$13,000 per month
365 5th Ave S Unit 303, Naples, FL 34102
365 5th Ave S Unit 303, Naples, FL 34102Explore Old Naples
$5,000 per month
540 4th Ave S Unit 13, Naples, FL 34102
540 4th Ave S Unit 13, Naples, FL 34102
$48,000 per month
687 9th Ave S, Naples, FL 34102
687 9th Ave S, Naples, FL 34102
$5,000 per month
473 12th Ave S Unit B-10, Naples, FL 34102
Dates available 5/1/205-12/31/2025 and all 2026. 30 day minimum. Book early the peak season lease 12 months in advance (2025 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 and Naples Pier. Bonaire
$6,700 per month
766 Central Ave Unit 117, Naples, FL 34102
Three Bedrooms |Two Bathrooms | First -Floor Condo in the Heart of Naples. This beautiful condo offers the perfect blend of comfort and convenience. Ideally located just four blocks from 5th Avenue South Naples' renowed destination for fine dining, shopping, and entertainment and only minutes away from the award winning white sandy beaches on the gulf coast. Enjoy breathtaking sunsets and
Ody Noa Hamro & Associates LLC
$5,500 per month
465 8th St N, Naples, FL 34102
Fully 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
$22,000 per month
1165 4th St S Unit 2, Naples, FL 34102
OPEN FOR 2026 Season!! Book EARLY!! OPEN FOR Summer and Fall too! This completely updated 3 bedroom/3+ bath residence offers everything one thinks of in Olde Naples: Central location, Walk to the pristine beaches, Naples' fishing pier, restaurants/shopping. This 2-story Villa sleeps six; it is spacious, well furnished, well equipped, and offers one a very comfortable place to stay in Olde Naples.
Marjorie Workinger Royal Shell Real Estate, Inc.
$2,195 - $2,295 per month
Le Bijou
2 Beds
660 8th St N, Naples, FL 34102
$55,000 per month
434 3rd Ave S, Naples, FL 34102
Arguably the best location for a rental in Olde Naples! Only 3 blocks from the white sandy beaches that make Naples one of the most desired locations in FL. This dream home boasts nearly 5,000 square feet with heated pool, southern exposure, and 4 Clive Daniel decorated bedrooms, each with its own en suite bath. One bedroom features four floating bunks, each with a privacy curtain, lamp and
Todd Culmer Waterfront Realty Group Inc
$1,795 - $2,395 per month
Villas Isabel
1 - 2 Beds
618-628 8th St N, Naples, FL 34102
$33,000 per month
425 5th St S Unit A, Naples, FL 34102
BOOKED FOR THE 2026 SEASON. Location, location, location! This stunning, 3 level, 3 bedroom villa is located less than 1 block from Fifth Avenue in beautiful downtown Naples, featuring a private pool/spa and outdoor kitchen with wet bar & fridge. As you enter the 1st level you are greeted by a spacious foyer leading to a comfortable den with a Murphy bed, large screen TV and private outdoor
Sarah Wayne Gulf Coast International Lux R
$10,000 per month
250 7th Ave S Unit 301, Naples, FL 34102
*Jan - Mar 2026 Rented. Available Off-Peak Months. Welcome to The Olde Towne Condominium, your perfectly located vacation home in the heart of Olde Naples. This fully renovated unit offers 2 bedrooms and 2 full bathrooms. Outstanding features include an open-concept gourmet kitchen, top-quality stainless-steel appliances, washer-dryer, new bathrooms, plantation shutters and more! The primary
Kal Anderson Coldwell Banker Realty
$10,000 per month
250 7th Ave S Unit 202, Naples, FL 34102
*Jan - Mar 2026 Rented. Available Off-Peak Months. Welcome to The Olde Towne Condominium, your perfectly located vacation home in the heart of Olde Naples. This fully renovated unit offers 2 bedrooms and 2 full bathrooms. Outstanding features include an open-concept gourmet kitchen, top-quality stainless-steel appliances, washer-dryer, new bathrooms, plantation shutters and more! The primary
Kal Anderson Coldwell Banker Realty
$55,000 per month
642 6th Ave N, Naples, FL 34102
Escape to this stunning Olde Naples retreat, perfectly located on a beautiful tree-lined street just blocks from the beach, parks, and the vibrant dining and shopping of Fifth Avenue South and Third Street. Designed for both relaxation and entertaining, this spacious single-level home offers nearly 4,000 sq. ft. of living space with 5 bedrooms, multiple living areas, and a flexible layout ideal
Monica Simon William Raveis Real Estate
$14,000 per month
