Search Holiday FL Pool Homes

Holiday FL Pool Homes

Holiday FL Pool Homes

Tampa Bay Premier Realty has a wide selection of Holiday FL pool homes for sale, from luxurious estate homes with sprawling grounds and sparkling pools to cozy bungalows with wrap-around porches and charming backyard oasis. With our extensive list of properties you are sure to find the perfect home for your family’s needs. From high-end luxury homes to cozy cottages, there is something for everyone. Plus, our knowledgeable agents can help you find the perfect Holiday FL pool home for your lifestyle and budget. 

We understand how important it is for families to find a home that accommodates their needs and wishes. Let us show you why so many families keep coming back to us for their vacation and retirement needs. We will help you find the perfect Holiday FL pool home that checks all of your boxes. 

Come explore our selection of homes and find the perfect one for you! Whether you are looking for a luxury estate or a cozy cottage, Tampa Bay Premier Realty has something that fits your lifestyle. With years of experience and a wide selection of real estate, we’re the perfect place to start your search. 

Let us help you find the home of your dreams in Holiday FL! Contact us today for more information on our selection and why so many families keep coming back to us for their real estate needs. We look forward to helping you make the best decision for your family. Thank you for choosing Tampa Bay Premier Realty!  

View Holiday FL Pool Homes

$488,000
4 Beds 2 Baths Key Vista Ph 04 SubDv. 34691 Zip Code
Virtually Staged. WOW! Take a look at this 4 BEDROOM, 2 BATHROOM, 3 CAR GARAGE POOL HOME LOADED WITH UPDATES AND UPGRADES IN THE STUNNING KEY VISTA COMMUNITY ON A QUIET CUL DE SAC. The open kitchen has been remodeled. THE CABINETS AND COUNTER TOPS HAVE BEEN REPLACED, NEW REFRIGERATOR, AND A NEW DISHWASHER. The QUARTZ KITCHEN ISLAND IS EXCELLENT FOR ENTERTAINING AND USING AS A CASUAL SPACE FOR BAR STOOLS. The big open family says bring your sectional and huge TV because there is plenty of room! THE SLIDERS TO THE POOL HAVE RECENTLY BEEN REPLACED AS WELL AS NEW WINDOWS IN THE BACK OF THE HOUSE. It sure feels like Florida here with the PLANTATION SHUTTERS and light bright colors and SPARKLING SWIMMING POOL. There are no rear neighbors, you can enjoy your pool and outdoor space in private. New interior paint in many of the rooms. THE PRIMARY BEDROOM HAS MORE THAN ENOUGH ROOM FOR A KING SIZE BED AND THE PRIMARY BATHROOM FEATURES A STAND UP SHOWER AND SOAKING TUB. There is enough room to stretch out with double sinks too! Some other noteworthy things about this very special home are HIGH CEILINGS, a NEW ROOF IN 2023, NEW AC IS 2017 AND A NEW HOT WATER HEATER. You don't have to go far to enjoy the community amenities! There is a huge heated pool, clubhouse, playground, tennis and pickleball courts, fitness center, and more. Key Vista Nature Park is about a mile away, Sunset Beach and Fred Howard Park in Tarpon Springs are just a short drive away!

2811 Ravendale Lane, Holiday

$599,999
3 Beds 4 Baths Ibis Sub SubDv. 34691 Zip Code
"Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom-built executive residence, privately situated on a quiet cul-de-sac within an exclusive gated community. Offering 2,367 square feet of thoughtfully designed living space, this exceptional three-story home combines luxury, comfort, and functionality with partial Gulf views from multiple balconies. From the moment you arrive, the impressive stamped concrete driveway and striking architectural design create unforgettable curb appeal. Inside, you'll find soaring ceilings, custom 8-foot doors, elegant crown molding, engineered hardwood flooring, marble and travertine finishes, and an open-concept floor plan designed for both entertaining and everyday living. The gourmet kitchen is truly the heart of the home, featuring granite countertops, abundant custom cabinetry, a walk-in pantry, breakfast bar, and newer stainless-steel appliances—perfect for preparing meals while staying connected with family and guests. Escape to the luxurious owner's retreat occupying the entire upper level. This private sanctuary offers partial Gulf views, a spacious walk-in closet, and a spa-inspired ensuite featuring dual vanities, an oversized walk-in shower, and a relaxing whirlpool tub. Step outside and enjoy Florida living at its finest. Four travertine balconies provide multiple places to relax and enjoy the coastal breeze, while the beautiful in-ground pool and expansive paver patio create the perfect setting for entertaining family and friends. The oversized garage offers room for multiple vehicles, a workshop, abundant storage, and even includes a convenient full pool bath.Recent upgrades provide peace of mind and modern convenience, including: New roof (2021), Newer-zone HVAC system, Updated stainless-steel kitchen appliances Central vacuum system Premium flooring throughout. Ideally located enjoy indoor pickleball, weekly gymnasium schedule, summer camp, soccer fields, baseball, tennis and more at J. Ben Harrill Recreation Center is a short walk from your front gate. Just minutes from Anclote Gulf Park, public boat ramps, Gulf beaches, the Pinellas Trail, and the world-famous Tarpon Springs Sponge Docks, you'll also enjoy convenient access to shopping, dining, and endless waterfront recreation. Luxury, location, and lifestyle come together in one extraordinary home. Schedule your private showing today and discover why this exceptional property is one you won't want to miss.

