$2,300 per month
1100 8th Ave S Unit 207C, Naples, FL 34102
Great location in the heart of Olde Naples.Short walk to Fifth AVE. Naples Beach Tin City and everything else Naples has to offer. This area is full of great restaurants and entertainment.This is a two bedroom two bath second floor overlooking the pool. This has a great pool a carport and extra storage.Available for annual rent starting July 1ST.
Brian Flannery Sun Realty
$54,995 per month
420 Palm Cir E, Naples, FL 34102
Beautifully 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
$16,000 per month
1490 5th Ave S Unit 200A, Naples, FL 34102
Live in ultimate waterfront luxury with fabulous resort amenities in the heart of downtown Naples! This condo is ideally located within the Naples Bay Resort Residences waterfront complex offering spectacular water views from walls of windows on both sides. An open floor plan features a gourmet eat-in kitchen with Wolf appliances and high top kitchen table that opens to the living room and
Stacey Cotter John R Wood Properties
$10,000 per month
401 Bayfront Place Unit 3306, Naples, FL 34102
Available Fall 2025! Luxury living & Location converge in this renovated 1,511 square foot, 2 bedroom, 2 bathroom home that has been updated, opened, and transformed into a coastal contemporary paradise. There is room to comfortably host and entertain in the eat-in kitchen, with access and connection to the balcony and living area. Need extra room for visitors, there are also two twin Murphy
Rob Mauceli Compass Florida LLC
$39,000 per month
655 Galleon Dr, Naples, FL 34102
Available: February - April. February & March: $39,000/month, April: $35,000/month. Nestled amongst grand oak trees and Royal Palms lies this Port Royal residence in a pristine setting on Galleon Drive. This home offers plenty of natural light throughout its open layout. Special highlights of the home include four bedrooms, four full baths, gracious gourmet kitchen, large and inviting living room
Lesley Garlock William Raveis Real Estate
$20,000 per month
739 7th Ave N, Naples, FL 34102
This gorgeously remodeled house is the ideal fusion of your modern coastal home and your Olde Naples beach cottage. Everything you need in a Naples vacation rental is present in this three-bedroom home with a den and three bathrooms. All rooms include hardwood and tile flooring, and the kitchen has been entirely rebuilt with new cabinets, countertops, stainless steel appliances, and a wine
Lesley Garlock William Raveis Real Estate
$6,500 per month
1309 Chesapeake Ave Unit 3-B, Naples, FL 34102
Property Information: Welcome to the epitome of waterfront living with yur own boat dock! Nestled within an exclusive enclave of only 8 meticulously crafted townhomes, this picturesque community offers a lifestyle of luxury and serenity and your very own private boat dock.. Perched majestically along the tranquil waterside at the opening to Naples Bay, the residence boasts floor to ceiling
Mary Ann Crooker Douglas Elliman Florida, LLC
$2,400 per month
440 Broad Ave S Unit 440, Naples, FL 34102
ANNUAL LEASE NOW AVAILABLE ON THIS TWO BEDROOM TWO BATH CONDO JUST A SHORT WALK FROM THE BEACH! PROPERTY COMES FULLY FURNISHED AND IS WELL PRICED. THIS IS A WONDERFUL OLDE NAPLES LOCATION CONVENIENT TO ALL THE ACTIVITIES INCLUDING SOCIAL EVENTS, DINING, SHOPPING, BEACH, 5TH AVE, THIRD ST, TIN CITY, BAYFRONT, ETC... AVOID THE CRAZY TRAFFIC AND ENJOY A SHORT WALK TO MANY OPPORTUNITIES. ANNUAL CONDO
Gerald Mathusek Downing Frye Realty Inc.
$5,500 per month
1549 Sandpiper St Unit 89, Naples, FL 34102
This charming, first floor 2 bedroom/2 bathroom condo is the perfect short or long term rental for simple, modern living. Completely renovated, this home boasts an open layout illuminated by natural light, new laminate wood floors and upgrades galore. This home features a spacious living area with brand new furniture, appliances and television, or effortless, turnkey living. Primary bedroom
Beth-Ann Cunningham Compass Florida LLC
$15,000 per month
1400 Nautilus Rd, Naples, FL 34102
Available now for rental.(Annual or Monthly or Seasonal.) Small pet on approval.Thirty day minimum in City of Naples. Fully furnished 4 bedroom, 3 bath with screened and heated pool. Walk to the beach at Lowdermilk Park. Annual 6000./month. Seasonal (November to April ) at 15,000.,/month. Off Season (6,000./month) Single family home. Fully furnished 4/3 with pool, family room, attached garage.
