Old Naples Houses for Rent

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  $55,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,850 Sq Ft
  • House for Rent

  300 2nd Ave N, Naples, FL 34102

  BOOKED FROM JAN. 1- April 30, 2025'. This furnished house, designed by MHK Architect, is perfectly situated just 2 blocks to the beach and a short stroll to Fifth Ave. Open floor plan with 370 Sq. Ft. of sliding pocketed doors to maximize the Florida outdoor living experience. With all important southern exposure, the sun lights up the home. Four bedrooms, a huge bonus room, wide wood plank

  Marjorie Workinger Royal Shell Real Estate, Inc.

  300 2nd Ave N, Naples, FL 34102
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  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 2,252 Sq Ft
  • House for Rent

  359 2nd Ave N, Naples, FL 34102

  BOOKED Jan.-March 2025: This charming Old Naples house has a perfect combination of great location, serene outdoor spaces, and a spacious, updated interior. The house is 2.5 blocks to the beach, a short bike ride to 5th Ave. S., as a well as the local grocery so leaving the car in the three - car garage is optional. Magnificent outdoor spaces make this home a private oasis. Spend the day by the

  Marjorie Workinger Royal Shell Real Estate, Inc.

  359 2nd Ave N, Naples, FL 34102
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  /22

  $38,000 per month

  • 3 Beds
  • 3 Baths
  • 3,050 Sq Ft
  • House for Rent

  680 8th Ave S, Naples, FL 34102

  Annual rate is $28,500 per month. Listed rate is for High Season (December through April). Longer leases have greater discounted rates. See rental rate sheet. Located just steps to Cambier Park, 5th Avenue South, Third Street South, and Naples' famous beaches, the 1929 Captain Parker House is unequivocally filled with every ounce of history, charm, and luxury one would desire! Numerous

  Bill Earls John R Wood Properties

  680 8th Ave S, Naples, FL 34102
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  $40,000 per month

  • 3 Beds
  • 3 Baths
  • 2,776 Sq Ft
  • House for Rent

  444 2nd Ave N, Naples, FL 34102

  Discover timeless charm with a front porch perfect for morning coffee or evening breezes in the heart of Olde Naples! This two-story gem, just several blocks from the beach, offers a unique blend of character and coastal allure. Inside, find 3 bedrooms, a flexible den, and an open, sunlit layout that combines Old Florida charm with modern comforts. Step outside to enjoy your private pool and spa,

  Connie Kommer William Raveis Real Estate

  444 2nd Ave N, Naples, FL 34102
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  $35,000 per month

  • 4 Beds
  • 3 Baths
  • 2,488 Sq Ft
  • House for Rent

  370 6th Ave S, Naples, FL 34102

  Nestled in the heart of Olde Naples, this exquisite 4-bedroom, 3-bathroom home offers the perfect blend of luxury, privacy, and convenience. With its prime location just one block from the bustling 5th Avenue and three blocks from the pristine beaches, you'll have the best of both worlds: the tranquility of a private oasis and the excitement of a vibrant coastal town.As you step through

  Michael Dedio Naples Trust Real Estate Servi

  370 6th Ave S, Naples, FL 34102
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  $45,000 per month

  • 3 Beds
  • 3.5 Baths
  • 3,325 Sq Ft
  • House for Rent

  12 6th St S, Naples, FL 34102

  Welcome to Naples Coastal Retreat – Your Luxurious Getaway! Experience the epitome of coastal contemporary living at our stunning vacation rental home in beautiful Naples, FL. This exquisite three-bedroom sanctuary, each with its own attached bathroom, offers the perfect blend of luxury, comfort, and style, making it an ideal retreat for families or groups of friends. Each of the three spacious

  Michael Dedio Naples Trust Real Estate Servi

  12 6th St S, Naples, FL 34102
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  $58,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,229 Sq Ft
  • House for Rent

  380 5th Ave N, Naples, FL 34102

  Experience life in one of Naples' most pleasant neighborhoods just steps to the beach! Southern Sunset is a newly renovated and designer decorated coastal style home with all of the features and amenities you're searching for. Enter from the circular drive into an open living room with views out to the southern exposure lanai, heated pool and hot tub. A new picture window screen enclosure

  Stacey Cotter John R Wood Properties

  380 5th Ave N, Naples, FL 34102
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  $58,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,229 Sq Ft
  • House for Rent

