Available for the 2027 season (90-day minimum per HOA). If your idea of the perfect winter in Naples Florida includes morning beach walks, sunset skies, and an easy “we don’t need a car for everything” lifestyle—this Gulf Shore Boulevard condo is exactly that. This 2-bedroom, 2-bath coastal retreat is a short walk to the sand, so beach time can be spontaneous—no planning required. Start the day

Chris Alley

Downing Frye Realty Inc.

(239) 522-2897

ANNUAL RENTAL RATE! Charming rental in the heart of Olde Naples, just minutes from 5th Ave South, 3rd St South, beaches, dining, and shopping. Bright living spaces with a comfortable layout. Located on a quiet street yet close to all downtown Naples has to offer. Ideal for enjoying the Naples lifestyle. UTILITIES INCLUDED!

Enjoy the Naples lifestyle from this beautifully furnished seasonal condo in the heart of Olde Naples. Featuring a bright open layout, elegant décor, and inviting living spaces, this residence offers both comfort and style. Just a short stroll to 5th Avenue South, charming cafés, boutique shops, and the beach—perfect for your winter retreat in paradise.

Seasonally $14,000/month and annually offered at $7,000/month. Live Life Beautifully in Southwest Florida in the Mews of Naples. Experience the ultimate Naples lifestyle in The Muse of Naples, a turnkeyfurnished single-family home located in the prestigious Park Shore community. Just west of US-41 and only blocks from the beach, thisbeautifully appointed 3-bedroom + den, 3-bath residence

Keri Huber

John R Wood Properties

(239) 366-4615

Available off season for $3,500/month, Jan and April 2026 @ $5,000/month. "Live Life Beautifully In Southwest Florida" in the Jewel on 4th. This stunning remodeled 2nd floor condo is centered in the heart of Olde Naples. Just 1 block to 5th Ave shops, dining, art & culture. The Jewel on 4th sleeps 4 comfortably with a Queen size pull-out sofa in living room. Home was renovated from top to bottom

Keri Huber

John R Wood Properties

(239) 946-1744

Annual Rental available at this fabulous condo! Nestled between the Bay and Gulf, this beautiful, newly renovated condo is the epitome of coastal luxury in the heart of Naples! This corner, turnkey unit is located on the 4th floor where you will be able to enjoy life in Park Shore. The prime location adds to the charm of Venetian Cove Club and offering a stroll to some of the best shops and fine

Jane Wood

John R Wood Properties

(239) 522-7388

Gorgeous Naples Bay Front Condo available for short- or long-term lease!Located on the beautiful Gordon River in Naples, FL, this stunning condo offers exceptional waterfront living with direct access to the best of Naples. Enjoy serene views, premium coastal living, and close proximity to top dining, shopping, and beaches. Perfect for seasonal stays or year-round enjoyment. Let the

TOES IN THE SAND! A ONE-OF-A-KIND BEACHFRONT CONDO IN THE HIGHLY DESIRABLE COQUINA SANDS NEIGHBORHOOD OF NAPLES FL AT THE SURFSIDE CLUB! Totally remodeled 3 bedroom, 2.5 bath 2nd floor unit with a fully equipped white kitchen with stainless steel appliances, in-residence laundry room with full size washer and dryer, luxury vinyl flooring, built-in cabinetry, large screen TV and a spectacular

Laurie Bellico

William Raveis Real Estate

(239) 276-6281

687 9th Ave S is a short distance to fabulous dining on 5th Avenue, shopping on 3rd Street South, tennis and other fun at Cambier Park, relaxing at the Naples Beach, and boating on Naples Bay. Live in the heart of Olde Naples in this two-story home with a first-floor master suite. This turnkey furnished abode offers cozy bedrooms and light & bright living spaces as well as high end appliances

Jane Wood

John R Wood Properties

(239) 893-7610

This gorgeous Olde Naples rental offers a luxurious, private courtyard setting in a highly sought after location, near the sugary beaches and Naples bay. The unique design features 4 bedroom suites with private baths, a private cabana, and a 2-car garage. The first floor hosts a fantastic open concept great room and kitchen, one of the bedroom suites, plus a covered lanai with an outdoor kitchen

Jane Wood

John R Wood Properties

(239) 364-7522

Enjoy the heart of Olde Naples in fantastic 888 10th Ave S! The home features four bedrooms in the main house and a separate private guest cabana above the garage. This spacious floor plan can easily accommodate a large family as well as your guests. Many of the stunning features of this home include 11 foot ceilings, Legno Bastone Flooring, UMI quartz countertops, Thermador Professional Series

Jane Wood

John R Wood Properties

(239) 667-4914

Location, location, location! The all new FOUR SEASONS with restaurants plus a marketplace has opened and is a great addition to this gulf shore neighborhood. The Del Mar is a dignified building on the corner of Banyan Blvd & Gulf Shore Blvd in Coquina Sands across from Lowdermilk Park, one of the best beaches and waterfront areas in Naples! This 4th-floor unit with SW exposure features

Laurie Bellico

William Raveis Real Estate

(239) 946-2568

AVAILABLE NOVEMBER 2026 THROUGH APRIL 2027!!! This pristine 2 bedroom, 2 bath condoat Naples Continental Club in the Moorings is a beautiful seasonal rental in a resort style community . Situated on the 6th floor with gorgeous views of the Gulf of Mexico, this ideal seasonal rental is centrally located in Naples with a short drive to 5 th Ave, Venetian Villiage and Waterside Shops.

