Old Naples Homes for Rent

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  $87,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,800 Sq Ft
  • House for Rent

  56 Gulf Shore Blvd S, Naples, FL 34102

  SUMMER AND FALL 2025 OPEN!!! Magnificent Beachfront home located in Olde Naples. This Four Bedroom, Four Bath home with a one Bedroom/one Bath/Living Room/Kitchen "Guest House", has been newly constructed in 2001. Each bedroom gives one the feeling of a private suite. It's simplicity of design and the way the home merges with the beach offers one a calmness when you walk in. This contemporary

  Marjorie Workinger Royal Shell Real Estate, Inc.

  56 Gulf Shore Blvd S, Naples, FL 34102
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  $25,000 per month

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  XXXX Eleventh Ave S, Naples, FL 34102

  Life at the Beach! OPEN FOR 2025- 2026 Season! Completely gutted and remodeled! All New Decor!This Key West style cottage has been totally renovated and redecorated after Hurricane Ian. A Prime location, and just 60 steps to one of Florida’s prettiest beaches! The vibrant and historic Third Street District, with its' many shops and restaurants, is just 3 blocks away. This charming home

  Marjorie Workinger Royal Shell Real Estate, Inc.

  XXXX Eleventh Ave S, Naples, FL 34102
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  $13,000 per month

  • 2 Beds
  • 2 Baths
  • 1,209 Sq Ft
  • House for Rent

  850 Central Ave Unit 311, Naples, FL 34102

  Available Seasonally ($13,000/M) and Annually ($6,000/M). Emphasizing the significance of location, this exquisite 2-bedroom, 2-full bathroom luxury condominium serves as an ideal winter retreat. Exuding contemporary vibes, this residence includes a gourmet kitchen with a spacious breakfast bar, a natural gas stove, Sub-zero appliances, a wine cooler, and quartz countertops. The primary suite,

  Sarah Wayne Gulf Coast International Lux R

  850 Central Ave Unit 311, Naples, FL 34102
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  $45,000 per month

  • 4 Beds
  • 4 Baths
  • 3,394 Sq Ft
  • House for Rent

  678 11th Ave S, Naples, FL 34102

  OPEN FOR 2025-26’’ SEASON! FRESHLY REMODELED this summer, this 4+ Bedroom/ Den/4.5 bath, bayfront house is nestled between the Gulf of Mexico and Naples Bay, less than one mile to the beach, Third Street, and Fifth Avenue restaurants, shops, and galleries. This residence offers an open floor-plan, 4 bedrooms, a Den/Office area; 4.5 baths, 3 car garage, and a beautiful outdoor pool area with a

  Marjorie Workinger Royal Shell Real Estate, Inc.

  678 11th Ave S, Naples, FL 34102
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  $71,600 per month

  • 5 Beds
  • 6 Baths
  • 5,849 Sq Ft
  • House for Rent

  Unlisted Address

  This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Wonderful & well-built in 2007! Open & bright, loaded w/upgrades! Absolutely ideal location in the heart of Olde Naples just 5 doors to the

  Tom Puckett Luxury Real Estate LLC

  Unlisted Address
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  $60,000 per month

  • 4 Beds
  • 4.5 Baths
  • 4,110 Sq Ft
  • House for Rent

  613 14th Ave S, Naples, FL 34102

  The Coconut Plantation is the pinnacle of Naples luxury living. Prepared to be enchanted upon arrival as you are greeted by a lush landscape. Royal Poinciana frame this sprawling plantation style house that overflows with southern charm. A brick paver circular driveway provides the gateway to this southern style living with amenities and luxury appointments that would please many fields of

  Tom Puckett Luxury Real Estate LLC

  613 14th Ave S, Naples, FL 34102
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  $51,600 per month

  • 5 Beds
  • 3 Baths
  • 3,585 Sq Ft
  • House for Rent

  Unlisted Address

  Look out your window to see a stunning view of the Gulf, have breakfast, enjoy the beach or a stroll down the Naples Pier. The Pier at night is amazing--enjoy a 360 degree view of the ocean under the stars or come home to relax on the rooftop deck and enjoy the night sky.The Pier House is stunning home and the location is even better. This home has 5 bedrooms and 3 baths. The Main House

  Tom Puckett Luxury Real Estate LLC

  Unlisted Address
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  $5,000 per month

