18,320

Holiday, FL Homes

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  • /28

    $179,000 Pending

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    3518 Emory Dr, Holiday, FL 34691

    Under contract-accepting backup offers. BACK ON MARKET due to buyer's inability to secure down payment assistance.Charming home full of potential and solid bones — perfect as a starter home, renovation project, or investment opportunity.NO HOA and NO FLOOD ZONE. 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

    Agent Photo

    Andzelika Duraj

    FUTURE HOME REALTY INC

    (727) 855-3218

    3518 Emory Dr, Holiday, FL 34691
  • /16

    $1,955 per month

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft
    • House for Rent

    3511 Sheryl Hill Dr, 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.

    3511 Sheryl Hill Dr, Holiday, FL 34691
  • /2

    $378,900 Sold Jul 07, 2025

    1650 Springdale Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Built 1975

    Last Sold Summary

    • 2% Above List Price
    • $263/SF
    • 7 Days On Market

    Current Estimated Value $357,352

    Last Listing Agent Taylor Sparling SELECT PROPERTIES INC

    1650 Springdale Dr, Holiday, FL 34691
    • /2

      Est $265,481 Not Listed For Sale

      3627 Ortona Dr, Holiday, FL 34691

      • 2 Beds
      • 2 Baths
      • 1,542 Sq Ft
      • Built 1973
      3627 Ortona Dr, Holiday, FL 34691

      Last Sold Summary

      • 46% Above List Price
      • $118/SF
      • 243 Days On Market

      Last Sold Price $181,500

      Last Listing Agent Sten and Denise Tallarida FUTURE HOME REALTY INC

  • /68

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,004 Sq Ft

    3410 Pinehurst Dr, Holiday, FL 34691

    This is the one you’ve been waiting for!Welcome home to 3410 Pinehurst Drive in Holiday—a charming, truly move-in-ready home that shines from top to bottom. From the moment you step inside, you’re greeted by a beautifully maintained interior and thoughtful upgrades throughout.Home Highlights & Upgrades• Impact windows & impact doors (front door is solid wood & impact-rated)• Newer

    Mary Giasevits

    TRADEWIND PROPERTIES

    (727) 606-8047

    3410 Pinehurst Dr, Holiday, FL 34691
  • /7

    $1,600 per month

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft
    • House for Rent

    3445 Wiltshire Dr, Holiday, FL 34691

    NEWER KITCHEN AND INSIDE BATH WITH WHITE SHAKER CABINETS AND BEAUTIFUL GRANITE COUNTERTOPS. FULLY NEUTRAL COLOR TILED HOME WITH A SPACIOUS FLORIDA ROOM PERFECT FOR A HOME OFFICE OR GUEST AREA. NEW WINDOW IN THE LIVING ROOM. OVERSIZED 1 CAR GARAGE WITH WASHER/DRYER HOOKUP, 1/2 BATH A SHOWER & TOILET) AND GARAGE DOOR OPENER. FULLY FENCED BACKYARD AND LARGE STORAGE ROOM. $50 APPLICATION FEE PER

    Julie Pitta PITTA AND ASSOC INC

    3445 Wiltshire Dr, Holiday, FL 34691
  • /2

    $240,000 Sold Apr 07, 2025

    4900 Colonnade Ave, Holiday, FL 34690

    • 2 Beds
    • 1.5 Baths
    • 996 Sq Ft
    • Built 1964

    Last Sold Summary

    • $241/SF
    • 2 Days On Market

    Current Estimated Value $232,880

    Last Listing Agent Christa Setzer SIGNATURE REALTY ASSOCIATES

    4900 Colonnade Ave, Holiday, FL 34690
    • /2

      Est $224,863 Not Listed For Sale

      2415 Roselawn Dr, Holiday, FL 34691

      • 2 Beds
      • 1.5 Baths
      • 1,128 Sq Ft
      • Built 1968
      2415 Roselawn Dr, Holiday, FL 34691

      Last Sold Summary

      • 2% Below List Price
      • $204/SF
      • 146 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Yoicy Milian HOME PRIME REALTY LLC

  • /53

    $312,000

    • 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

    Agent Photo

    Rick Bishop

    LPT REALTY, LLC

    (727) 624-1893

    3238 Coldwell Dr, Holiday, FL 34691
  • /16

    $1,640 per month

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • House for Rent

    3916 Darlington Rd, 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.

    3916 Darlington Rd, Holiday, FL 34691
  • /2

    $110,000 Sold Nov 25, 2025

    4834 Mile Stretch Dr, Holiday, FL 34690

    • 2 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 1962

    Last Sold Summary

    • 12% Below List Price
    • $100/SF
    • 2 Days On Market

    Current Estimated Value $110,264

    Last Listing Agent Jacqueline Filippi BHHS FLORIDA PROPERTIES GROUP

    4834 Mile Stretch Dr, Holiday, FL 34690
    • /2

      Est $177,628 Not Listed For Sale

      3543 Cheswick Dr, Holiday, FL 34691

      • 2 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1968
      3543 Cheswick Dr, Holiday, FL 34691