3020 Sheppards Crook Court, Holiday

$549,000
4 Beds 3 Baths Baileys Bluff Estates SubDv. 34691 Zip Code
Perfectly designed for family living and entertaining, this house boasts an array of features that cater to every need. The primary bedroom is a true retreat, featuring a whirlpool tub, a stand-up shower, and a vanity that all contribute to a spa-like atmosphere. The room is generously sized with vaulted ceilings, creating an airy and open feel. Additionally, a bonus room with slider doors and bay window provides direct access to the pool deck, making it perfect for unwinding after a long day. The dining room is a charming space with a built-in buffet and French doors that lead out to the pool deck, enhancing the indoor-outdoor flow. The kitchen is a chef's delight, equipped with ample cabinetry, all stainless-steel appliances, and granite countertops. An eat-in counter extends into the living area, which is adorned with more slider doors opening to the pool deck, perfect for seamless entertaining. Comfortable Bedrooms and Private Spaces, in addition to the primary suite, the house includes another bedroom with two closets and a private bathroom, offering privacy and convenience. The final oversized bedroom is located at the far end of the house, featuring two large closets and more sliders that lead to the pool deck. This bedroom is accompanied by a bathroom with a stand-up shower and an oversized bathtub. The backyard is an entertainer's paradise, fully fenced with an inground pool that is lanai covered, set on an oversized pool deck. It provides the perfect setting for hosting friends and family or enjoying a quiet evening by the water. Additional Features are High elevation ensures no past flooding, providing peace of mind. 2-car garage with a brand-new garage door opener for convenience. This house is conveniently located just minutes away from the Bailys Bluff community BOAT RAMP with Gulf access, a Clubhouse with beautiful Gulf views with access to set sail your Kayak.

2210 Bayou Drive, Holiday

$380,000
2 Beds 2 Baths Shadow Oaks Sub SubDv. 34690 Zip Code
Poolside Living Meets Prime Location! This beautifully maintained pool home offers a desirable split-bedroom floor plan, giving the primary suite added privacy from the secondary bedrooms. Step inside to discover a gorgeous, updated kitchen remodeled in 2021, featuring modern finishes, electrical outlets conveniently installed within the cabinetry, and Alexa-controlled under-cabinet lighting for added style and functionality. The spacious primary suite provides a private retreat, while the open living areas flow seamlessly to the outdoor oasis. Enjoy Florida living year-round with a screened-in lanai, covered patio, and sparkling pool—perfect for entertaining guests or relaxing after a long day. This home has been thoughtfully updated with numerous improvements, including updated electrical, a brand-new garage door, epoxy-coated garage floors, and a water heater installed in March 2022. Roof 2012 Outside, you’ll find a storage shed for additional space and new fencing with double gates, offering convenient access for boats, trailers, or recreational vehicles. Ideally located just 10 minutes from downtown Tarpon Springs and 15 minutes from downtown New Port Richey, you’ll enjoy easy access to charming waterfront dining, shopping, festivals, and local entertainment. You’re also only minutes from Fred Howard Park and Beach, one of the area’s most beloved coastal destinations. Plus, Clearwater-St. Pete Airport and Tampa International Airport are both within approximately 45 minutes, making travel a breeze while keeping you close to all the area’s popular downtowns, restaurants, and local hotspots. Don’t miss this opportunity to own a move-in-ready pool home in an unbeatable location that combines comfort, convenience, and the best of Florida living.