Jack Breyman

DomainRealty.com LLC

(239) 427-8978

"Live Life Beautifully in Southwest Florida" in the Mews of Naples. Experience the ultimate Naples lifestyle in The Muse of Naples, a turnkey furnished single-family home located in the prestigious Park Shore community. Just west of US-41 and only blocks from the beach, this beautifully appointed 3-bedroom + den, 3-bath residence offers a seamless blend of elegance, comfort, and coastal

Keri Huber

John R Wood Properties

(239) 423-8497

One will have no choice but to fall in love with Sunny Naples, FL after residing in this recently updated and decorated open floor plan unit situated within the heart of Downtown Naples. Take your pick of daily views from the private balcony overlooking iconic 5th Avenue South or enjoy breathtaking sunrises and sunsets from the rooftop pool overlooking Cambier Park! 780 5th Avenue South is an

Blair White

John R Wood Properties

(239) 758-9946

Location, location, location! Live the good life in the highly desirable Coquina Sands neighborhood, just minutes from downtown Naples and around the corner from the brand-new Four Seasons Resort with restaurants and marketplace. This dignified building is perfectly positioned at the corner of Banyan Blvd and Gulf Shore Blvd N, directly across from Naples’ sugar-sand beaches and iconic Lowdermilk

Laurie Bellico

William Raveis Real Estate

(239) 719-5781

"Live Life Beautifully in Southwest Florida" in this stunning, remodeled waterfront condo in Marina Manor, located in the heart of downtown Naples. This spacious residence features stylish shiplap accents & tile flooring throughout, a modern and sophisticated kitchen with stainless steel appliances, and breathtaking views of the Gordon River—where you can watch boats pass by and enjoy the best of

Keri Huber

John R Wood Properties

(239) 360-6465

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

"Live Life Beautifully in Southwest Florida" Nestled in the highly desirable Naples Heights neighborhood between Goodlette-Frank Road and US-41, this charming four-bedroom, two-bath cottage offers the perfect blend of comfort, convenience, and coastal living. With coveted western exposure, the home is ideal for enjoying stunning sunsets, whether as a winter retreat or a full-time residence. The

Keri Huber

John R Wood Properties

(239) 456-1090

"Live Life Beautifully in Southwest Florida" Nestled in the highly desirable Naples Heights neighborhood between Goodlette-Frank Road and US-41, this charming four-bedroom, two-bath cottage offers the perfect blend of comfort, convenience, and coastal living. With coveted western exposure, the home is ideal for enjoying stunning sunsets, whether as a winter retreat or a full-time residence. The

Keri Huber

John R Wood Properties

(239) 544-5047

"Live Life Beautifully in Southwest Florida" in this lovely top floor condo (with common elevator) in the highly sought after community of Hidden Lake Villas. This 2 bedroom 2 bathroom home is just perfect for a long seasonal getaway in Naples, FL. Just blocks from Venetian Village, Local Beaches, 10 minutes to Mercato & Downtown you can have it all within minutes from this condo. Looking for a

Keri Huber

John R Wood Properties

(239) 510-2052

Experience the pinnacle of downtown living in this completely renovated residence. Every inch of this home is brand new, offering a fresh, modern aesthetic in one of the most sought-after zip codes in Florida. Whether you are looking for a year-round home or a sun-drenched seasonal escape, this property delivers "All-New Everything" in an unbeatable location. KEY PROPERTY HIGHLIGHTS:PRIME

Maxim Vulpe

Parkline Realty

(239) 499-4867

Chic 2-Bedroom, 2-bath condo in the Heart of Olde Naples! Welcome to your dream retreat in downtown Olde Naples! This beautifully updated 2-bedroom, 2-bathroom condo at 365 5th Avenue South #303 offers an elegant blend of style, comfort, and convenience just steps from the best of Naples. Located on Naples’ famous 5th Avenue South, with world-class dining, boutique shopping, and art galleries

David Puskaric

Parkline Realty

(239) 236-3905

Annual rental available! Furnished second-floor unit located in highly desirable Olde Naples. Enjoy a walkable lifestyle just minutes from 5th Avenue South, beaches, dining, shopping, and Cambier Park. Interior features include a dishwasher, microwave, and in-unit washer and dryer. All utilities included.

Annual rental available! Furnished second-floor unit located in highly desirable Olde Naples. Enjoy a walkable lifestyle just minutes from 5th Avenue South, beaches, dining, shopping, and Cambier Park. Interior features include a stove, refrigerator, dishwasher, microwave, and in-unit washer and dryer. All utilities included.