      Last Sold Summary

      • 8% Above List Price
      • $164/SF
      • 212 Days On Market

      Last Sold Price $165,000

      Last Listing Agent Dave Treloar, Jr LATIMER & ASSOCIATES REALTY

  • /11

    $99,900 Pending

    • Land
    • 0.24 Acre
    • $416,250 per Acre

    5251 Boardwalk St, Holiday, FL 34690

    **OWNER FINANCING AVAILABLE WITH QUALIFIED DOWN PAYMENT** Discover the perfect opportunity to build your dream waterfront home on this vacant canal-front lot. Featuring a sturdy seawall already in place, this property offers peace of mind and easy access for future dock or boat lift installation. With direct water frontage, you'll enjoy scenic views, relaxing breezes, and the chance to design a

    Agent Photo

    Terisha Miller

    Realty Executive America, Inc

    (727) 766-9848

    5251 Boardwalk St, Holiday, FL 34690
  • /19

    $1,595 per month

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • House for Rent

    4018 Kibler Ln, Holiday, FL 34691

    Available May 1st! Welcome yourself into this updated 1966 home! Located on a corner lot, this home has 2 bedrooms, 2 bathrooms (spare bathroom located in the garage), and 1 car garage. Included in this home is a stove/oven, fridge, dishwasher, island, new flooring in the bedrooms, fenced in back yard, screened in front patio, stack washer and dryer (for tenant convenience only), and central heat

    Mallory Olivero Dennis Realty & Investment Corp.

    4018 Kibler Ln, Holiday, FL 34691
  • /2

    $213,500 Sold Jan 31, 2026

    3743 Lomi Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • Built 2021

    Last Sold Summary

    • 5% Below List Price
    • $158/SF
    • 37 Days On Market

    Last Listing Agent Diana Schlafley CHARLES RUTENBERG REALTY INC

    3743 Lomi Dr, Holiday, FL 34691
    • /21

      Est $233,517 Not Listed For Sale

      4332 Beacon Square Dr, Holiday, FL 34691

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1965
      4332 Beacon Square Dr, Holiday, FL 34691

      Last Sold Summary

      • 5% Below List Price
      • $284/SF
      • 108 Days On Market

      Last Sold Price $245,000

      Last Listing Agent KIERSTIN BALDWIN-CHASE COLDWELL BANKER REALTY

  • /54

    $265,000

    • 2 Beds
    • 2 Baths
    • 1,125 Sq Ft

    5930 Della Dr, Holiday, FL 34690

    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

    Agent Photo

    Georgete Frey

    DALTON WADE INC

    (727) 339-7484

    5930 Della Dr, Holiday, FL 34690
  • /11

    $1,870 per month

    • 2 Beds
    • 2 Baths
    • 1,042 Sq Ft
    • House for Rent

    3535 Devonshire Dr, Holiday, FL 34691

    This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).

    3535 Devonshire Dr, Holiday, FL 34691
  • /2

    $220,000 Sold Sep 29, 2025

    6141 Staunton Dr, Holiday, FL 34690

    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $195/SF
    • 5 Days On Market

    Current Estimated Value $220,849

    Last Listing Agent Chris Sakamoto MARK SPAIN REAL ESTATE

    6141 Staunton Dr, Holiday, FL 34690
    • /37

      Est $292,542 Not Listed For Sale

      3507 Chauncy Rd, Holiday, FL 34691

      • 3 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1973
      3507 Chauncy Rd, Holiday, FL 34691

      Last Sold Summary

      • 4% Below List Price
      • $223/SF
      • 96 Days On Market

      Last Sold Price $305,000

      Last Listing Agent David Garcia REAL BROKER, LLC

  • /40

    $89,900

    • 2 Beds
    • 1.5 Baths
    • 857 Sq Ft

    1917 Hess Dr, Holiday, FL 34691

    Owner financing will be considered.This two-bedroom, one-bathroom house offers approximately 857 square feet of living space. The property features a covered carport, providing convenient covered parking. Additionally, there is a work shed on the property that includes a washer and dryer for added convenience. The low homeowner's association (HOA) fees make this an attractive option for those

