vista in Holiday! Offering an impressive combination of thoughtful updates, smart-home technology, and resort-style amenities, this home is designed for comfortable and easy Florida living. Major improvements include a 2024 roof with a 25-year warranty, 2024 water heater, 2019 windows, 2021 Shaw Luxury Vinyl Plank flooring with 5¼-inch baseboards, and a 2020 AC compressor replacement featuring a 3-ton, 14 SEER heat pump with a 10-year warranty. The AC condenser is also from 2020. Additional updates include 2019 kitchen appliances, 2021 garage door opener and springs, 2017 washer and dryer, 2021 renovations to both bathrooms, and permanent exterior lighting installed in 2025. The open-concept interior offers a spacious and inviting layout with a large kitchen island perfect for meal preparation and casual dining, granite countertops, stainless steel appliances, abundant cabinetry, and a breakfast nook overlooking the pool. A separate dining room provides additional space for entertaining. The spacious primary bedroom features a vaulted ceiling, ceiling fan, and relaxing pool views. The beautifully renovated primary bathroom features a dual-sink granite-top vanity, glass-enclosed shower, and newly tiled finishes, while the second bathroom was also renovated in 2021. Step outside and enjoy your private pool and fenced backyard, designed for effortless outdoor living. The pool features Hayward OmniLogic automation that allows you to control the pump, spa, and heater remotely from your smartphone, making it easy to turn everything on before you even step outside. The pool and spa lights can also be operated remotely, eliminating the need to go outside the screened enclosure to adjust switches. A 2025 salt cell replacement provides added convenience, while 2026 LED pool and spa lights offer enhanced lighting and remote operation. The pool also features beautiful natural travertine decking, a built-in pool-wall vacuum system, and an included Hayward robotic pool cleaner. The extended screened lanai features an Elite roof, creating additional covered outdoor living space. Smart technology continues throughout the home with a Sensi smart thermostat that can be controlled through your smartphone and a smart garage door opener that can notify you if the garage is left open too long or when you leave home. A whole-home generator provides added peace of mind, and the home is prewired for the generator with a transfer switch installed around 2023. Additional exterior features include gutters, a professionally installed drainage system, hurricane shutters for the entire home, front-door and Palladian-window mesh hurricane protection, and a professionally painted exterior using Sherwin-Williams Emerald Shield paint in 2021. Ring Doorbell and Ring security cameras provide additional smart-home convenience and security around the front garage area and pool lanai. The Key Vista community offers an outstanding lifestyle with a community pool, clubhouse, sport courts, and additional amenities, while the master association includes cable. Conveniently located near the J. Ben Harrill Recreation Complex, numerous parks and trails, dining and shopping options, and zoned schools. Schedule your showing today!