Monica Cameron John R Wood Properties
$7,500 per month
341 3rd Ave S Unit 341, Naples, FL 34102
Guests will enjoy this Lovely, cheerful and colorful property only 2 blocks to 5th Ave. S. in Old Naples. Walk to the beach (3 blocks) and walk to all the restaurants, shops and galleries for which Old Naples is famous! All this is possible and still enjoy reasonable rent. The living room offers a sofa and loveseat, TV, and sliding glass doors leading to a large patio with cushioned furniture
Maria Metzger Royal Shell Real Estate, Inc.
$20,000 per month
850 Central Ave Unit 305, Naples, FL 34102
This beautiful 3 bed, 2 bath unit is filled with modern touches and bright natural light. A boutique condo in a 22-unit building, you’ll find all the privacy and serenity you crave while living just steps from the beach and downtown life. The amenities are unparalleled - you’ll love the courtyard pool, outdoor green space and lounge hammocks, and rooftop summer kitchen and fire pit! Inside the
Ashley Baird Coldwell Banker Realty
$3,200 per month
450 Bayfront Place Unit 4201, Naples, FL 34102
Special Savings for Summer move-ins for this Light & Bright One Bedroom Bayfront condo. Discounted rent of just $2200/month for July through October 2025! Bayfront features resort-style amenities including 2 pools, 2 spas, a fitness center, grills, pickleball, tennis, and many outdoor spaces. Bayfront also is home to a selection of delicious restaurants, a unique waterfront Cabana bar, and an
Rob Mauceli Compass Florida LLC
$19,000 per month
1500 Pelican Ave, Naples, FL 34102
Annual Rental! Sunlight spills across the lanai, pool deck, and backyard, each space opening to the waterway—a clear path to the Gulf of Mexico through Naples Bay. This home, reimagined in a coastal contemporary style, greets you with an open heart: a seamless flow of kitchen, living, and dining areas, where light and connection define the space. It’s built for gatherings, yet offers room to
Nathan Dyer William Raveis Real Estate
$6,500 per month
950 7th Ave S Unit 23, Naples, FL 34102
Newly Remodeled 1-Bedroom Condo in Prime Olde Naples Location – Castleton Gardens. Discover the charm and convenience of Olde Naples living in this beautifully remodeled 1-bedroom, 1-bath condo located in the highly sought-after, gated community of Castleton Gardens. This turnkey residence offers a bright, open layout with brand-new furnishings, updated appliances, and the added convenience of
Elliot Barton Waterfront Realty Group Inc
$97,000 per month
440 Kings Town Dr, Naples, FL 34102
440 Kings Town Drive is one of the most exceptional luxury rentals in all of Naples. From the moment you enter the residence, to the master suite and the second master, you will be mesmerized by sweeping water views. Coastal elegance is replete in every detail, including an executive chef's kitchen, an ultra-luxurious master suite, a massive sunroom with adjacent formal dining and formal living
Michelle Craft Naples Homes and Rentals Inc
$47,250 per month
688 3rd St N, Naples, FL 34102
ANNUAL 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
$9,500 per month
1919 Gulf Shore Blvd N Unit 201, Naples, FL 34102
Welcome to The Diplomat Club- your ideal beachfront retreat on Naples’ prestigious Gulf Shore Boulevard North. This charming two-bedroom, two-bath condo offers the perfect blend of comfort and location for an unforgettable Florida getaway.Step inside to discover a bright, inviting living space bathed in natural light. A standout feature is the oversized screened balcony, offering breathtaking,
Kal Anderson Coldwell Banker Realty
$17,000 per month
2203 Gulf Shore Blvd N Unit E1, Naples, FL 34102
This Indies West condo in the Moorings lives like a home. Just steps to the white sandy beach and surrounded by water on 3 sides! Newly renovated 2 bed/2 bath condo with an open floor plan, floor to ceiling wall of sliding doors, wood floors, high end cabinets and appliances, tall ceilings, fireplace, and a one-car enclosed garage with extra storage. Kitchen has large refrigerator, microwave,
Bill Frantz Premier Sotheby's Int'l Realty
$20,000 per month
2201 Shad Ct, Naples, FL 34102
Escape to luxury in this stunning 4-bedroom, 6-bath waterfront property in prestigious Royal Harbor with 155 feet of water frontage and direct Gulf access, this fully furnished home offers exceptional indoor-outdoor living. The expansive lanai features a negative-edge pool, spa, outdoor kitchen, with illuminated landscaping and perfect for relaxing or entertaining. Inside, enjoy elegant finishes
Jessica Asbel Premiere Plus Realty Company
$15,000 per month
1400 Jewel Box Ave, Naples, FL 34102
Experience luxury coastal living at its finest in this stunning 4-bedroom, 4-bath waterfront property, in the heart of Naples’ Oyster Bay. Offering nearly 3,850 square feet of thoughtfully designed space, this fully furnished rental delivers the perfect blend of comfort, style, and direct water access. Enjoy seamless indoor-outdoor living with corner pocket sliders that open to a resort-style
Jessica Asbel Premiere Plus Realty Company
$15,000 per month
1471 Mandarin Rd, Naples, FL 34102
Nestled on a large, fenced and private lot with breathtaking sunset views, this sunny and cozy home offers the perfect blend of comfort and convenience. The fully stocked, brand new kitchen features sleek white quartz countertops and high-end stainless steel KitchenAid appliances - ideal for preparing everything from beach snacks to gourmet meals. Inside, luxury vinyl flooring runs throughout the
Adell Cotter Seaside Properties of South Florida, Inc.