    Agent Photo

    Jennifer Zulian

    COLDWELL BANKER REALTY

    (727) 604-7046

    1917 Hess Dr, Holiday, FL 34691
  • /28

    $2,350 per month

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft
    • House for Rent

    4036 Sunray Dr, Holiday, FL 34691

    FOR LEASE – Enjoy peaceful lakefront living in this beautifully updated three-bedroom, two-bathroom home in Holiday. With a spacious driveway, one-car garage, and inviting large front porch, this home offers both curb appeal and everyday convenience. Inside, you’ll find stunning luxury plank flooring and a bright, functional layout. The dining room and kitchen combination is perfect for

    Jeffrey Borham EXP REALTY LLC

    4036 Sunray Dr, Holiday, FL 34691
  • /2

    $400,000 Sold Apr 21, 2025

    2230 Indian Key Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 2003

    Last Sold Summary

    • 11% Below List Price
    • $228/SF
    • 440 Days On Market

    Current Estimated Value $388,397

    Last Listing Agent Paul Virgadamo EXP REALTY LLC

    2230 Indian Key Dr, Holiday, FL 34691
    • /24

      Est $220,520 Not Listed For Sale

      2349 Grandin St, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 956 Sq Ft
      • Built 1963
      2349 Grandin St, Holiday, FL 34690

      Last Sold Summary

      • 2% Below List Price
      • $235/SF
      • 45 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Aaron Gross PINEYWOODS REALTY LLC

  • /51

    $549,900 Pending

    • 4 Beds
    • 3 Baths
    • 1,761 Sq Ft

    1166 Chancellor Dr, Holiday, FL 34690

    Under contract-accepting backup offers. Stunning fully remodeled 4-bedroom, 3-bath waterfront home offering privacy, functionality, and true Gulf-access living. This exceptional property has remained high and dry with no flooding during recent storms, providing peace of mind along with an unbeatable natural setting. Set along a scenic bend of the river, the backyard overlooks a private island

    Agent Photo

    Shawn Poole

    SNAP REALTY LLC

    (727) 497-7642

    1166 Chancellor Dr, Holiday, FL 34690
  • /16

    $2,170 per month

    • 3 Beds
    • 2 Baths
    • 1,854 Sq Ft
    • House for Rent

    2026 Tumbleweed Dr, Holiday, FL 34690

    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.

    2026 Tumbleweed Dr, Holiday, FL 34690
  • /2

    $139,000 Sold Jun 03, 2025

    1731 Dander Dr, Holiday, FL 34690

    • 2 Beds
    • 1.5 Baths
    • 1,032 Sq Ft
    • Built 1968

    Last Sold Summary

    • 13% Below List Price
    • $135/SF
    • 31 Days On Market

    Current Estimated Value $155,042

    Last Listing Agent Randal Jenkins FLORIDA REAL ESTATE PARTNERS

    1731 Dander Dr, Holiday, FL 34690
    • /2

      Est $299,991 Not Listed For Sale

      3235 Merita Dr, Holiday, FL 34691

      • 3 Beds
      • 2 Baths
      • 1,672 Sq Ft
      • Built 1970
      3235 Merita Dr, Holiday, FL 34691

      Last Sold Summary

      • $179/SF
      • 12 Days On Market

      Last Sold Price $299,900

      Last Listing Agent Morgan Munger CHARLES RUTENBERG REALTY INC

  • /27

    $85,000

    • 2 Beds
    • 1.5 Baths
    • 890 Sq Ft

    2107 Melody Dr, Holiday, FL 34691

    Welcome to your sun-drenched retreat in Hudson, Florida! This well-maintained 2-bedroom, 1.5-bathroom double-wide mobile home offers the perfect blend of comfort and classic Florida charm. Inside, you’ll find an open-concept living area featuring beautiful laminate flooring and vaulted ceilings. The bright, clean kitchen includes a convenient breakfast bar that flows into the dining space, while

    Agent Photo

    Jackie Little

    KELLER WILLIAMS REALTY- PALM H

    (727) 761-7329

    2107 Melody Dr, Holiday, FL 34691
  • /30

    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 861 Sq Ft
    • House for Rent

    3405 Wilson Dr, Holiday, FL 34691

    Furnished and Fully renovated two-bedroom, one-bath single family home. The renovated interior, offers a modern and inviting living space. The updates include appliances, flooring, paint, lighting fixture, plumbing fixtures, blinds, vanity, countertops and provide a comfortable and stylish home environment. The fence in backyard is private and a great area to relax. The sewer and trash pickup