376 3rd St S Unit 102, Naples, FL 34102
Discover the best of Olde Naples living in this beautifully decorated 2-bedroom, 2-bath condo, ideally located just one block from the bustling 5th Ave S. Enjoy easy access to an incredible array of top-rated restaurants, boutique shopping, vibrant nightlife, and charming art galleries — all within walking distance. The pristine white sand beach is only three blocks away, perfect for sunbathing,
Monica Simon William Raveis Real Estate
$5,000 per month
546 Broad Ave S Unit 546, Naples, FL 34102
Available 1/3/26 - 4/3/26. This second-floor walk-up is located in Olde Naples, 2 blocks from the shopping and dining district that is 3rd Avenue South. This unit is approximately a 1/2 mile walk to the beach and the Naples Pier. Building does have common laundry facilities located on the first floor that was recently renovated. The Village Green community amenities are located just across
Kathy Packish ERA Naples Realty Services
$35,000 per month
860 7th St S, Naples, FL 34102
Quintessential Olde Naples charm. Lovely, updated, pet-friendly, pool home, perfect for a luxurious vacation rentla. The new pool was just poured in early Fall 2020, and the entire outfoor 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.
Joe Hoopfer Premier Sotheby's Int'l Realty
$28,000 per month
223 11th Ave S, Naples, FL 34102
Olde Naples Oasis is a short walk to the beautiful Gulf of Mexico! Nestled in a non-gated coastal neighborhood, this 2-story home with a Key West ambiance is the ideal place to relax & unwind enjoying the Florida sun. Situated right next to Naples 5th Ave AND 3rd Street South where you can find world-famous shopping & dining, plus a 2-block walk or bike ride to the gorgeous beach that lines the
Stacey Cotter John R Wood Properties
$6,250 per month
766 Central Ave Unit 304, Naples, FL 34102
Live steps from everything you love about Olde Naples in this 2 bed, 2 bath updated condo at Central Gardens. Tucked into a lush, low-density community with a sparkling pool, this Central Gardens condo is just a short walk to vibrant 5th Avenue South, the sun-soaked Gulf beaches, and Wynn’s Market—and only minutes by car to the dining, shopping, and galleries of 3rd Street South. Inside, enjoy
Timothy Peterson Realty One Group MVP
$1,850 per month
421 12th Ave S Unit 5, Naples, FL 34102
Wonderful 1 bedroom, 1 bath, 1st floor condo. No flooding from any storm. Walking distance to pier, beach, 3rd St, 5th Ave, restaurants, shops. Active Community with pool, shuffleboard, bocci ball, library, clubhouse, events, etc. Only 18 units in building. Covered carport parking in back of condo. Impact Resistant windows throughout building. Storage in building. Paver driveway. New paint
James Kux Downing Frye Realty Inc.
$32,500 per month
477 3rd Ave S Unit 2, Naples, FL 34102
30 Day Minimum. Available November and/or December 2025 at $25,000 per month. Available January or April 2026 at $32,500 per month. Newly Available! Escape to this stunning beach villa in the heart of Olde Naples—just 4 blocks from the Gulf and 2 blocks from the world-class dining, boutique shops, and art galleries of 5th Avenue South. The perfect winter retreat awaits you!The main level
Michael Dedio Naples Trust Real Estate Servi
$150,000 per month
1270 Gulf Shore Blvd S, Naples, FL 34102
Escape to paradise in this stunning beachfront estate offering the perfect blend of coastal elegance and modern comfort. This spacious home boasts 5 bedrooms plus several flex spaces 5 and a half baths and private elevator, providing ample room for family, guests or a home office set up. Enjoy breathtaking ocean views from your private balcony, direct beach access, and the soothing sounds of the
Michelle Lauzier Douglas Elliman Florida,LLC
$6,800 per month
578 Broad Ave S Unit 578, Naples, FL 34102
Welcome to your slice of paradise in the vibrant Condo in the heart of Olde Naples! This stunningly renovated condominium is not just a place to live – it’s a lifestyle choice for those aged 55 and better, looking to enjoy the sun-drenched beauty of Florida’s Gulf Coast. Nestled in an unbeatable location, you are mere steps away from pristine beaches, upscale shopping, and delectable dining
Dawn Hardee Royal Shell Real Estate, Inc.
