Holiday, FL Homes

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  $143,500

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft

  4345 Tahitian Gardens Cir Unit C, Holiday, FL 34691

  JUST REDUCED! This two-bedroom, BATH & HALF condominium located at the back of a cul-de-sac in Tahitian Gardens, a beautifully maintained GATED 55+ community can now be yours. Partially furnished and ready to move in. Features include oversized living room windows that provide natural lighting. The master bedroom contains a private half bath and walk-in closet. Enjoy your morning coffee or tea on

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 605-4447

  4345 Tahitian Gardens Cir Unit C, Holiday, FL 34691
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  /20

  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,522 Sq Ft
  • House for Rent

  5653 Andrea Dr, Holiday, FL 34690

  Property Id: 1830133HOME WILL BE AVAILABLE TO SHOW AFTER MARCH 3rd. This house features 3 bedrooms, 2 bathrooms, granite kitchen countertops, over 1,500 square feet of living space, and a single car garage. This house is renting for $1,900 per month with a $1,900 deposit for a total move of $3,800. We are seeking applicants who are able to provide income documentation for 2.5 times

  5653 Andrea Dr, Holiday, FL 34690
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  $225,000 Sold Nov 25, 2025

  4841 Aegean Ave, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Below List Price
  • $223/SF
  • 9 Days On Market

  Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES

  4841 Aegean Ave, Holiday, FL 34690
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  /2

  Est $637,749 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,654 Sq Ft

  1426 Flotilla Dr, Holiday, FL 34690

  1426 Flotilla Dr, Holiday, FL 34690
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  /36

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,102 Sq Ft

  1408 Jennings Dr, Holiday, FL 34690

  Beautifully RENOVATED 3-bedroom, 2-bath home located in Flood Zone X (no flood insurance required). Move-in ready with modern finishes and essential upgrades. Interior updates include new bathroom fixtures, granite countertops, kitchen appliances, new flooring throughout, fresh interior/exterior paint, new blinds, and dimmable lighting. Exterior enhancements include new front and back pagodas,

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 361-9268

  1408 Jennings Dr, Holiday, FL 34690
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  /20

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 1,114 Sq Ft
  • Condo for Rent

  1406 Bowsprit Ln Unit 1033, Holiday, FL 34691

  LOCATION, LOCATION, MINUTES AWAY FROM TARPON SPRINGS SPONGE DOCKS. A WELL KEPT 55+ COMMUNITY NOT IN A FLOOD ZONE. SWIMMING POOL AVAILABLE.. INSIDE LAUNDRY AND WATER SOFTENER. CABLE AND INTERNET, WATER & SEWER ALL INCLUDED, JUST PAY YOUR ELECTRICITY AND PUT SALT IN THE WATER SOFTNER. CONDO HAS BEEN UPDATED AND WELL CARED FOR. WASHER, DRYER, MICROWAVE, DISH WASHER, REFRIGERATOR. WORTH A LOOK. OH

  Charles Carter CHARLES P CARTER

  1406 Bowsprit Ln Unit 1033, Holiday, FL 34691
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  /2

  $415,000 Sold Jun 02, 2025

  2510 Big Pine Dr, Holiday, FL 34691

  • 4 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $205/SF
  • 147 Days On Market

  Current Estimated Value $423,077

  Last Listing Agent Ron Mastrodonato SANDPEAK REALTY

  2510 Big Pine Dr, Holiday, FL 34691
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  /2

  Est $198,029 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 972 Sq Ft

  2120 Calusa Trail, Holiday, FL 34690

  2120 Calusa Trail, Holiday, FL 34690
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  /23

  $235,000

  • 2 Beds
  • 1.5 Baths
  • 1,108 Sq Ft

  5412 Golden Nugget Dr, Holiday, FL 34690

  Beautiful 2-bedroom, 1.5-bathroom home in the heart of Holiday, featuring new windows, a large fenced yard, a screened patio, and fresh remodeling throughout, all in a fantastic location close to beaches, restaurants, and shopping. You must see this one before it’s gone! For full transparency, the home had a settlement investigation in 2007. Still, there have been no issues since, and it will be

  

  Anita McCracken P.A.