    Jeffrey Stuben DALTON WADE INC

    3405 Wilson Dr, Holiday, FL 34691
  • /2

    $215,000 Sold Jul 23, 2025

    3234 Jackson Dr, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 1979

    Last Sold Summary

    • 20% Below List Price
    • $189/SF
    • 263 Days On Market

    Current Estimated Value $219,038

    Last Listing Agent John Scalia EXP REALTY LLC

    3234 Jackson Dr, Holiday, FL 34691
    • /23

      Est $239,347 Not Listed For Sale

      5305 Bob White Dr, Holiday, FL 34690

      • 3 Beds
      • 1 Bath
      • 1,284 Sq Ft
      • Built 1972
      5305 Bob White Dr, Holiday, FL 34690

      Last Sold Summary

      • 1% Above List Price
      • $184/SF
      • 50 Days On Market

      Last Sold Price $235,870

      Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  • /53

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,018 Sq Ft

    3426 Kimberly Oaks Dr, Holiday, FL 34691

    One or more photo(s) has been virtually staged. 30k PRICE IMPROVEMENT! Priced to sell!! Welcome to this well-priced 3 bedroom, 2 bathroom, 1 car garage home located in the heart of Holiday, Florida. This property offers all new kitchen appliances with convenience, comfort, and an ideal location for first-time buyers or those looking to downsize. Situated close to the Gulf, you’ll enjoy quick

    Agent Photo

    David McCollum

    REALTY EXPERTS

    (727) 361-6006

    3426 Kimberly Oaks Dr, Holiday, FL 34691
  • /16

    $1,890 per month

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

    5141 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 $2059.90. That covers your base rent, $1890.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    5141 Forum Blvd, Holiday, FL 34690
  • /2

    $270,000 Sold Feb 06, 2026

    3243 Eisenhower Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft
    • Built 1972

    Last Sold Summary

    • $203/SF
    • 26 Days On Market

    Current Estimated Value $261,811

    Last Listing Agent Dan Risola RE/MAX REALTEC GROUP INC

    3243 Eisenhower Dr, Holiday, FL 34691
    • /21

      Est $199,118 Not Listed For Sale

      5026 Flora Ave, Holiday, FL 34690

      • 2 Beds
      • 1.5 Baths
      • 1,157 Sq Ft
      • Built 1968
      5026 Flora Ave, Holiday, FL 34690

      Last Sold Summary

      • 6% Above List Price
      • $162/SF
      • 67 Days On Market

      Last Sold Price $187,500

      Last Listing Agent Matthew Brashear RE/MAX

  • /8

    $99,900

    • Land
    • 0.16 Acre
    • $624,375 per Acre

    5247 Boardwalk St, Holiday, FL 34690

    **OWNER FINANCING AVAILABLE WITH QUALIFIED DOWN PAYMENT** Discover the perfect opportunity to build your dream waterfront home on this vacant canal-front lot. Featuring a sturdy seawall already in place, this property offers peace of mind and easy access for future dock or boat lift installation. With direct water frontage, you'll enjoy scenic views, relaxing breezes, and the chance to design a

    Agent Photo

    Terisha Miller

    Realty Executive America, Inc

    (727) 496-7752

    5247 Boardwalk St, Holiday, FL 34690
  • /11

    $1,690 per month

    • 2 Beds
    • 1.5 Baths
    • 1,234 Sq Ft
    • Townhouse for Rent

    3633 Rock Royal Dr Unit 1, Holiday, FL 34691

    Welcome to your remodeled home in Holiday! This charming 2-bedroom, 1-bath residence features an open layout, modern finishes, and abundant natural light throughout. Enjoy a brand-new feel with updated kitchen, bathroom, flooring, and fresh paint. The property offers 2 convenient open parking spaces and a relaxing backyard with water views that create a truly peaceful atmosphere. Ideally located

    zulmad Antolinez HABLOFT GLOBAL

    3633 Rock Royal Dr Unit 1, Holiday, FL 34691
  • /2

    $240,000 Sold Apr 25, 2025

    4733 Bonton Dr, Holiday, FL 34690

    • 2 Beds
    • 1 Bath
    • 1,046 Sq Ft
    • Built 1964

    Last Sold Summary

    • 2% Below List Price
    • $229/SF
    • 12 Days On Market

    Current Estimated Value $231,070

    Last Listing Agent Mark Hangen MIHARA & ASSOCIATES INC.

    4733 Bonton Dr, Holiday, FL 34690
    • /2

      Est $333,547 Not Listed For Sale

      5117 Roanoke Dr, Holiday, FL 34690

      • 3 Beds
      • 2 Baths
      • 1,630 Sq Ft
      • Built 1984
      5117 Roanoke Dr, Holiday, FL 34690

      Last Sold Summary

      • 1% Above List Price
      • $202/SF
      • 24 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Janice Mason COASTAL PROPERTIES GROUP INTERNATIONAL

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