$2,700 per month
1185 Cherrystone Ct Unit C, Naples, FL 34102
Prime Waterfront Location!Now available for annual rental, this charming 2-bedroom, 2-bathroom unit in Cherrystone Manor offers a unique blend of tranquility and convenience.Enjoy manatee watching, fishing, or simply relaxing from the private dock—with direct Gulf access for boating enthusiasts! Unit C features a north-facing view of the canal, bringing in beautiful natural light and serene
Jana DeNault Berkshire Hathaway FL Realty
$24,000 per month
888 10th St S Unit 101, Naples, FL 34102
Nestled between the iconic 5th Avenue South and the charming Third Street South, this exquisite 3 bedroom plus den, 4 bathroom villa is the ultimate winter retreat in Naples. Spanning nearly 4,500 square feet across four sun-drenched stories, the home features elegant furnishings, a neutral color palette, and refined finishes throughout. The inviting living room boasts a stylish sectional, rich
Sarah Wayne Gulf Coast International Lux R
$18,000 per month
1030 3rd Ave S Unit 105, Naples, FL 34102
Naples Square offers luxury living in the heart of downtown Naples! This 3 BR plus den/3.5 bath condominium lives like a single-family home with a private street entrance and attached private garage. The gourmet kitchen, with an induction cooktop, opens to the living and dining areas and has seating for 4 at the breakfast bar and the dining table seats 6. Boasting high ceilings, this two-story
Sarah Wayne Gulf Coast International Lux R
$14,000 per month
1030 3rd Ave S Unit 406, Naples, FL 34102
Available for Annual or Seasonal Lease! Your perfect rental! Discover your dream home in this stunning downtown Naples condo, which perfectly blends luxury and relaxed living. Spanning an impressive 1,529 sq. ft., the thoughtfully designed Ballard layout features two spacious bedrooms, two elegant bathrooms, and a versatile den—ideal for work or leisure. The heart of the home is the exquisite
Blaze Zdravev John R Wood Properties
$8,500 per month
980 7th Ave S Unit 201, Naples, FL 34102
Seasonal Condo downtown Naples. Walk to Beach.Spend the winter season downtown Naples. 5th Ave. is walking distance from this lovely end unit condo. Just steps to the pool on a quiet street that ends at the most beautiful beach with crystal blue water and white sand. Take a sunset cruise on the Naples Princess out to the Gulf of Mexico. Rent bikes or kayaks. Great walking area to stop for coffee,
Ann Bonilla Grice Realty Inc
$34,500 per month
1627 Murex Ln, Naples, FL 34102
Welcome to your new oasis in the heart of Naples! This exquisite 4-bed/3-bath rental property offers comfort, and convenience all in one package. Upon entering you'll be greeted by an open and airy floor plan filled with natural light. This home boasts an elegant design, featuring high-end finishes and modern fixtures throughout. The kitchen is a chef's dream, with top-of-the-line appliances and
Joseph Scott Compass Florida LLC
$25,000 per month
846 9th Ave S Unit 104, Naples, FL 34102
This impeccable villa is ideally situated in the heart of Olde Naples, just steps away from 5th Avenue South, Cambier Park, and Naples' pristine white sandy beach. Villas Ravello was designed to embrace abundant natural light throughout the entire home. The interior has been professionally curated with high-end décor and furnishings. In addition, the villa features a private courtyard complete
Samantha Ford John R Wood Properties
$7,000 per month
250 7th Ave S Unit 305, Naples, FL 34102
Great location! Two blocks to Naples pristine beaches! Within walking distance of all the Olde Naples and Historic Olde Naples has to offer! World famous restaurants, boutiques and specialty shoppes! This two bedroom, two bath condo has everything you need to enjoy the ambience of Naples, Florida. Very pleasant courtyard for your enjoyment!