3110 Shadow Oaks Drive, Holiday

$306,000
3 Beds 2 Baths Holiday Lake Estates 21 SubDv. 34691 Zip Code
9K PRICE REDUCTION!!! NO HOA!!! Welcome to your Holiday home retreat! Nestled against a conservation-lot along the canal, you'll enjoy peaceful nature views and abundant wildlife right from your backyard while enjoying the privacy of no rear neighbors, a true rarity at this price point. This beautifully maintained 3-bedroom, 2-bath, 1-car garage + extra wide driveway, screened lanai, and fully fenced home offers 1,462 square feet of comfortable Florida living. Inside, you'll find a bright, functional floor plan with a living room and dining area, a versatile family room or office space, and three generously sized bedrooms with two full baths. Step outside to your own secluded oasis featuring an inground pool enclosed by a screened lanai — ideal for year-round entertaining, weekend cookouts, or simply relaxing in the Florida sunshine in total comfort. Major-ticket items are already taken care of: new impact windows and sliding glass door installed in 2025. Roof, HVAC and pool pump 2016, plus a brand-new 2026 water heater - move in with confidence and skip the costly upgrades. Best of all - NO HOA and NO CDD fees! Access the Coastal Anclote Trail right from the neighborhood and bike to the Anclote River Boat Ramp and fishing pier or connect to the Pinellas Trail in Tarpon. Just a short drive to Fred Howard Park, white-sand beaches, and the scenic causeway. You're also minutes from historic Tarpon Springs Sponge Docks, fantastic Greek dining, shopping, golf, and all the charm the Nature Coast has to offer. Homes like this — with a pool, conservation lot, no HOA, — don't come along often. Schedule your private showing today before it's gone!

1853 Dartmouth Drive, Holiday

$1,265,000
3 Beds 3 Baths Baileys Bluff Estates SubDv. 34691 Zip Code
Discover the charm of Florida’s Gulf Coast in this beautifully crafted waterfront home, set along Rocky Creek within the private and sought-after Bailey’s Bluff neighborhood. Tucked away on a peaceful street, the property showcases wide-open water views, stunning sunsets, and easy access to the Gulf, making it an excellent choice for boating enthusiasts and those seeking a relaxed coastal lifestyle. A private dock equipped with a 12,000-pound boat lift allows for convenient days out on the water, while the home’s history of no flooding from past storms or hurricanes provides added reassurance. Designed with both comfort and entertaining in mind, the residence seamlessly blends indoor and outdoor spaces, featuring large screened-in area with a heated private in-ground saltwater pool and a fully fenced-in backyard—ideal for gatherings or unwinding in the coastal air. The primary suite serves as a serene escape, complete with dual walk-in closets, access to both front and back balconies, and a well-appointed bathroom featuring double vanities and a spacious walk-in shower. On the lower level, an air-conditioned space adds versatility and is currently utilized as a recreation and game area, along with laundry facilities, a pool bath, and extra storage, all connected to a split two-car garage. Recent updates include a new roof installed in April 2025. Residents also have the option to join the community HOA for $100 a year, granting access to a private beach, clubhouse, and boat ramp. Conveniently located near Key Vista Nature Park and the waterfront attractions of Tarpon Springs, this property presents a unique opportunity to enjoy upscale coastal living in a tranquil setting.

3114 Bluff Boulevard, Holiday

$1,859,900
4 Beds 4 Baths Baileys Bluff Estates SubDv. 34691 Zip Code
Stunning Ocean views from this waterfront paradise. The opportunity has arisen to acquire the former home of the renowned local artist Elaine Hahn and AIA emeritus architect Byron G McIntyre. Located in the sought-after Bailey’s Bluff community, this stunning 4-bedroom, 4-bath elevated home offers 3,412 square feet of coastal living with panoramic water views throughout and 160 feet of private water frontage with direct access to the Gulf. Located at the very end of a Cul-de-sac the private driveway leads to a spacious 4 plus vehicle garage. Take the inside elevator to the open plan 2nd floor, with feature light maple hardwood flooring accentuating the amazing natural light that flows into the living room. This floor also contains an open-plan kitchen, dining area, master bedroom suite and artist studio which has the most amazing views you will find for any home office. There is a covered front balcony and wrap around back balcony where you can enjoy the wonderful Gulf breezes. The third floor has three further bedrooms and addition Den/office. Also, you will find a secluded third-floor balcony that looks out at more spectacular views across to Anclote Key. In addition to the ground level garage, there is a covered parking area. Inside the garage is workshop space with French doors onto the pool deck. The backyard has a tranquil, tropical and beach feel with floating dock and boat lift. Take a 15-minute stroll to Key Vista Nature Park with its many trails and observation tower overlooking the Gulf. Enjoy boating, fishing, scalloping and island hopping. A short drive to a recreational complex, parks, beaches and the charming community of Tarpon Springs, complete with shopping and dining options. This home is solidly built to withstand hurricanes, being elevated, and with concertina or roll down shutters to all windows. During 2024 storms only suffered minor damage, not even losing power. There is no HOA, but an optional Baileys Bluff Civic Assoc. membership is just $100 a year, providing a private beach, boat ramp, & clubhouse. Don't miss the opportunity to make this slice of paradise your own!