  380 5th Ave N, Naples, FL 34102

  Experience life in one of Naples' most pleasant neighborhoods just steps to the beach! Southern Sunset is a newly renovated and designer decorated coastal style home with all of the features and amenities you're searching for. Enter from the circular drive into an open living room with views out to the southern exposure lanai, heated pool and hot tub. A new picture window screen enclosure

  Stacey Cotter John R Wood Properties

  380 5th Ave N, Naples, FL 34102
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  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,930 Sq Ft
  • House for Rent

  271 1st Ave S, Naples, FL 34102

  Annual Rate is $22,500 per month. Listed rate is for High Season (Nov.-April). Longer High Season leases have greater discounted rates. Ideally located, this is the quintessential Olde Naples cottage home in a tropical, park-like setting only two and a half blocks to the beach. Cute, charming, and pristine, this three-bedroom home is the perfect Naples escape. Pets welcome! Only a short walk to

  Bill Earls John R Wood Properties

  271 1st Ave S, Naples, FL 34102
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  $42,500 per month

  • 4 Beds
  • 4 Baths
  • 3,702 Sq Ft
  • House for Rent

  431 1st Ave N, Naples, FL 34102

  Annual Rate is $31,875 per month. Listed rate is for High Season (Nov.-April). Longer High Season leases have greater discounted rates. Ideally situated on a quiet, mahogany lined street in the heart of Downtown Olde Naples sits this custom 4-bedroom home with a very accommodating floorplan. Freshly updated and decorated. Features include including wood floors throughout, hurricane impact

  Bill Earls John R Wood Properties

  431 1st Ave N, Naples, FL 34102
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  $45,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,434 Sq Ft
  • House for Rent

  195 2nd Ave N, Naples, FL 34102

  Annual Rate is $33,750 per month. Listed Rate is for high-season (Nov.-April). Longer high-season leases have greater discounted rates. The epitome of whimsical beach town living! Nestled only two blocks to the sugar sand coastline on a lush-tree lined street is this charmingly renovated two-story residence. Hosting five bedrooms + den, five full and one half bathrooms, and a number of other

  Bill Earls John R Wood Properties

  195 2nd Ave N, Naples, FL 34102
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  $42,000 per month

  • 4 Beds
  • 3 Baths
  • 2,216 Sq Ft
  • House for Rent

  206 1st Ave N, Naples, FL 34102

  Annual rate is $31,500. Listed Rate is for High Season (Nov. through April). Longer lease terms have greater discounted rates. Charming in every respect, this cottage is located a mere minute's walk to the beach! The residence features four spacious bedrooms, three renovated bathrooms, a fireplace, as well as multiple clean and bright living spaces. Located beyond the rear of the home's French

  Bill Earls John R Wood Properties

  206 1st Ave N, Naples, FL 34102
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  $42,750 per month

  • 4 Beds
  • 4.5 Baths
  • 3,100 Sq Ft
  • House for Rent

  354 1st Ave N, Naples, FL 34102

  Annual Rate is $32K per month. Listed rate is for High Season (November through April). Longer High Season leases have greater discounted rates. Nestled one of Olde Naples most picturesque tree-lined streets, and just three short blocks to sugar sand beaches, this idyllic and private residence affords 3,100 square feet of everything one could desire. The interior of the residence is dressed in

  Bill Earls John R Wood Properties

  354 1st Ave N, Naples, FL 34102
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  $54,000 per month

  • 5 Beds
  • 6.5 Baths
  • 5,641 Sq Ft
  • House for Rent

  Unlisted Address

  Annual rate is $40,500 per month. Listed rate is for High Season (Nov. through April). Longer High Season leases have greater discounted rates. See attached rate sheet. Located only two blocks to the beach and featuring lush, mature tropical foliage, this classic Bermuda styled home offers absolutely stunning interiors. The sprawling residence hosts five bedrooms, a study, as well as a flex space

  Bill Earls John R Wood Properties

  Unlisted Address
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  $47,250 per month

  • 4 Beds
  • 4.5 Baths
  • 3,815 Sq Ft
  • House for Rent

  168 2nd Ave N, Naples, FL 34102

  Annual rate is $35K per month. Advertised rate is for high-season (Nov. through April); longer lease terms have greater discounted rates. This Old Naples Cottage home is a perfect union of style and function and is situated just three doors to the beach on a lushly landscaped lot. As you enter you are greeted by beautiful tongue and groove cathedral ceilings, custom millwork, and vintage pendant

  Bill Earls John R Wood Properties

  168 2nd Ave N, Naples, FL 34102
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  $48,000 per month