  F I GREY & SON RESIDENTIAL

  (727) 261-2398

  5412 Golden Nugget Dr, Holiday, FL 34690
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  /20

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • House for Rent

  2127 Erin Dr, Holiday, FL 34690

  Discover comfort in this well-appointed single-family home. Offering 2 bedrooms and 2 bathrooms, it’s designed for modern living.- Electric range, dishwasher, microwave, and refrigerator- Hookups for convenient laundry- Attached garage for secure parking- Central cooling and forced air heating- Ceiling fans installed for added comfort- Fenced yard for outdoor

  2127 Erin Dr, Holiday, FL 34690
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  /2

  $104,000 Sold Jan 14, 2026

  3136 Buckner Ct, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 768 Sq Ft
  • Built 1978

  Last Sold Summary

  • 10% Below List Price
  • $135/SF
  • 254 Days On Market

  Last Listing Agent John Grey FI GREY & SON INC COMMERCIAL

  3136 Buckner Ct, Holiday, FL 34690
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  /2

  Est $214,027 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 956 Sq Ft

  2527 Chancery Dr, Holiday, FL 34690

  2527 Chancery Dr, Holiday, FL 34690
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  $175,000

  • 2 Beds
  • 1.5 Baths
  • 842 Sq Ft

  4352 Tahitian Gardens Cir Unit M, Holiday, FL 34691

  Come see this IMMACULATE, WATERFRONT, 2-bedroom, bath and a half townhouse in the GATED 55+ community of Tahitian Gardens. This updated townhouse has gorgeous WATER VIEWS and the largest floorplan in the community. Freshly painted with numerous updates! App controlled smart lighting, HVAC and even a smart bath vent with Bose Wi-Fi speakers. The spacious living and dining area feature an abundance

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 496-6674

  4352 Tahitian Gardens Cir Unit M, Holiday, FL 34691
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  /6

  $2,100 per month

  • 4 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • House for Rent

  3440 Brookfield Dr, Holiday, FL 34691

  Escape to the charm of Holiday in this stunning 4 bedroom, 2 bathroom remodeled home. This beautifully updated home boasts a neutral color palate, new flooring, new paint, newer windows, setting the tone for a relaxing atmosphere. The heart of the home is the UPGRADED kitchen, featuring gorgeous granite countertops and stainless steel appliances. Spacious Primary Bedroom with an updated and

  Michele Strong ENGEL & VOLKERS BELLEAIR

  3440 Brookfield Dr, Holiday, FL 34691
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  /2

  $220,000 Sold Feb 18, 2025

  3236 Honeymoon Ln, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1973

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 24 Days On Market

  Current Estimated Value $231,342

  Last Listing Agent Madalina Tat NHR BROKERAGE LLC

  3236 Honeymoon Ln, Holiday, FL 34691
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  /2

  Est $328,866 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,656 Sq Ft

  3248 Darlington Rd, Holiday, FL 34691

  3248 Darlington Rd, Holiday, FL 34691
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  /31

  $149,900

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  4312 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  Experience the tranquility of condominium living with serene water views at your doorstep. This turnkey two-bedroom condo is located in Tahitian Gardens, a fully gated, active 55+ community. This corner unit is offered fully furnished and boasts significant upgrades including an open floor plan with tile flooring throughout. Large floor to ceiling living room windows. An updated bathroom which

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 761-4257

  4312 Tahitian Gardens Cir Unit E, Holiday, FL 34691
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  /16

  $1,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,634 Sq Ft
  • House for Rent

  5148 Forum Blvd, Holiday, FL 34690

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2164.90. That covers your base rent, $1995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5148 Forum Blvd, Holiday, FL 34690
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  $14,900 Sold Sep 08, 2025

  4699 Continental Dr Unit 144, Holiday, FL 34690

  • 1 Bed
  • 1 Bath
  • Built 1981

  Last Sold Summary

  • 17% Below List Price
  • 109 Days On Market

  Last Listing Agent Lane Parks Gulf Breeze Mobile Home Sales, LLC

  4699 Continental Dr Unit 144, Holiday, FL 34690
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  /2

  Est $178,775 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 956 Sq Ft

  2532 Sweetwood Dr, Holiday, FL 34690

  2532 Sweetwood Dr, Holiday, FL 34690
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  /28

  $299,000 Open Sun 1:30PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,334 Sq Ft