$6,500 per month
766 Central Ave Unit 112, Naples, FL 34102
LOCATION, LOCATION, LOCATION!!! This 2 bedroom / 2 bath unit is located in the heart of ‘Olde Naples’, featuring a king bed in the master with a trundle in the guest. Only four blocks from 5th Avenue for world class dining, shopping and nightlife. The area is historical & quaint, but offers all of the modern conveniences of theater, a cultural arts center and a library. ‘Central Garden’ provides
Maria Metzger Royal Shell Real Estate, Inc.
$12,000 per month
175 5th Ave S Unit 103, Naples, FL 34102
WINTER IN BEAUTIFUL DOWNTOWN NAPLES!!! AVAILABLE WEEKLY OR MONTHLY NOW THROUGH December 23rd, 2025; December 31, 2025 Through January 31st, 2026 AND From March 1st Through April 30th, 2026. Spend your vacation in the HEART OF NAPLES!!! Meticulously Maintained, this GROUND FLOOR Condo is beautifully COMPLETELY RENOVATED with 2 King Beds and its own washer and dryer. Fifth Avenue Beach Club offers
Louise Messina Phase III Real Estate Services
$12,000 per month
175 5th Ave S Unit 104, Naples, FL 34102
WINTER IN BEAUTIFUL DOWNTOWN NAPLES!!! AVAILABLE WEEKLY OR MONTHLY NOW THROUGH December 23rd, 2025, December 31, 2025 Through February 9th, 2026 AND From February 23rd Through April 30th,2026. Spend your vacation in the HEART OF NAPLES!!! Meticulously Maintained, this GROUND FLOOR Condo is beautifully COMPLETELY RENOVATED with 2 King Beds and its own washer and dryer. Fifth Avenue Beach Club
Louise Messina Phase III Real Estate Services
$65,000 per month
154 4th Ave N, Naples, FL 34102
Coastal Chalet in Olde Naples - this stunning coastal dream is only a 2-min walk to the sparkling coastline of the Gulf of Mexico! This beautifully appointed home includes 4 bedrooms (two of them being primary suites), a centrally located study perfect for midday meetings, an upstairs den set up as a 2nd entertainment area, and an upstairs loft perfect for reading or cards. This vacation home is
Stacey Cotter John R Wood Properties
$55,000 per month
270 5th Ave S Unit H-2, Naples, FL 34102
A rare opportunity located in the heart of Old Naples. This three-level residence offers simple and crisp spaces, creating a seamless flow from room to room with white limestone floors, imported Italian wood and glass custom doors and custom cabinetry in the kitchen and baths. A private interior elevator leads you to the additional floors featuring a fitness room, guest suites with custom
Nathan Dyer William Raveis Real Estate
$15,000 per month
155 1st Ave S, Naples, FL 34102
Welcome to your coastal retreat, just steps from the pristine white sands of Naples' famous beaches. Nestled on one of the most coveted and tranquil streets in Olde Naples, this timeless residence is now available as a long-term, unfurnished rental. Recently refreshed with new interior paint and updated landscaping, this home offers an ideal retreat for those seeking comfort, charm, and location.
