Old Naples Houses for Rent

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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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  /14

  $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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  $10,795 per month

  • 2 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • House for Rent

  1325 Gordon Dr, Naples, FL 34102

  ** GORDON DRIVE FULLY REMODELED COTTAGE FOR SEASON ** 2/2 ** BLOCK AND HALF FROM THE BEACH ** LUXURY ** Welcome to the oldest Cottage on Gordon Drive. This STUNNING completely remodeled 2/2 Cottage comes fully stocked with everything NEW! Located in Prestigious Olde Naples, FL. This luxurious 2 bedroom, 2 bath Cottage is just a block and a half away from the beautiful Naples white powdery-sands

  Cheri Anne DeMonico Premier Property Management

  1325 Gordon Dr, Naples, FL 34102
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  /50

  $10,795 per month

  • 2 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • House for Rent

  1325 Gordon Dr, Naples, FL 34102

  ** GORDON DRIVE FULLY REMODELED COTTAGE FOR SEASON ** 2/2 ** BLOCK AND HALF FROM THE BEACH ** LUXURY ** Welcome to the oldest Cottage on Gordon Drive. This STUNNING completely remodeled 2/2 Cottage comes fully stocked with everything NEW! Located in Prestigious Olde Naples, FL. This luxurious 2 bedroom, 2 bath Cottage is just a block and a half away from the beautiful Naples white powdery-sands

  Cheri Anne DeMonico Premier Property Management

  1325 Gordon Dr, Naples, FL 34102
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  $70,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  675 2nd St S, Naples, FL 34102

  Beautiful and elegantly appointed, be the first to enjoy this 4 bedroom, 4.5 bath house in Olde Naples, just 2 blocks to the beach. The living room offers a neutral-toned l-shaped, linen couch, side chair, large TV, and fireplace. The Dining area has a rectangular table seating for 8, Walk-in Wine room; Wet Bar. The well- equipped Kitchen has all white cabinetry, white quartz counters and bar

  Marjorie Workinger Royal Shell Real Estate, Inc.

  675 2nd St S, Naples, FL 34102
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  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 2,293 Sq Ft
  • House for Rent

  320 Gulf Shore Blvd S, Naples, FL 34102

  ***DOWNTOWN***OLDE NAPLES***BEACH IS JUST A FEW STEPS FROM FRONT DOOR***4 BEDS/ 3 BATHS***FURNISHED SEASONAL***Stately charm and Olde Naples elegance await you in beautiful Villa Rosa, a classic Bahamian villa just steps from the sugar-sand beaches in Olde Naples. Four bedrooms and three full baths make this home the perfect spot for the whole family to enjoy! There's a large kitchen and living

  Angela Muscato Premier Property Management

  320 Gulf Shore Blvd S, Naples, FL 34102
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  $22,000 per month

  • 3 Beds
  • 3 Baths
  • 2,051 Sq Ft
  • House for Rent

  740 5th Ave N, Naples, FL 34102

  Soak up the sun in this pet friendly cottage! This single family pool home gives you the perfect place to drop your bags and hit the beaches that line the Gulf of Mexico, go shopping or dining at the world famous 5th Ave Naples, or relax poolside in the privacy of your own backyard. The spacious pool deck offers a covered sitting/dining area, grill station, and mini fridge. Located right around

  Stacey Cotter John R Wood Properties

  740 5th Ave N, Naples, FL 34102
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  $49,500 per month

  • 6 Beds
  • 5.5 Baths
  • 3,811 Sq Ft
  • House for Rent

  362 2nd Ave N, Naples, FL 34102

  A welcoming Olde Naples retreat awaits at Neapolitan Sky! The stately Key West style home sits amidst lush landscaping on one of the prettiest tree-lined avenues in town, just a third of a mile from beach access. Approach the home from the circular driveway and enter across the the covered front porch. The main floor has an open white marble kitchen, dining area, living room, home office with

  Stacey Cotter John R Wood Properties

  362 2nd Ave N, Naples, FL 34102
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  /13

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  120 6th St N, Naples, FL 34102

  Old Naples and easy walking distance to beach, school, shopping, etc. Charming beach cottage 3 bedrooms and 2 baths, glass enclosed den. Home did not get flooded in Ian. Terrazzo marble floors throughout. Kitchen updated with granite, some newer appliances, updated cabinets. Baths with granite and updated vanities, fixtures. Some impact windows and storm protection, laundry area with washer &

  Burkhard Klein Klein and Associates Realty In

  120 6th St N, Naples, FL 34102

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