Holiday, FL Homes

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  $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
• Explore Holiday

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  /16

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  4358 Tahitian Gardens Cir Unit H, Holiday, FL 34691

  JUST IN TIME FOR WINTER! This beautiful 1-bedroom lake view condo can be yours. Located in Tahitian Gardens, a beautifully maintained 55+ gated community. This open floor plan corner unit features tile and luxury vinyl flooring, granite counters in the kitchen and bath, stainless-steel range and microwave. Tahitian Gardens has many activities including shuffleboard, arts and crafts, a bicycling

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 624-1776

  4358 Tahitian Gardens Cir Unit H, Holiday, FL 34691
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  $110,000 Sold Dec 02, 2025

  4328 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1973

  Last Sold Summary

  • $143/SF
  • 5 Days On Market

  Last Listing Agent Christina Probeyahn COASTAL PROPERTIES GROUP INTERNATIONAL

  4328 Tahitian Gardens Cir Unit E, Holiday, FL 34691
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  3303 Hampshire Dr, Holiday, FL 34690

  3303 Hampshire Dr, Holiday, FL 34690
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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

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • House for Rent

  3741 Kingsbury Dr, Holiday, FL 34691

  Welcome to this charming single-family home nestled in the desirable Beacon Square community. This delightful property features 2 bedrooms, 2 bathrooms, and a 1-car garage, offering comfortable living spaces for you and your family. As you step inside, you're greeted by a cozy family room adorned with a lovely fireplace, perfect for relaxing evenings with loved ones. The spacious bedrooms provide

  

  Antje Anderson

  COASTAL PROPERTIES GROUP INTERNATIONAL

  (727) 606-8030

  3741 Kingsbury Dr, Holiday, FL 34691
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  /2

  $224,000 Sold Jan 16, 2026

  2721 Flint Isle Place, Holiday, FL 34691

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Above List Price
  • $206/SF
  • 17 Days On Market

  Last Listing Agent Cory Byrd F I GREY & SON RESIDENTIAL

  2721 Flint Isle Place, Holiday, FL 34691
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  /2

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  5710 Golden Nugget Dr, Holiday, FL 34690

  5710 Golden Nugget Dr, Holiday, FL 34690
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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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  $1,099 - $1,499 per month

  Sunbay Apartments

  1 - 2 Beds

  4348 Plaza Dr, Holiday, FL 34691

  Come home to the quiet relaxation of The Sunbay Apartments. Private and luxurious, this is a haven with numerous amenities. Sunbay Apartments is perfectly located near major Highways with access to downtown, shopping, medical facilities, and recreation. Available for your convenience are 3 swimming pools, clubhouse, and New Playground as well as a dog park! Experience the ease of deluxe

  4348 Plaza Dr, Holiday, FL 34691
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  /2

  $170,000 Sold Sep 23, 2025

  3136 Birkdale Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $147/SF
  • 33 Days On Market

  Last Listing Agent Stella Wooster CITY BREEZE ACTION REALTY

  3136 Birkdale Dr, Holiday, FL 34690
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  /2

  Est $376,963 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,688 Sq Ft

  2014 Cove Ct, Holiday, FL 34691

  2014 Cove Ct, Holiday, FL 34691
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  $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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  /13

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • House for Rent

  2043 Shannon Dr, Holiday, FL 34690

  This charming 3-bedroom, 2-bath home features tile flooring throughout, spacious bedrooms, and fresh interior and exterior paint. Recent updates include a new septic tank and a fully fenced backyard—perfect for privacy and outdoor enjoyment. Conveniently located near shopping, dining, and everyday essentials. Enjoy relaxing evenings on the screened lanai.