  3228 Rock Valley Dr, Holiday, FL 34691

  Welcome to this charming two bedroom, two bath home with a spacious Florida room that offers beautiful water views. The semi-open floor plan features updated kitchen counters, and fresh paint, along with new flooring installed after last year’s storms. Enjoy the serene water view complemented by a mature tree in the backyard, perfect for fishing and budget friendly lifestyle. The home has been

  

  Guillermina Rickey

  ENGEL & VOLKERS BELLEAIR

  (727) 761-7551

  3228 Rock Valley Dr, Holiday, FL 34691
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  /17

  $1,600 per month

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • House for Rent

  1415 Wickham Ln, Holiday, FL 34691

  Welcome to this freshly updated 3 bedroom, 1 bathroom home located in desirable Holiday Lake Estates, just minutes from Pinellas County. This home has been freshly painted inside and out and features no carpet throughout for easy maintenance.Recent upgrades include an updated kitchen with stainless steel appliances, an updated bathroom, and central A/C. New windows are being installed

  Brande Greenlee Kennedy GREENLEE REALTY GROUP

  1415 Wickham Ln, Holiday, FL 34691
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  /2

  $320,000 Sold Oct 17, 2025

  2648 Grand Blvd, Holiday, FL 34690

  • Land
  • 5.13 Acres
  • $62,378 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 96 Days On Market

  Current Estimated Value $533,415

  Last Listing Agent Robert Moore INTERNATIONAL TOP AGENTS REALTY

  2648 Grand Blvd, Holiday, FL 34690
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  /2

  Est $204,254 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  4233 Ridgefield Ave, Holiday, FL 34691

  4233 Ridgefield Ave, Holiday, FL 34691
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  /29

  $452,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  5253 Boardwalk St, Holiday, FL 34690

  Under contract-accepting backup offers. TRUE FLORIDA LIVING AT ITS BEST! Welcome to your waterfront oasis at 5253 Boardwalk Street in Holiday, Florida—where luxury meets lifestyle with direct Gulf access right from your backyard. This stunning 3-bedroom, 2.5-bathroom home has been completely rebuilt and reimagined with high-end finishes and thoughtful design throughout. From the moment you enter,

  

  Gigi Gauthier

  TRUE REALTY GROUP

  (727) 910-5580

  5253 Boardwalk St, Holiday, FL 34690
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  /16

  $1,965 per month

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft
  • House for Rent

  4048 Sunray Dr, Holiday, FL 34691

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2109.90. That covers your base rent, $1965.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  4048 Sunray Dr, Holiday, FL 34691
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  /2

  $450,000 Sold Jul 03, 2025

  2924 Windridge Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 2,069 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $217/SF
  • 32 Days On Market

  Current Estimated Value $455,711

  Last Listing Agent Cortney Bain CHARLES RUTENBERG REALTY INC

  2924 Windridge Dr, Holiday, FL 34691
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  /2

  Est $301,438 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  3419 Winder Dr, Holiday, FL 34691

  3419 Winder Dr, Holiday, FL 34691
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  /30

  $124,900 Pending

  • 2 Beds
  • 1.5 Baths
  • 768 Sq Ft

  4329 Tahitian Gardens Cir Unit B, Holiday, FL 34691

  Under contract-accepting backup offers. Welcome to this move-in ready two-bedroom, one and a half-bath condo in the desirable 55+ gated community of Tahitian Gardens. The open-concept layout offers a bright, inviting atmosphere, with a spacious primary bedroom with a large closet. Recent updates include laminate flooring throughout and fresh paint on all interior walls and doors. Enjoy the

