$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
94
Old Naples Houses for Rent with Pool
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Explore Old Naples
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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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$19,995 per month
- 4 Beds
- 3 Baths
- 2,122 Sq Ft
- House for Rent
339 4th Ave N, Naples, FL 34102
339 4th Ave N, Naples, FL 34102Rare opportunity to secure your long term rental in Old Naples! Only 1.5 blocks to the beach and 9 blocks to 5th Ave S! This renovated, well maintained 4/3 beach house has soaring ceilings and a backyard oasis that dreams are made of. Offered turn key furnished. Have peace of mind knowing this house has never flooded.
Daniel Riess Compass Florida 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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$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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$43,500 per month
- 4 Beds
- 4 Baths
- 2,700 Sq Ft
- House for Rent
369 2nd Ave N, Naples, FL 34102
369 2nd Ave N, Naples, FL 34102Listed rate is for High Season (November-April). Longer High Season leases have greater discounted rates. Annual Rate is $32,625 / month. Located just three blocks from the Gulf, this charming residence offers the perfect blend of elegance, comfort, and coastal living. Nestled on the property is a sun-drenched main residence featuring open-concept interiors with vaulted ceilings and a cozy
Bill Earls John R Wood Properties
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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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$17,500 per month
- 4 Beds
- 4 Baths
- 3,641 Sq Ft
- House for Rent
258 9th Ave S, Naples, FL 34102
258 9th Ave S, Naples, FL 34102A rare opportunity to enjoy the trifecta of perfect location with this Single Family Home in Old Naples that places you within walking distance to everything Naples is famous for: 5th Avenue S, 3rd Street S and it's white-sand beaches. This property features 4 bedrooms, 4 bathrooms, a large, open floor plan with over 3600 SQFT, and it's own private pool and spa. Entertain family and friends with
Ryan Gaumer William Raveis Real Estate
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$54,995 per month
- 4 Beds
- 3.5 Baths
- 2,930 Sq Ft
- House for Rent
420 Palm Cir E, Naples, FL 34102
420 Palm Cir E, Naples, FL 34102Beautifully renovated and professionally furnished Old Naples Home steps to the Beach! This meticulously renovated and outfitted luxury rental is situated on a private, oversized corner lot. Renovations and furnishings include wide plank flooring, full kitchen remodel, Restoration Hardware and Arhaus furniture, brand new plush pillow top mattresses with fine linens and bedding. This property is
Daniel Riess Compass Florida LLC
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$47,250 per month
- 4 Beds
- 3.5 Baths
- 3,562 Sq Ft
- House for Rent
688 3rd St N, Naples, FL 34102
688 3rd St N, Naples, FL 34102ANNUAL RATE IS $35,438 / month. Listed rate is for High Season (December through April). Longer leases have greater discounted rates. See rental rate sheet. Now available is the renowned featured cover home of Home & Design magazine’s 2015 Design Issue—an architecturally significant coastal retreat just three blocks from the beach. Masterfully designed with a sleek, transitional aesthetic, this
Bill Earls John R Wood Properties
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$39,000 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 34102Welcome 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 primary suite is located on the ground level and features a
Joe Hoopfer Premier Sotheby's Int'l Realty
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$36,000 per month
- 3 Beds
- 3.5 Baths
- 2,369 Sq Ft
- House for Rent
374 14th Ave S, Naples, FL 34102
374 14th Ave S, Naples, FL 34102Key West style waterfront beach house in Aqualane Shores with direct gulf access with private boat dock and lift. Bring your boat and jet skis or paddle with kayaks or paddleboards. Beautiful 3 bedroom, 3 1/2 bath home on the water with direct gulf access with boat dock and lift. Less than a block to 3rd St restaurants and shops. 3 blocks to beach. Huge outdoor area with resort style pool, full
James Kux Downing Frye Realty Inc.
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$45,000 per month
- 3 Beds
- 3.5 Baths
- 3,558 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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$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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$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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$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 34102OPEN 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.
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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 34102SUMMER 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.
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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
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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$71,600 per month
- 5 Beds
- 6 Baths
- 5,849 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressThis 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
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$51,600 per month
- 5 Beds
- 3 Baths
- 3,585 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressLook 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 features
Tom Puckett IV Luxury Real Estate LLC
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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
613 14th Ave S, Naples, FL 34102The 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
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$55,600 per month
- 5 Beds
- 6 Baths
- 4,687 Sq Ft
- House for Rent
210 Central Ave, Naples, FL 34102
210 Central Ave, Naples, FL 34102Welcome 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
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$55,600 per month
- 6 Beds
- 7.5 Baths
- 5,900 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressThis 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
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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
605 6th Ave N, Naples, FL 34102Welcome 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 floors,
Tom Puckett IV Luxury Real Estate LLC
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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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$50,000 per month
- 4 Beds
- 3 Baths
- 3,577 Sq Ft
- House for Rent
Unlisted Address
Unlisted AddressThis 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
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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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$40,000 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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$40,000 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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