  Kim Doukas CHARLES RUTENBERG REALTY INC

  2043 Shannon Dr, Holiday, FL 34690
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  /2

  $235,000 Sold Jun 20, 2025

  3445 Pinehurst Dr, Holiday, FL 34691

  • 3 Beds
  • 1 Bath
  • 1,014 Sq Ft
  • Built 1965

  Last Sold Summary

  • $232/SF
  • 4 Days On Market

  Current Estimated Value $226,856

  Last Listing Agent Josh Jacobs FUTURE HOME REALTY INC

  3445 Pinehurst Dr, Holiday, FL 34691
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  /2

  Est $206,466 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,304 Sq Ft

  3336 Rosefield Dr, Holiday, FL 34691

  3336 Rosefield Dr, Holiday, FL 34691
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  $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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  /16

  $1,735 per month

  • 3 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • House for Rent

  1103 Chelsea Ln, Holiday, FL 34691

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  1103 Chelsea Ln, Holiday, FL 34691
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  /2

  $380,000 Sold Jun 26, 2025

  2749 Plantain Dr, Holiday, FL 34691

  • 4 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $209/SF
  • 129 Days On Market

  Current Estimated Value $388,470

  Last Listing Agent Barbara Ann Grady, PA CHARLES RUTENBERG REALTY INC

  2749 Plantain Dr, Holiday, FL 34691
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  /2

  Est $233,199 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  3338 Trask Dr, Holiday, FL 34691

  3338 Trask Dr, Holiday, FL 34691
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  $220,000

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft

  3518 Umber Rd, Holiday, FL 34691

  4 Bedroom, 2 Bathroom 1 car garage block home in desirable Holiday Florida. The most affordable 4-bedroom listing in Holiday at time of posting—featuring an attached garage and a large fenced-in backyard. The interior includes ceramic tile and vinyl flooring—no carpet—along with a spacious living room, ceiling fans, window blinds, central AC and heat, kitchen with glass-top range, refrigerator,

  

  Randal Jenkins

  FLORIDA REAL ESTATE PARTNERS

  (727) 607-6658

  3518 Umber Rd, Holiday, FL 34691
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  /19

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • House for Rent

  3110 Rock Valley Dr, Holiday, FL 34691

  PERFECT FAMILY HOME CALL TO SEE TODAY

  Florence Lugo FLO LUGO REALTY INC

  3110 Rock Valley Dr, Holiday, FL 34691
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  /2

  $257,500 Sold Apr 02, 2025

  5331 Skyland Dr, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 1971

  Last Sold Summary

  • 6% Below List Price
  • $202/SF
  • 148 Days On Market

  Current Estimated Value $260,021

  Last Listing Agent Cindy Greco EXP REALTY LLC

  5331 Skyland Dr, Holiday, FL 34690
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  /2

  Est $191,001 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft

  5027 Farley Dr, Holiday, FL 34690

  5027 Farley Dr, Holiday, FL 34690
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  $151,500

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft

  4324 Tahitian Gardens Cir Unit J, Holiday, FL 34691

  WATERFRONT, 2-bedroom, bath-and-a-half condo in the gated 55+ community of Tahitian Gardens. Enjoy stunning water views from the oversized living room windows and outside patio. This property features separate kitchen and dining areas. Both bedrooms are generously sized with updated windows and newer carpet. The primary bedroom includes a half bath and a walk-in closet. A full-sized, all-tile

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 291-9310

  4324 Tahitian Gardens Cir Unit J, Holiday, FL 34691
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  /3

  $1,699 per month

  • 2 Beds
  • 1 Bath
  • 1,360 Sq Ft
  • House for Rent

  2412 Arcadia Rd, Holiday, FL 34690

  Discover this inviting single-family rental offering ample living space with modern finishes. This property features a fenced yard and an attached garage.- Includes microwave, electric range, and refrigerator- Efficient heat pump and central cooling and heating- Attractive tile and wood plank floors throughout- Convenient in-unit laundry area- Secure, attached garage

  2412 Arcadia Rd, Holiday, FL 34690
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  $229,900 Sold Apr 14, 2025

  3403 Garfield Dr, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1978

  Last Sold Summary

  • $282/SF
  • 4 Days On Market

  Current Estimated Value $226,977

  Last Listing Agent Wayne Gabriel RE/MAX PREMIER GROUP

  3403 Garfield Dr, Holiday, FL 34691
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  /2

  Est $304,378 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  3249 Chauncy Rd, Holiday, FL 34691

  3249 Chauncy Rd, Holiday, FL 34691
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  $175,000

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  3846 Bywater Dr, Holiday, FL 34691

  WATERFRONT LIVING... KAYAKER'S DELIGHT... GATED COMMUNITY... DRY DURING RECENT HURRICANE SEASONS... Welcome to 3846 Bywater Dr, a rare gem nestled in the vibrant 55+ gated community of Lake Conley, where the pace is easy, the people are welcoming, and every day feels like a mini vacation. This 2-bedroom, 2-bath home sits directly on the water and offers your own private area to build a new dock,