  • 5 Beds
  • 4.5 Baths
  • 5,132 Sq Ft
  • House for Rent

  194 4th Ave N, Naples, FL 34102

  The annual rate is $36,000.00 / month. The advertised rate is for high-season (Nov.-April); longer terms have greater discounted rates. Situated only four houses from Naples’ sugar sand beaches on an oversized lot offering the utmost this home represents the quintessential tropical retreat! The residence features Old-Florida architecture, a metal roof, Hardi Plank siding, a front porch, wood

  Bill Earls John R Wood Properties

  194 4th Ave N, Naples, FL 34102
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  $55,000 per month

  • 4 Beds
  • 6 Baths
  • 3,909 Sq Ft
  • House for Rent

  434 3rd Ave S, Naples, FL 34102

  Arguably the best location for a rental in Olde Naples! Only 3 blocks from the white sandy beaches that make Naples one of the most desired locations in FL. This dream home boasts nearly 5,000 square feet with heated pool, southern exposure, and 4 Clive Daniel decorated bedrooms, each with its own en suite bath. One bedroom features four floating bunks, each with a privacy curtain, lamp and

  Todd Culmer Waterfront Realty Group Inc

  434 3rd Ave S, Naples, FL 34102
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  $24,000 per month

  • 3 Beds
  • 2 Baths
  • 2,097 Sq Ft
  • House for Rent

  150 1st Ave N, Naples, FL 34102

  The perfect beach cottage! This classic Olde Naples home has been completely renovated to offer comfort and coastal style in an ideal location along tree-lined 1st Ave N, just three houses from the beach. Walk out your front door to catch nightly sunsets or enjoy early morning beach walks to welcome another beautiful day in paradise. Inside the house, you will find three beautifully appointed

  Stacey Cotter John R Wood Properties

  150 1st Ave N, Naples, FL 34102
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  $14,000 per month

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • House for Rent

  678 E Lake Dr, Naples, FL 34102

  IF YOU ARE LOOKING FOR A SUPERB LOCATION WITH GREAT VIEWS OVERLOOKING SPRING LAKE WE MIGHT HAVE JUST FOUND YOU A GEM! THIS VINTAGE HOME IS WITHIN WALKING DISTANCE OF FIFTH AVENUE, DOWNTOWN, TIN CITY, BEAUTIFUL NAPLES BEACHES, BAYFRONT, SHOPPING, AND MORE. SPRING LAKE HAS BEEN MOSTLY RE-DEVELOPED, YET THIS HIDDEN GEM REMAINS. AFFORDABLE OPPORTUNITIES TO RENT ON SPRING LAKE DO NOT EXIST, OTHER THAN

  Gerald Mathusek Downing Frye Realty Inc.

  678 E Lake Dr, Naples, FL 34102
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  $28,000 per month

  • 4 Beds
  • 4 Baths
  • 2,691 Sq Ft
  • House for Rent

  223 11th Ave S, Naples, FL 34102

  Olde Naples Oasis is a short walk to the beautiful Gulf of Mexico! Nestled in a non-gated coastal neighborhood, this 2-story home with a Key West ambiance is the ideal place to relax & unwind enjoying the Florida sun. Situated right next to Naples 5th Ave AND 3rd Street South where you can find world-famous shopping & dining, plus a 2-block walk or bike ride to the gorgeous beach that lines the

  Stacey Cotter John R Wood Properties

  223 11th Ave S, Naples, FL 34102
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  $65,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,145 Sq Ft
  • House for Rent

  154 4th Ave N, Naples, FL 34102

  Coastal Chalet in Olde Naples - this stunning coastal dream is only a 2-min walk to the sparkling coastline of the Gulf of Mexico! This beautifully appointed home includes 4 bedrooms (two of them being primary suites), a centrally located study perfect for midday meetings, an upstairs den set up as a 2nd entertainment area, and an upstairs loft perfect for reading or cards. This vacation home is

  Stacey Cotter John R Wood Properties

  154 4th Ave N, Naples, FL 34102
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  $40,000 per month

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft
  • House for Rent

  860 7th St S, Naples, FL 34102

  Quintessential Olde Naples charm. Lovely, updated, pet-friendly, pool home, perfect for a luxurious vacation rental. and the entire outdoor living area is brand new. Owner has recently totally remodeled baths and kitchen area. Walk to 5th, to 3rd, to the beach and to the ASG tennis courts. Summer at $25000 per month. 90 day lease for 2026 at $40000 per month***Information contained herein

  Joe Hoopfer Premier Sotheby's Int'l Realty

  860 7th St S, Naples, FL 34102

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