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft
  • Condo for Rent

  421 12th Ave S Unit 11, Naples, FL 34102

  Experience the perfect blend of lifestyle, location, and convenience at this hidden gem in the vibrant heart of downtown Naples at the intersection just a block away from the hub of 3rd St South Shopping District. Step into a well-designed space featuring an updated kitchen with granite countertops and diagonal tile flooring throughout, creating a seamless flow of natural light and providing

  Rob Mauceli Compass Florida LLC

  421 12th Ave S Unit 11, Naples, FL 34102
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  $55,600 per month

  • 6 Beds
  • 7.5 Baths
  • 5,900 Sq Ft
  • House for Rent

  Unlisted Address

  This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Open & bright, loaded w/upgrades! Absolutely ideal location in the heart of Olde Naples just 5 doors to the beach Luxurious ground floor master

  Tom Puckett Luxury Real Estate LLC

  Unlisted Address
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  $59,600 per month

  • 4 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • House for Rent

  85 13th Ave S, Naples, FL 34102

  Never miss a sunset from this beautifully appointed beach house, located just steps from Naples Famous Pier and beautiful white sand beaches, this home's location can't be beat! A luxurious luxury home with all the bells and whistles. Enjoy sunsets from the rooftop deck or stroll down to the beautiful beach and watch the dolphins frolic in the waves. This 4 bedroom home has enough room for your

  Tom Puckett Luxury Real Estate LLC

  85 13th Ave S, Naples, FL 34102
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  $31,600 per month

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  605 6th Ave N, Naples, FL 34102

  Welcome to the Cypress House!Professionally decorated 3 bedroom and 2.5 bathroom home in the heart of Old Naples. The Cypress is on a quiet mahogany tree-lined street just a short walk to the beautiful beaches and refreshing waters of the Gulf of Mexico as well as popular dining, shopping, and the nightlife of Fifth Ave South. The Cypress features spacious living areas, beautiful tiled

  Tom Puckett Luxury Real Estate LLC

  605 6th Ave N, Naples, FL 34102
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  $30,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,700 Sq Ft
  • Condo for Rent

  476 1st Ave N, Naples, FL 34102

  Nestled in the heart of Olde Naples, this lovely, 4 bedroom, 3.5 bath residence offers comfort, privacy, and location. As you enter the house, you are greeted with a spacious and open floor- plan, offering a cheerful interior. The living room offers a comfortable, upholstered couch, 3 side chairs, fireplace, and beautiful artwork.The dining area offers a mahogany, rectangular table, with

  Marjorie Workinger Royal Shell Real Estate, Inc.

  476 1st Ave N, Naples, FL 34102
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  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 902 Sq Ft
  • Condo for Rent

  101 8th St S, Naples, FL 34102

  Experience the best of Olde Naples in this beautifully appointed, turnkey 2-bedroom, 2-bathroom condo at SoCe Flats. Available for both weekly or monthly rentals, this residence offers a fully equipped kitchen, washer/dryer, and a private balcony off the great room, providing a perfect spot to unwind and enjoy the Naples lifestyle.Inside, you’ll find luxurious Clive Daniel Home

  Lauren Trethewey Realty One Group MVP

  101 8th St S, Naples, FL 34102
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  $16,000 per month

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • House for Rent

  361 1st Ave N, Naples, FL 34102

  This charming cottage offers 3 bedroomss,3 bath and is nestled in Olde Naples, on a quiet street, lined with beautiful trees, just 3.5 blocks to Naples' pristine, white sandy beaches, and magnificent sunsets. The living room is decorated in cream couch/loveseat with blue trim, and chair. The family room is decorated with bright cheerful colors of yellow, orange, etc. for the couches, floral

  Marjorie Workinger Royal Shell Real Estate, Inc.