2530 Arrowpointe Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv. ⋅ 34691 Zip Code

Welcome to effortless Florida living in this meticulously maintained 3-bedroom, 2-bath, single-story villa, offering approximately 1,740 square feet of spacious, maintenance free living with the comfort and feel of a single-family home. Situated on a premium pond-view lot in the desirable Gulfwinds community, this inviting residence combines thoughtful upgrades, stylish finishes, and a carefree Florida lifestyle. From the moment you enter, the open-concept kitchen, dining, and family room create a warm and welcoming space designed for both everyday living and entertaining. The well-appointed kitchen features 42-inch nutmeg hardwood cabinetry, Caledonia granite countertops, an undermount double sink, modern appliances, glass-top range, microwave/exhaust hood, dishwasher, and a convenient closet pantry. Beautiful 18-inch ceramic tile extends through the wet areas and hallways, while crown molding, pendant lighting, and recessed lighting add a sophisticated finishing touch. The main living area features hand-scraped engineered hardwood flooring and a contemporary industrial-style ceiling fan. Sliding glass doors open to an extended screened lanai and oversized paver patio, creating an exceptional outdoor living space overlooking the peaceful pond—a perfect setting for morning coffee, evening gatherings, or simply enjoying the beautiful Florida surroundings. The spacious primary suite continues the engineered hardwood flooring and offers a generous walk-in closet and an ensuite bath with dual vanities, a relaxing garden tub, and a separate step-in shower. Two additional bedrooms provide excellent flexibility for family, guests, hobbies, or a home office. One bedroom is currently configured as a craft room, with cabinetry that can remain or be removed to suit the new owner's needs. Energy efficiency and peace of mind are also priorities here, with double-pane insulated windows, R-38 attic insulation, and advanced air-sealing techniques. The HVAC SYSTEM WAS REPLACED IN 2022, and the home carries an ENERGY STAR rating. Additional benefits include no CDD fees and a location that is not in a Special Flood Hazard Area. Gulfwinds offers the ultimate in low-maintenance living. Residents enjoy a heated community pool and beautifully maintained grounds, while the HOA takes care of many of the major exterior responsibilities, including lawn and shrub care, roof repair and replacement, exterior painting, high-speed internet, and cable service, including Hulu, Disney+, and ESPN. It's an ideal lock-and-leave lifestyle for seasonal residents, frequent travelers, or anyone who simply wants to spend less time on home maintenance and more time enjoying Florida. Conveniently located near marinas, parks, golf, shopping, and dining, this home is just minutes from the Gulf of Mexico and the world-famous Tarpon Springs Sponge Docks. Enjoy the tranquility of a beautifully maintained community while remaining close to the very best of the Florida lifestyle.

2219 Parrot Fish Dr, Holiday

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv. ⋅ 34691 Zip Code

Virtually Staged. Beautiful Corner unit in Holiday Lake Villas Condos. This beauty is located directly across from the Club House and Pool. There are 2 bedrooms and 2 bathrooms. The primary bedroom features sliding glass doors directly to the enclosed porch, a walk in closet, a mirrored dressing table as well as a dual sink vanity. The kitchen has a breakfast nook and a pass through to the living room, dining room. Unit has been beautifully updated with fresh paint, flooring and appliances. This condo was built in 1981 and has 1318 sq ft living area plus a 216 sq ft enclosed porch. Just perfect for a maintenance free winter home or a fulltime residence

3936 Sailmaker Lane, Holiday

5 Beds ⋅ 6 Baths ⋅ Forest Hills Un #22 SubDv. ⋅ 34690 Zip Code

GREAT PRICE REDUCTION * HURRY BEFORE IT'S GONE * WHERE CAN YOU GET A 1.2 ACRE PIECE OF WATERFRONT PROPERTY WITH 5 BEDROOMS, 4 .5 BATHS AND UNOBSTRUCTED WATER VIEWS * HERE'S ANOTHER OPPORTUNITY TO PURCHASE THIS UNIQUE AND MAGNIFICENT WATERFRONT HOME, SURROUNDED ON THREE SIDES BY SPECTACULAR WATER VIEWS * THIS HOME WITH SPANISH AND MEDITTERANEAN ARCHITECTURE, WITH FEATURES SUCH AS BEAMED CEILINGS AND ARCHED OPENINGS THROUGHOUT IS VERY SPACIOUS AND HAS AN ATTRACTIVE LAYOUT ON TWO FLOORS * TWO MASTER BEDROOMS, EACH ACCESSED BY TWO SEPARATE STAIRWAYS OPEN UP TO DECKS WITH UNOBSTRUCTED WATER VIEWS * BEAUTIFUL MARBLED DESIGN CERAMIC TILE THROUGHOUT HOME * THE GROUND FLOOR IS ACCESSED BY A WELCOMING FOYER WITH STEP DOWN TO A LARGE LIVING ROOM ON ONE SIDE AND OFFICE/TV ROOM ON THE OTHER * HALLWAY LEADS TO A LARGE LIBRARY, A HALF BATH AND A STAIRWAY TO THE SECOND FLOOR * FOUR BEDROOMS AND 3 FULL BATHS GREET YOU WITH SERENE AND PEACEFUL VIEWS OF THE ANCLOTE RIVER * UPGRADES BY THE PRESENT OWNERS INCLUDE THREE AC SYSTEMS REPLACED WITHIN THE LAST 4 YREARS * 1 YR OLD HOT WATER HEATER * NEW KITCHEN WITH AMPLE CABINETS, ISLAND WITH SITTING AREA AND A SPACIOUS DINING AREA LEADING OUT TO THE POOL * THE GROUND FLOOR ALSO PROVIDES A MASSIVE GAMES ROOM WITH A WOOD BURNING FIREPLACE * PERFECT FOR GATHERINGS AND ENTERTAINTMENT * A FULL BATH WITH A SAUNA ADDS TO THE COMFORT OF THIS HOME * WALK OUTSIDE TO THE COVERED DECK FOR YEAR ROUND USE, HUGE PAVED DECK, POOL GAZEBO AND WATER VIEWS ALL AROUND. WITH 630 FEET OF WATERFRONT WALL PROVIDES NEW OWNERS THE OPPORTUNITY TO BUILD A DOCK WITH A BOAT LIFT AND POSSIBLY A BOATHOUSE * THE LARGE PIECE OF PROPERTY IS PERFECT FOR LOTS OF OUTDOOR ACTIVITIES * LOTS OF PARKING SPACE FOR MULTIPLE BIG TOYS AND VEHICLES * 3 LARGE OPEN GARAGE SPACES * DON'T MISS THIS ONCE IN A LIFETIME OPPORTUNITY TO OWN A BEAUTIFUL PIECE OF PARADISE * PRIVATE FINANCING WITH VERY GOOD TERMS AVAILABLE * Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Glenwood Gulf Trace SubDv. ⋅ 34691 Zip Code