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 291-9645

  4329 Tahitian Gardens Cir Unit B, Holiday, FL 34691
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  /16

  $1,800 per month

  • 3 Beds
  • 1 Bath
  • 1,433 Sq Ft
  • House for Rent

  1434 Weyford Ln, Holiday, FL 34691

  This pet-friendly home features modern finishes and a functional layout with ample kitchen storage, spacious living areas, and abundant natural light throughout. The private yard offers space suitable for gardening or outdoor relaxation. Conveniently located near schools, parks, dining, and local amenities. Technology-enabled maintenance services provide added convenience, and self-touring is

  Daniel Reyes MAIN STREET RENEWAL LLC

  1434 Weyford Ln, Holiday, FL 34691
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  /2

  $239,000 Sold May 30, 2025

  2532 Fentress Place, Holiday, FL 34691

  • 2 Beds
  • 2 Baths
  • 1,231 Sq Ft
  • Built 1971

  Last Sold Summary

  • $194/SF
  • 2 Days On Market

  Current Estimated Value $240,302

  Last Listing Agent Julie Barnhardt BHHS FLORIDA PROPERTIES GROUP

  2532 Fentress Place, Holiday, FL 34691
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  /2

  Est $221,579 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,077 Sq Ft

  3538 Bigelow Dr, Holiday, FL 34691

  3538 Bigelow Dr, Holiday, FL 34691
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  /28

  $179,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  3518 Emory Dr, Holiday, FL 34691

  Charming Holiday home full of potential and solid bones — perfect as a starter home, renovation project, or investment opportunity. This 2 bedroom, 1 bathroom home features a 1 car garage with an extended driveway plus an enclosed Florida room bonus space ideal for a home office, playroom, or extra living area. Major updates provide peace of mind including ROOF 2018, WATER HEATER 2019, HVAC 2017,

  

  Andzelika Duraj

  FUTURE HOME REALTY INC

  (727) 855-3218

  3518 Emory Dr, Holiday, FL 34691
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  /15

  $1,605 per month

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • House for Rent

  3530 Brompton Dr, Holiday, FL 34691

  Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

  3530 Brompton Dr, Holiday, FL 34691
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  $223,000 Sold May 14, 2025

  1446 Normandy Blvd, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • Built 1970

  Last Sold Summary

  • 5% Below List Price
  • $228/SF
  • 1 Day On Market

  Current Estimated Value $223,848

  Last Listing Agent Zerah Cruz LPT REALTY, LLC

  1446 Normandy Blvd, Holiday, FL 34691
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  /2

  Est $214,509 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 936 Sq Ft

  3818 Darlington Rd, Holiday, FL 34691

  3818 Darlington Rd, Holiday, FL 34691
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  /53

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  3238 Coldwell Dr, Holiday, FL 34691

  Price Reduction—Your Florida Dream Starts Here!Welcome home to this beautifully updated 3-bedroom, 2-bath retreat in the heart of Holiday, Florida, where modern style meets easy coastal living. Completely move-in ready, this home invites you in with a bright, open layout, fresh paint, and sleek luxury vinyl plank flooring that sets the tone for comfort and effortless entertaining.The

  

  Rick Bishop

  LPT REALTY, LLC

  (727) 624-1893

  3238 Coldwell Dr, Holiday, FL 34691
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  /15

  $1,475 per month

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • House for Rent

  3227 Darlington Rd, Holiday, FL 34691

  This 3-bedroom, 2-bath single-family home offers a spacious layout perfect for comfortable living. Enjoy a bright, open living area that flows easily into the kitchen and dining spaces ideal for entertaining or relaxing. The home features a fully fenced backyard. Pet friendly! Located close to shopping, dining, and local parks, youll love the easy access to U.S. 19 and nearby Gulf beaches.

  Kirby Dulin BHHS FLORIDA PROPERTIES GROUP

  3227 Darlington Rd, Holiday, FL 34691
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  /2

  $280,000 Sold Sep 11, 2025

  Unlisted Address

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1970

  Last Sold Summary

  • $220/SF
  • 11 Days On Market

  Current Estimated Value $282,534

  Last Listing Agent Michael Constantine RE/MAX ALLIANCE GROUP

  Unlisted Address
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  /2

  Est $239,008 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft

  4969 Lemonwood Loop, Holiday, FL 34690

  4969 Lemonwood Loop, Holiday, FL 34690

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