  361 1st Ave N, Naples, FL 34102
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  $13,500 per month

  • 2 Beds
  • 2 Baths
  • 1,522 Sq Ft
  • Condo for Rent

  820 3rd St S Unit 101, Naples, FL 34102

  WALKING DISTANCE TO BEACH, 5TH AVE AND 3RD ST S!!! This 2-bedroom + den, 2-bath ground-floor condo is perfectly located in the heart of Olde Naples, just 2.5 blocks from the stunning 8th Avenue beach. You’ll love the convenience of being just 3 blocks from 5th Avenue South and the 3rd Street South shopping and dining districts. With this prime location, you’re truly within walking distance of

  Monica Simon William Raveis Real Estate

  820 3rd St S Unit 101, Naples, FL 34102
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  $35,000 per month

  • 3 Beds
  • 4 Baths
  • 3,220 Sq Ft
  • House for Rent

  433 5th St S, Naples, FL 34102

  Experience the ultimate Old Naples lifestyle in this luxurious private villa, perfectly located less than a block from the iconic 5th Ave South. This stunning three-story home offers 3 bedrooms, 4 full baths, a private pool, spa, and elevator for unparalleled comfort and convenience. On the first floor, you’ll find a bedroom with two full-size beds, a full bath, and a wet bar, all easily

  Sarah Wayne Gulf Coast International Lux R

  433 5th St S, Naples, FL 34102
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  $12,000 per month

  • 4 Beds
  • 3 Baths
  • 2,349 Sq Ft
  • House for Rent

  299 1st Ave S, Naples, FL 34102

  !!AVAILABLE NOW!! Annual, Monthly, Weekly Rentals!Olde Naples, wonderful 3BDRM Office w/sofa bed used as 4th bedroom/3 BATH ranch home. Just 3 blocks to the beach and 5 blocks to 5th Avenue!Video Tour Here: youtu.be/yvtanc8xu5kGranite Kitchen and open floor plan. 40' Lap pool with spa in a beautiful secluded tropical yard. Living room, dining room, laundry room, screened

  299 1st Ave S, Naples, FL 34102
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  $43,500 per month

  • 6 Beds
  • 6.5 Baths
  • 4,351 Sq Ft
  • House for Rent

  255 2nd Ave N, Naples, FL 34102

  Discover the ultimate family beach retreat, located just seven doors from the pristine white sands of Old Naples! Perfectly designed for multi-generational gatherings or groups of friends, this unique property features two beautifully updated homes—the main house and a guest house—each offering modern comforts with a touch of historic charm. Recently renovated, both homes are connected by a

  Monica Simon William Raveis Real Estate

  255 2nd Ave N, Naples, FL 34102
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  $75,000 per month

  • 4 Beds
  • 3 Baths
  • 3,500 Sq Ft
  • House for Rent

  67 8th Ave S, Naples, FL 34102

  Available Weekly beginning May 1,2025. Welcome to the Kite House a one of a kind Old Naples family compound only steps to The Gulf of Mexico. This fabulous new Naples Beach Retreat is comprised of three residences sleeping up to 16 people. There are 3 residences comprised of a 3 bedroom, 2 bedroom and one bedroom cottage. The 2 bedroom residence can be rented separately. From the front porches,

  Monica Simon William Raveis Real Estate

  67 8th Ave S, Naples, FL 34102
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  $75,000 per month

  • 4 Beds
  • 3 Baths
  • 3,500 Sq Ft
  • House for Rent

  67 8th Ave S, Naples, FL 34102

  Available Weekly beginning May 1,2025. Welcome to the Kite House a one of a kind Old Naples family compound only steps to The Gulf of Mexico. This fabulous new Naples Beach Retreat is comprised of three residences sleeping up to 16 people. There are 3 residences comprised of a 3 bedroom, 2 bedroom and one bedroom cottage. The 2 bedroom residence can be rented separately. From the front porches,

  Monica Simon William Raveis Real Estate

  67 8th Ave S, Naples, FL 34102
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  $6,200 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  465 8th St N, Naples, FL 34102

  Fully furnished home! Available furnished or unfurnished for Annual, Monthly, & Weekly Rentals. AVAILABLE NOW & Beyond! Call Kate for more info!Be transported back in time to the beachy town days of Olde Naples with the modern comforts of today in this charming newly renovated beach cottage. Located in the heart of Olde Naples, 1 block west of 41, be shopping & dining on 5th Avenue or at

  465 8th St N, Naples, FL 34102
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  $42,900 per month

  • 2 Beds
  • 2 Baths
  • 2,500 Sq Ft
  • House for Rent

  47 8th Ave S, Naples, FL 34102

  Weekly Rentals Available Starting May 1, 2025 – Plan Your Beach Vacation Now!Welcome to the “Kite House,” a charming Old Naples retreat just steps from the Gulf of Mexico. This listing features the beautifully designed 2-bedroom, 2-bath residence, perfect for a family getaway or a relaxing couples’ retreat. Enjoy all the comforts of a newly remodeled property, complete with exquisite decor,

