Old Naples Houses for Rent

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  $75,000 per month

  • 5 Beds
  • 5.5 Baths
  • 2,861 Sq Ft
  • House for Rent

  287 11th Ave S, Naples, FL 34102

  Newly restored + luxuriously to the NTH Degree. Absolutely everything you dream about in a Naples vacation rental is contained within the walls of the updated Old Glory Cottage and Guesthouse located in the Olde Naples historic district (renovated in 2011 by the Williams Group/Kristen Williams). Walk to the beach (yes, 2.5 blocks). Walk to 3rd Street and 5th Avenue restaurants and shopping. 287

  Michelle Craft Naples Homes and Rentals Inc

  287 11th Ave S, Naples, FL 34102
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  $13,000 per month

  • 3 Beds
  • 4 Baths
  • 2,064 Sq Ft
  • House for Rent

  201 8th St S Unit 104, Naples, FL 34102

  RENTED Jan-March 2026 | Available April 2026 at $13,000 | Available Sept-Dec at $9,500 | Available Long-Term | Welcome to the ultimate vacation escape, at the prestigious Mark on 8th, where luxury and convenience meet. This downtown fully furnished coastal contemporary condo offers a thoughtfully designed modern living space while boasting three beautifully appointed bedrooms and four elegant

  Patrick Burke Jr Halo Home Management LLC

  201 8th St S Unit 104, Naples, FL 34102
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  /26

  $55,600 per month

  • 5 Beds
  • 5 Baths
  • 4,251 Sq Ft
  • House for Rent

  Unlisted Address

  This finely decorated home is the pinnacle of luxury Old Naples living. The Balmoral has five bedrooms and plenty of living space, with tall ceilings and large windows for tons of light. The open living room and kitchen layout overlooks sliding glass doors that lead directly to the pool. The pool area itself features a large electric pergola for when you want to get out of the sun, and a fully

  Tom Puckett IV Luxury Real Estate LLC

  Unlisted Address
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  $5,688 per month

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • House for Rent

  550 3rd Ave N, Naples, FL 34102

  ***NAPLES BEACH GET-AWAY***UNIQUE OLDE NAPLES LIVING*** 4 BLOCKS FROM THE BEACH!!!! HEART OF OLDE NAPLES, FAMOUS 5TH AVENUE SHOPPING AND RESTAURNT GALORE!!! Searching for your own affordable piece of paradise in the heart of Downtown Naples? Look no further than this rental! You'll enjoy a convenient location that's a five-minute stroll to the beach and downtown fifth avenue where high-end dining

  Angela Muscato Premier Property Management

  550 3rd Ave N, Naples, FL 34102
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  $26,500 per month

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

  590 E Lake Dr, Naples, FL 34102

  OPEN FOR 2025-2026 SEASON!! LAKE VIEWS! Enjoy Olde Naples at its best! Wonderful 4 bedroom, 3 bath, pool/spa home, sits on a quiet lake just off 5th Avenue South. Walk to fine restaurants, shops and galleries plus 4 blocks to Naples' white, sandy beaches! There are two master bedrooms, one upstairs, with a private deck overlooking the lake, and one downstairs, with direct access to the pool area,

  Marjorie Workinger Royal Shell Real Estate, Inc.

  590 E Lake Dr, Naples, FL 34102
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  $40,000 per month

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft
  • House for Rent

  1375 Gordon Dr, Naples, FL 34102

  HISTORIC OLD NAPLES. This recently remodeled property on Gordon Drive near 3rd Street South has a Cottage with 3 sleeping rooms and a one-bedroom cabana joined by a large wood-deck with multiple seatings areas for outdoor dining, conversation or taking in the afternoon sun. The Cabana is for a party of two and includes a bedroom with a king bed, a full bath with a walk-in shower, a morning

  Julie Baron Premier Sotheby's Int'l Realty

  1375 Gordon Dr, Naples, FL 34102
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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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  $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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  $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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  $6,000 per month

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

  850 Central Ave Unit 311, Naples, FL 34102

  Available Annually ($6,000/M) and Seasonally ($13,000/M). Emphasizing the significance of location, this exquisite 2-bedroom, 2-full bathroom luxury condominium serves as an ideal year-round 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

  Sarah Wayne Gulf Coast International Lux R

  850 Central Ave Unit 311, 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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  $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 IV Luxury Real Estate LLC

  Unlisted Address
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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 IV 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 IV Luxury Real Estate LLC

  613 14th Ave S, Naples, FL 34102
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  /19

  $55,600 per month

  • 5 Beds
  • 6 Baths
  • 4,687 Sq Ft
  • House for Rent

  210 Central Ave, Naples, FL 34102

  Welcome to your own slice of paradise in Naples, Florida. Nestled in a prime location, just 5 blocks away from the vibrant 5th Avenue shops and restaurants, and a mere 2 blocks from the sun-kissed beach, this opulent 3-story estate is a dream come true. With 5 spacious bedrooms, this residence exudes elegance and sophistication. The convenience of a private elevator ensures accessibility to every

  Tom Puckett IV Luxury Real Estate LLC

  210 Central Ave, 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 IV Luxury Real Estate LLC

  Unlisted Address
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  /16

  $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 IV Luxury Real Estate LLC

  605 6th Ave N, Naples, FL 34102
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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 IV Luxury Real Estate LLC

  85 13th Ave 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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  $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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  $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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  $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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  /27

  $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 IV Luxury Real Estate LLC

  Unlisted Address
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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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  $30,000 per month

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

  370 6th Ave S, Naples, FL 34102

  Now available January 2026 at $30,000 plus taxes and fees due to cancelation. 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

  Michael Dedio Naples Trust Real Estate Servi

  370 6th Ave S, Naples, FL 34102
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  $40,000 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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  /16

  $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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  /19

  $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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  /23

  $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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  /25

  $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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