  

  Scott Morris

  EXP REALTY LLC

  (727) 428-2054

  3846 Bywater Dr, Holiday, FL 34691
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  /14

  $1,600 per month

  • 3 Beds
  • 2 Baths
  • 972 Sq Ft
  • House for Rent

  4005 Dalwood Dr, Holiday, FL 34691

  Cute 3 bedroom home, new ceramic tile through out the home. Fresh paint $75 App fee/adult, $300 non-refundable pet fee/ pet, security deposit equal to one month's rent, $75 tenant annual processing fee/ household after acceptance, renters insurance required.

  Wanda Burnside DENNIS REALTY PROPERTY MGMT.

  4005 Dalwood Dr, Holiday, FL 34691
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  $21,900 Sold Jan 02, 2026

  4699 Continental Dr Unit 309, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • Built 1984

  Last Sold Summary

  • 17 Days On Market

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

  4699 Continental Dr Unit 309, Holiday, FL 34690
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  /2

  Est $255,179 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  5428 Baroque Dr, Holiday, FL 34690

  5428 Baroque Dr, Holiday, FL 34690
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  /55

  $280,000

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft

  2907 Narcissus Dr, Holiday, FL 34691

  Priced to sell and well maintained. This clean 2-bedroom, 2-bath home offers large rooms, a comfortable layout, and updates where they matter. Newer laminate flooring runs through the main living areas, and the updated kitchen features stainless steel appliances, quartz countertops, and ample cabinetry. The primary bedroom includes a generous walk-in closet, and the second bathroom has been

  

  Michael Pappas

  PAPPAS REAL ESTATE LLC

  (727) 387-4315

  2907 Narcissus Dr, Holiday, FL 34691
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  /17

  $1,995 per month

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

  5177 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

  5177 Forum Blvd, Holiday, FL 34690
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  $231,000 Sold Feb 14, 2025

  4823 Longwood Ave, Holiday, FL 34690

  • 3 Beds
  • 1 Bath
  • 1,122 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Below List Price
  • $206/SF
  • 217 Days On Market

  Current Estimated Value $236,284

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  4823 Longwood Ave, Holiday, FL 34690
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  /2

  Est $275,786 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,388 Sq Ft

  3411 Paloma Dr, Holiday, FL 34690

  3411 Paloma Dr, Holiday, FL 34690
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  $180,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  2101 Hilo Dr, Holiday, FL 34691

  Wow! What a well-maintained 2-bedroom, 2-bath home with carport and screened porch, located in the gated 55+ community of Lake Conley. All furniture and furnishings are optional. This inviting double-wide manufactured home offers strong curb appeal with neutral siding, a bank of bright double-pane windows, mature landscaping, paved driveway (2021), and a covered carport complemented by a screened

  

  Jodi Avery

  KELLER WILLIAMS SOUTH TAMPA

  (727) 380-6830

  2101 Hilo Dr, Holiday, FL 34691
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  /31

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,345 Sq Ft
  • House for Rent

  5315 Sparrow Dr, Holiday, FL 34690

  FURNISHED or UNFURNISHED BEAUTIFUL RENTAL HOME WITH HEATED IN-GROUND POOL!!! This stunning totally remodeled single family home is sure to captivate your heart with its charm and unique character. The open floor plan creates a spacious and inviting atmosphere. Sleek electric modern fireplace enhances the living room with contemporary style and cozy ambience. The kitchen features stainless steel

  Grace Omyla PROPERTY LEADERS RE INC

  5315 Sparrow Dr, Holiday, FL 34690
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  $250,000 Sold Feb 18, 2025

  1132 Clairborne St, Holiday, FL 34690

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1963

  Last Sold Summary

  • 7% Below List Price
  • $306/SF
  • 68 Days On Market

  Current Estimated Value $237,969

  Last Listing Agent Randys Oliva GOLD REAL ESTATE SOLUTIONS

  1132 Clairborne St, Holiday, FL 34690
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  /2

  Est $343,417 Not Listed For Sale

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

  3247 Hoover Dr, Holiday, FL 34691

  3247 Hoover Dr, Holiday, FL 34691

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