Listed on 06/12/2026

Listed by Jessica Meschko

Days on market: 142

Property Status: Active Welcome to your downtown Naples beach retreat! This 2 bedroom, 2 bath residence has been completely re-imagined from the floor to the ceiling and is being offered as an annual rental! This light and bright end unit will wow you with its tasteful finishes and spacious rooms. The kitchen boasts a large island, Kitchen Aid and Bosch appliances, new shaker cabinetry, quartz countertops, luxury lighting fixtures, and breakfast nook. Both bathrooms have brand-new shaker cabinetry, fixtures, and finishes. All plumbing and electrical were replaced in 2023. This home has luxury vinyl throughout to withstand the elements of the beach lifestyle. This location offers its resident the best of Naples living. Located just steps from the world-famous Naples pier, sugar sand beaches, and within walking distance of Third Street South & fifth Avenue South, this location cannot be beaten! Walk to shopping, dining, and entertainment Office Phone: (239) 268-8976 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 09/09/2026

Listed by Chris Alley

Days on market: 53

Property Status: Active OFF-SEASON RENTAL - AVAILABLE THROUGH DECEMBER AND AFTER APRIL 2027. This listing is for OFF-SEASON stays, not January-March seasonal occupancy. 30-day minimum. Owner will consider discounted monthly terms for stays longer than 60 days. Experience Olde Naples, Naples Florida during one of the best times to enjoy it-fewer crowds, easier restaurant reservations, quieter beaches and the same walkable downtown lifestyle. This fully furnished 2-bedroom, 2.5-bath condo is ready for an extended Naples stay, temporary relocation, work-from-Florida escape or anyone who wants to enjoy downtown Naples without committing to the winter seasonal months. The split-level design gives everyone their own space. The main floor features a bright living and dining area, updated kitchen and convenient powder bath. Upstairs, both bedrooms have private en-suite bathrooms, making the layout ideal for visiting family, couples sharing the condo or anyone who simply wants more privacy. The condo is turnkey and move-in ready with updated flooring, refreshed cabinetry, contemporary lighting, impact-resistant windows and doors, hurricane shutters and in-unit laundry. Outside your door is the lifestyle people come to Naples for. Walk or bike toward the Gulf beaches and Naples Pier, head to Third Street South or Fifth Avenue South for dinner, browse boutiques and galleries, or spend an afternoon at Cambier Park. When you want to stay closer to home, relax at the community pool surrounded by tropical landscaping. This is the OFF-SEASON opportunity through December 2026 and after April 2027. Winter-season availability is offered separately. If you've been wanting to live in Olde Naples for a month-or stay awhile longer-without the crowds of peak season, this is an easy way to make Naples your home base. Office Phone: (239) 261-2244 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 10/26/2026

Listed by Chris Alley

Days on market: 5

Property Status: Active 2027 NAPLES SEASON - January, February and March currently available. 30-day minimum. Owner will consider discounted monthly terms for stays longer than 60 days. Spend winter where people dream of being-Olde Naples, Naples Florida, close enough to walk to the beach, Naples Pier, Third Street South and Fifth Avenue South. This fully furnished, turnkey 2-bedroom, 2.5-bath condo gives you the kind of Naples seasonal lifestyle that makes winter feel completely different. Start the morning with a walk toward the Gulf, spend the afternoon by the community pool or exploring downtown, then walk to dinner without having to plan your day around the car. The unique split-level floor plan gives the condo more privacy than you typically find in a seasonal rental. The main level offers a bright living and dining area, updated kitchen and convenient powder bath. Upstairs, each bedroom has its own private full bathroom, making it especially comfortable for couples traveling together, visiting family or extended seasonal stays. The residence is fully furnished and move-in ready with updated flooring, refreshed cabinetry, contemporary lighting, impact-resistant windows and doors, hurricane shutters, in-unit laundry and comfortable coastal furnishings. And then there's the location. The Gulf beaches, Naples Pier, Third Street South, Fifth Avenue South, Cambier Park, dining, boutiques, galleries and downtown Naples are all nearby. The community also offers a pool surrounded by landscaped grounds, giving you another easy place to relax when you're not at the beach. Beach mornings. Pool afternoons. Downtown dinners. Olde Naples evenings. If you've been waiting to secure your 2027 Naples Florida seasonal rental, this is the kind of location that lets you experience Naples the way you came here to enjoy it. Office Phone: (239) 261-2244 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.