$48,000 per month
- 5 Beds
- 3.5 Baths
- 3,277 Sq Ft
- House for Rent
687 9th Ave S, Naples, FL 34102
687 9th Ave S, Naples, FL 34102
73
Old Naples Houses for Rent with Pool
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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
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
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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
287 11th Ave S, Naples, FL 34102Newly 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
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$5,500 per month
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- House for Rent
778 5th Ave N, Naples, FL 34102
778 5th Ave N, Naples, FL 34102Available NOW for Annual, Monthly, & Weekly Rentals!Hop on over to Sky Blue Cottage. Your tropical hideout in the heart of Naples where it's always blue skies ahead! This quaint 3 bedroom / 2 bathroom Olde Naples house is just a 15 minute walk to anything and everything you need! Be it the beach, shopping & dining on 5th Avenue, or groceries from Wynn's Market for dining 'al fresco' in
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$55,600 per month
- 5 Beds
- 5 Baths
- 4,251 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressThis 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
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$5,500 per month
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- House for Rent
465 8th St N, Naples, FL 34102
465 8th St N, Naples, FL 34102Fully furnished home! Available for Annual, Monthly, & Weekly Rentals.AVAILABLE NOW & Beyond! Weekly/Monthly/Yearly Rentals! 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
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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
590 E Lake Dr, Naples, FL 34102Enjoy 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, both offering a king-size bed, and
Marjorie Workinger Royal Shell Real Estate, Inc.
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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
1375 Gordon Dr, Naples, FL 34102HISTORIC 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
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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
56 Gulf Shore Blvd S, Naples, FL 34102Magnificent 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 home is furnished with clean
Marjorie Workinger Royal Shell Real Estate, Inc.
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$45,000 per month
- 3 Beds
- 4.5 Baths
- 3,394 Sq Ft
- House for Rent
678 11th Ave S, Naples, FL 34102
678 11th Ave S, Naples, FL 34102OPEN 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.
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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
85 13th Ave S, Naples, FL 34102Never 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
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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
361 1st Ave N, Naples, FL 34102This 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.
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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
255 2nd Ave N, Naples, FL 34102Discover 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
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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
67 8th Ave S, Naples, FL 34102Available 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
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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
67 8th Ave S, Naples, FL 34102Available 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
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$100,000 per month
- 4 Beds
- 5.5 Baths
- 4,381 Sq Ft
- House for Rent
1230 Gulf Shore Blvd S, Naples, FL 34102
1230 Gulf Shore Blvd S, Naples, FL 34102Located in the sought-after beach block of Old Naples, this gorgeous home features western exposure and is just a short stroll from the iconic Naples Pier, charming boutiques, and exquisite dining on Third Street South. This remarkable home has stood resilient through the last three major hurricanes—Hurricane Ian, Hurricane Milton, and Hurricane Helene—sustaining zero damage during these intense
Austin Kellam Coldwell Banker Realty
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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
300 2nd Ave N, Naples, FL 34102BOOKED 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.
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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
359 2nd Ave N, Naples, FL 34102BOOKED 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.
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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
680 8th Ave S, Naples, FL 34102Annual 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
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$30,000 per month
- 3 Beds
- 3 Baths
- 2,776 Sq Ft
- House for Rent
444 2nd Ave N, Naples, FL 34102
444 2nd Ave N, Naples, FL 34102Discover 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
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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
370 6th Ave S, Naples, FL 34102Nestled 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
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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
12 6th St S, Naples, FL 34102Welcome 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
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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
380 5th Ave N, Naples, FL 34102Experience 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
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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
380 5th Ave N, Naples, FL 34102Experience 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
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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
271 1st Ave S, Naples, FL 34102Annual 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
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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
431 1st Ave N, Naples, FL 34102Annual 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
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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
195 2nd Ave N, Naples, FL 34102Annual Rate is $26,250 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
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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
206 1st Ave N, Naples, FL 34102Annual 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
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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
354 1st Ave N, Naples, FL 34102Annual 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
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$54,000 per month
- 5 Beds
- 6.5 Baths
- 5,641 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressAnnual 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
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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
168 2nd Ave N, Naples, FL 34102Annual 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
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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
194 4th Ave N, Naples, FL 34102The annual rate is $27,750 / 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 floors,
Bill Earls John R Wood Properties
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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
434 3rd Ave S, Naples, FL 34102Arguably 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
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$70,000 per month
- 5 Beds
- 5.5 Baths
- 5,145 Sq Ft
- House for Rent
154 4th Ave N, Naples, FL 34102
154 4th Ave N, Naples, FL 34102Coastal 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
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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
860 7th St S, Naples, FL 34102Quintessential 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
Joe Hoopfer Premier Sotheby's Int'l Realty
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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
675 2nd St S, Naples, FL 34102Beautiful 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.
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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
740 5th Ave N, Naples, FL 34102Soak 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
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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
362 2nd Ave N, Naples, FL 34102A 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
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$45,000 per month
- 3 Beds
- 3.5 Baths
- 2,567 Sq Ft
- House for Rent
500 3rd Ave N, Naples, FL 34102
500 3rd Ave N, Naples, FL 341025 BLOCKS FROM THE BEACH. Inquire about Weekly Specials. Welcome to "Naples Walk" Located just 4 short blocks from the beach, this thoughtfully designed home features a great room concept with three bedrooms and four bathrooms. The large kitchen and great room open to a generous outside living area that includes an impressive pool and spa, summer kitchen, and outdoor fireplace. The large master
Joe Hoopfer Premier Sotheby's Int'l Realty
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$45,000 per month
- 3 Beds
- 3.5 Baths
- 3,515 Sq Ft
- House for Rent
160 3rd St N, Naples, FL 34102
160 3rd St N, Naples, FL 34102Experience the ultimate in luxury living in this stunning residence located in prestigious Olde Naples, just steps away from the white sugar sand beaches of the Gulf of Mexico. Recently renovated to reflect today's lifestyle, this Key West architectural gem boasts over 3,600 square feet of interior living space with three bedrooms, an office, and three and a half bathrooms.As you step through
Monica Simon William Raveis Real Estate
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