1906 Gulfview Drive, Holiday

$825,000
3 Beds 3 Baths Baileys Bluff Estates SubDv. 34691 Zip Code
Virtually Staged. Open access to the Gulf!! Experience elevated waterfront living in this elegant 3 bed/2 bath residence with a versatile bonus room, thoughtfully designed to blend architectural charm, refined finishes, and seamless indoor–outdoor flow, all in the sought after Baileys Bluff Estates! The generously sized secondary bedrooms offer ample closet space and share a beautifully appointed full bath with a tub/shower combination. A hallway linen closet with built-in shelving provides additional storage. The primary suite is a true retreat, featuring sliding-door access to the lanai and a spa-inspired bath complete with a step-in shower with sliding glass doors—also opening to the exterior—dual-sink vanity, private water closet, and a dedicated dressing hallway with abundant closet space. A separate pool-access bath with sink and toilet can be closed off from the primary suite for added privacy. A nearby washer and dryer closet enhances everyday convenience. The main living areas impress with soaring volume ceilings, recessed lighting, and a striking corner stone fireplace anchoring the space. The chef’s kitchen is as functional as it is beautiful, showcasing wood soft-close cabinetry, granite countertops, stainless steel appliances, a breakfast bar, pantry closets with extensive shelving, a built-in corner desk, and a sun-filled breakfast nook. Architectural details add warmth and character, including a barn-style sliding door allowing the kitchen to be closed off when desired, and a decorative wicker-accent opening that enhances the home’s charm. A flexible dining area offers the option of formal dining and opens through sliding doors to a charming brick patio. The bonus room provides exceptional flexibility—ideal as a home office, media room, or optional fourth bedroom—complete with a utility sink closet, additional storage, and direct garage access. Outdoors, the expansive screened-in lanai and pool create a private oasis perfect for entertaining, complemented by an outdoor shower. The generous fenced backyard leads to your waterfront dock area, where tranquil water views can be enjoyed from the living room, breakfast nook, dining area, and kitchen. Additional highlights include light wood luxury vinyl flooring throughout; tile flooring in all bathrooms, oversized windows providing abundant natural light, ample storage throughout, and an oversized two-car garage. Located just two blocks from the Coastal Anclote Trail, which offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs. Enjoy easy water access via the bayou and creek with just a five-minute boat ride to the Gulf. The area is also ideal for kayaking. Pickleball courts with weekly league play are located within one mile. This exceptional waterfront property offers the perfect blend of lifestyle, comfort, and convenience. Schedule your private showing today.

2138 Bayou Drive, Holiday

$294,000
3 Beds 2 Baths Beacon Square SubDv. 34691 Zip Code
***FEMA FLOOD INSURANCE PAID THROUGH NOVEMBER 2027***FULLY TRANSFERABLE TO THE NEW OWNER. INSTANT VALUE AND SAVINGS. DON’T MISS THIS PROTECTED HOME OPPORTUNITY. This beautifully updated 3-bedroom, 2-bath home features a spacious, open layout perfect for everyday living and entertaining. Enjoy ceramic tile floors throughout, remodeled bathrooms, and a modern kitchen with granite countertops and stainless steel appliances. The primary bathroom features dual sinks and granite finishes, adding a touch of elegance. Step outside to your private backyard retreat with an in-ground pool, screened enclosure, side jacuzzi, and a cozy patio with BBQ—ideal for outdoor gatherings. The home features a new roof (2026), resistant hurricane windows, hurricane shutters, a pavered driveway, fresh paint, lush landscaping, and major updates, including an updated electrical panel (2016), a water heater (2015), a brand-new AC unit inside (2025), an AC unit outside (2019) and a pool liner replacement in December 2025 for added peace of mind. Additionally, the home includes a finished bonus room located at the rear of the house, fully enclosed and with flooring, offering flexible use as a personal gym, meditation or relaxation room, home office, or creative studio—customizable to suit your lifestyle needs. Conveniently located near Anclote Beach, parks, and US-19, just 15 minutes from Tarpon Springs and 35 minutes from Honeymoon Island. Restaurants, shopping, and everyday essentials are only five minutes away. Updated, comfortable, and perfectly located—this home is ready to enjoy the Florida lifestyle.

3625 Richboro Drive, Holiday

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