Samantha Ford John R Wood Properties
$6,500 per month
473 12th Ave S Unit B8, Naples, FL 34102
Newly renovated in the heart of Olde Naples! Bonaire Club is part of the Village Green community providing amenities including large community pool, shuffleboard, bocce ball and club room. One block from Naples renowned Third Street South where you can find sophisticated and delightful shops, renowned restaurants and bistros and farmers markets every weekend. Two blocks from the beach and the
Michelle Combs Keller Williams Realty Naples
$12,000 per month
651 10th Ave S Unit 651, Naples, FL 34102
Charming Old Naples Retreat – Fully Furnished 2-Bedroom, 2-Bath Condo with Secluded Pool - Walk to Beach, Fifth Avenue and Third Street Restaurants and Shopping! Escape to paradise at this inviting, modern 2-bedroom, 2-bathroom condo, nestled in the heart of vibrant Old Naples at 651 10th Avenue South. Spanning 1,241 square feet, this turnkey gem is fully furnished and ready for your next monthly
Marybeth Alford Diversified Real Estate Group
$9,000 per month
1140 5th St S Unit A, Naples, FL 34102
Step into the epitome of coastal elegance at 1140 5th Street South, Unit A, located in the heart of Olde Naples, where charm, convenience, and luxury converge. This beautifully appointed vacation rental offers the quintessential Florida lifestyle just a short stroll from the world-renowned 5th Avenue South, Third Street South, fine dining, boutique shopping, and the sugar-white sands of Naples
Bill Archer Keller Williams Realty Naples
$16,000 per month
231 2nd Ave S Unit 102, Naples, FL 34102
$8.5K/month is for an Off-Season Lease only. Two blocks to Naples white sand beaches! This pristine and fully updated 2 BR + Den, 2 Bath condominium with 1,667 Living Area in in the delightful four-unit complex of Gulfwalk with southern exposure community pool. A seaside cottage in the heart of Olde Naples. Feels like a new, coastal home. Clean and bright, but warm and charming. This condo’s
Aaron Earls John R Wood Properties
$6,500 per month
766 Central Ave Unit 312, Naples, FL 34102
Available for the 2026 season. This 2 bedroom / 2 bath unit in Olde Naples is just 4 blocks north from 5th Ave South so you can walk or ride your bike to the downtown area where you can enjoy shopping, entertainment, dining and what Olde Naples has to offer. This small complex with mature trees and lush landscaping has a heated pool with a large area for poolside lounging, a sauna, BBQ area and
Charlie Wallen Naples Flat Fee Realty LLC
$19,995 per month
339 4th Ave N, Naples, FL 34102
Rare 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
$10,795 per month
1325 Gordon Dr, Naples, FL 34102
** GORDON DRIVE FULLY REMODELED COTTAGE FOR SEASON ** 2/2 ** BLOCK AND HALF FROM THE BEACH ** LUXURY ** Welcome to the oldest Cottage on Gordon Drive. This STUNNING completely remodeled 2/2 Cottage comes fully stocked with everything NEW! Located in Prestigious Olde Naples, FL. This luxurious 2 bedroom, 2 bath Cottage is just a block and a half away from the beautiful Naples white powdery-sands
Cheri Anne DeMonico Premier Property Management
$6,000 per month
1021 3rd St S Unit 102, Naples, FL 34102
Walk to the beach and Downtown Naples**ANNUAL or SEASONAL FURNISHED RENTAL AVAILABLE** 2 BEDS 2 BATHS ** Welcome to this beautiful coastal retreat! Fully furnished annual or seasonal rental! This newly renovated 2-bedroom, 2-bathroom first floor condo offers the perfect blend of comfort and convivence. Located within walking distance to the pristine Naples beach and the famous 5th avenue. Step
Angela Muscato Premier Property Management
$18,000 per month
320 Gulf Shore Blvd S, Naples, FL 34102
***DOWNTOWN***OLDE NAPLES***BEACH IS JUST A FEW STEPS FROM FRONT DOOR***4 BEDS/ 3 BATHS***FURNISHED SEASONAL***Stately charm and Olde Naples elegance await you in beautiful Villa Rosa, a classic Bahamian villa just steps from the sugar-sand beaches in Olde Naples. Four bedrooms and three full baths make this home the perfect spot for the whole family to enjoy! There's a large kitchen and living
Angela Muscato Premier Property Management
$10,000 per month
1222 Gordon Dr Unit 3, Naples, FL 34102
This condo is available for March and April 2026 only.2 Blocka ro Naples Pier Beach and 1 Block to all of the fun on 3rd avenue restaurants and shops! It doesn't get better than that. THis condo has been COMPLETELY redone and furnished with all new furniture from Baers! If you are looking for a perfect seasonal rental this is it. Parking place right behind the back door and a bike rack near
Marcie Roggow Douglas Elliman Florida, LLC
$49,500 per month
362 2nd Ave N, Naples, FL 34102
A welcoming Olde Naples retreat awaits at Neapolitan Sky! The stately Key West style home sits amidst lush landscaping on one of the prettiest tree-lined avenues in town, just a third of a mile from beach access. Approach the home from the circular driveway and enter across the the covered front porch. The main floor has an open white marble kitchen, dining area, living room, home office with
Stacey Cotter John R Wood Properties
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