  Monica Simon William Raveis Real Estate

  47 8th Ave S, Naples, FL 34102
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  $42,900 per month

  • 2 Beds
  • 2 Baths
  • 2,500 Sq Ft
  • House for Rent

  47 8th Ave S, Naples, FL 34102

  Weekly Rentals Available Starting May 1, 2025 – Plan Your Beach Vacation Now!Welcome to the “Kite House,” a charming Old Naples retreat just steps from the Gulf of Mexico. This listing features the beautifully designed 2-bedroom, 2-bath residence, perfect for a family getaway or a relaxing couples’ retreat. Enjoy all the comforts of a newly remodeled property, complete with exquisite decor,

  Monica Simon William Raveis Real Estate

  47 8th Ave S, Naples, FL 34102
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  $50,000 per month

  • 4 Beds
  • 3 Baths
  • 3,577 Sq Ft
  • House for Rent

  Unlisted Address

  This newly renovated home is centrally located to the best Old Naples has to offer. One block from the beach, and a short walk to Fifth Avenue's luxurious restaurants and shops. The house has an open floor plan concept, with a connected family room, dining room, and kitchen, along with a den and an office.

  Tom Puckett Luxury Real Estate LLC

  Unlisted Address
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  $9,900 per month

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft
  • House for Rent

  282 4th St S Unit 204, Naples, FL 34102

  DOWNTOWN NAPLES, CLOSE TO 5TH AVENUE - 3 MINUTES TO THE BEACHES Welcome to our Beautiful Beach Breeze Condo, which is located on a quiet street in downtown Naples. LOCATION, LOCATION, LOCATION! This vacation rental offers 1058 Square Feet of newly remodeled living space and the perfect location - Only two blocks away from Downtown 5th Avenue and four short blocks to the beach! Naples 5th Avenue

  Dali Mihajlovic All In Property Management LLC

  282 4th St S Unit 204, Naples, FL 34102
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  $24,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,704 Sq Ft
  • Condo for Rent

  201 8th St S Unit 209, Naples, FL 34102

  Indulge in the ultimate luxury and convenience at The Mark on 8th, a premier condominium community in the heart of Olde Naples. Just steps from world-class boutiques, charming cafes, acclaimed restaurants, and the pristine sandy beaches of the Gulf of Mexico, this prime location offers everything you need for an unforgettable Southwest Florida vacation. Unit 209 is thoughtfully designed to

  Stacey Cotter John R Wood Properties

  201 8th St S Unit 209, Naples, FL 34102
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  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 979 Sq Ft
  • Condo for Rent

  284 4th St S Unit 103, Naples, FL 34102

  The envy of location! Tucked into the heart of Olde Naples just two blocks from 5th Ave S and four blocks from the sugar white sand beach, Beach Breeze offers the opportunity to live in one of the most desirable residential neighborhoods in the USA. Unit 284 offers the convenience of a ground floor entry and has wonderful views out to tree-lined 4th St S from newer impact resistant windows.

  Stacey Cotter John R Wood Properties

  284 4th St S Unit 103, Naples, FL 34102
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  $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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  $30,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,704 Sq Ft
  • Condo for Rent

  201 8th St S Unit 311, Naples, FL 34102

  Indulge in the pinnacle of luxury and convenience at The Mark on 8th, a premier condominium development nestled in the heart of Olde Naples. Just a short walk from boutiques, quaint cafes, acclaimed restaurants, and the pristine beaches along the Gulf of Mexico, this exceptional location is ideal for a Southwest Florida getaway. Unit 311 is meticulously designed to accommodate larger groups. The

  Stacey Cotter John R Wood Properties

  201 8th St S Unit 311, Naples, FL 34102
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  $3,250 per month

  • 2 Beds
  • 1 Bath
  • 755 Sq Ft
  • Condo for Rent

  473 12th Ave S Unit B-10, Naples, FL 34102

  Dates available 11/15/2025-12/31/2025 and all April 2026- December 2026. 30 day minimum. Book early the peak season lease 12 months in advance (2026 peak jan-mar gone). Located in the heart of Naples and just 1 block from the Historic 3rd Street South. You will find fine dining, boutique shops, and a weekly farmer's market. As if that wasn't enough the condo is only a few blocks from the beach

  473 12th Ave S Unit B-10, Naples, FL 34102

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