J Bazzell Waterfront Realty Group Inc
$15,000 per month
392 7th Ave S Unit 4, Naples, FL 34102
Welcome to your coastal sanctuary at Olde Westlake Villas! This fully remodeled 2-bedroom, 2-bathroom plus den residence on the first floor offers the perfect blend ofluxury and convenience, just 4 blocks from the beach.Step inside and immerse yourself in the tranquility of this meticulously upgraded space. The master bedroom features a sumptuous king-size bed and a lavish ensuite bathroom
Joe Hoopfer Premier Sotheby's Int'l Realty
$39,000 per month
500 3rd Ave N, Naples, FL 34102
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 primary suite is located on the ground level and features a
Joe Hoopfer Premier Sotheby's Int'l Realty
$4,000 per month
1100 8th Ave S Unit 106C, Naples, FL 34102
Delightful corner unit 2 / 2 condo is totally upgraded and tastefully furnished. This well appointed home creates an up scale "Palm Beach Meets Naples VIBE" of casual and comfortable elegance. Condo provides an ultimate feeling of luxury from the spacious kitchen with high-end appliances to the dramatic bathrooms with floor to ceiling stunning tile and walk-in showers. All new Hurricane windows &
Carolyn Quistberg Premiere Plus Realty Company
$36,000 per month
374 14th Ave S, Naples, FL 34102
Key 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.
$6,700 per month
850 Central Ave Unit 202, Naples, FL 34102
Available Annually!!Experience the best of Naples living in this stunning 2-bedroom, 2-bath condo located in 850 Central—a sleek and modern boutique building with only 22 exclusive residences. Perfectly positioned just steps from 5th Avenue and a short stroll to the beach, this condo offers the ideal blend of privacy, style, and convenience. Inside, you’ll find a beautifully designed space with
Shannon Colon Reed Property Mgt. & Sales
$12,000 per month
231 3rd Ave S Unit 231, Naples, FL 34102
Welcome to 231 3rd Ave South...... AVAILABLE- Late Fall 2025 / Season 2026Indulge in luxury and convenience at this quintessential remastered Old Naples condominium.Perfectly situated in the heart of Olde Naples, you are just a short walk to the white sandy beaches and the abundant boutiques, galleries, cafes, and acclaimed restaurants, of 5th Avenue South. This exceptional location is ideal for
Sandra Malone John R Wood Properties
$12,000 per month
1910 Gulf Shore Blvd N Unit 204, Naples, FL 34102
SAND. SEA. SUN. This beautifully renovated 2-bedroom property is available for the full 2025-2026 season. Approximately 150 steps to the stunning Gulf of America beach. Amazing sunsets. Waves crashing. Crystal white sand. Azure blue waters. Not only do you have the beach, but in Coquina Sands you are close to all that Naples has to offer - fine dining, shopping and entertainment. Book 4 months
Patricia Moreno Naples Homes and Rentals Inc
$3,250 per month
1560 Blue Point Ave Unit 3, Naples, FL 34102
OWNERS WILL RENT LONG OR SHORT TERM. Welcome to a Boater's Paradise in Oyster Bay, where luxury meets convenience in this south-facing waterfront condominium. This rarely available unit in The Boathouse building offers stunning water views from every room. With 6 units and 2 stories, this high and dry building has weathered recent hurricanes, including IRMA, IAN, Helene, and Milton with
Kathy Knabel-Bailey Compass Florida LLC
$7,000 per month
410 Bayfront Place Unit 2204, Naples, FL 34102
Beautiful Bayfront 2 bedroom, 2 bath condo in the heart of downtown Naples. Live the sophisticated lifestyle in this mixed-use community that has everything. Just step downstairs to enjoy restaurants, art galleries, shopping, and marina. The community offers a secure building and parking garage, 2 pools, 2 Jacuzzis, a tennis court and 2 pickleball courts, an exercise room, a community room, and
Terese DeLuca Berkshire Hathaway FL Realty
$6,000 per month
1021 3rd St S Unit 200, Naples, FL 34102
AVAILABLE IN NAPLES 2025-2026 for your WINTER or fall vacation in OLD NAPLES!! Vacation close to the beach in this classic Town Manor 3 story condo with elevator on 3rd Street South featuring Two bedrooms with king and twins, two bathrooms, and updated kitchen. Corner unit with lots of light, glass enclosed 4 season lanai facing west towards the sunset and the beach, courtyard pool with lounge
Karen Wagenheim Downing Frye Realty Inc.
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