Per recent Appraisal square footage is living space of 2151! Beautifully Updated 3-Bedroom Home on an Oversized Cul-de-Sac Lot Welcome home! This beautifully maintained 3-bedroom, 2-bath home sits on an oversized corner lot in a desirable cul-de-sac, offering extra space, privacy, and flexibility. With an impressive list of updates already completed, this home is truly move-in ready! 2019 — Exceptional Kitchen, Pool & Window Upgrades • Double-Pane, Impact-Rated Windows Installed, providing enhanced protection, energy efficiency, comfort, and peace of mind while also enhancing curb appeal and comfort. • Pool refinished and filtration system replaced. • Granite countertops add beauty, durability, and elegance. • Stainless steel appliances create a modern kitchen. • Soft-close kitchen cabinet drawers provide a premium finishing touch. 2020 — Added Protection • Gutters installed, helping direct rainwater away from the home. Well-fed irrigation system helps keep the lawn and landscaping looking green, healthy, and beautiful while providing an economical irrigation source. 2023 — Major System Improvements • Roof replaced, providing valuable peace of mind. • HVAC system replaced, keeping the home comfortable year-round. 2024 — Fresh Exterior • Exterior painted, delivering a fresh, attractive appearance and enhanced curb appeal. 2025 — Garage Upgrade • Garage door replaced, adding functionality, security, and curb appeal. NEW — Beautiful Flooring Luxury Vinyl Plank flooring has been newly installed throughout the main living spaces, creating a stylish, durable, and easy-to-maintain foundation. The Secondary bedrooms feature comfortable carpeting, creating cozy private spaces. Flexible Space to Make Your Own The home's 3-bedroom, 2-bath layout also offers additional space that can be transformed into an office, craft room, hobby space, or potentially a 4th bedroom, depending on your needs and applicable requirements. THE BIG STORY This home offers the rare opportunity to enjoy the benefits of years of thoughtful improvements without taking on the projects yourself. Major updates include the roof, HVAC, windows, pool, filtration system, gutters, exterior paint, garage door, kitchen features, irrigation system, and NEW flooring. Add the oversized cul-de-sac lot, private pool, flexible living space, and move-in-ready condition, and this home delivers an incredible combination of comfort, style, functionality, and value! Come see it, and make it yours!

3225 Hearthstone Court, Holiday

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