Delightful Naples Condo with large Resort Pool and Pickleball/Tennis Courts

If you’re looking for an affordable, special place to get away and spend some time in Naples, Florida, our beautiful Winter Park condo may be just what you’re looking for. The Winter Park community offers a casual environment with mature landscaping throughout. The grounds are meticulously maintained. Buildings are limited to two stories and have ample open spacing between them. The community’s numerous amenities include one of South Florida’s largest pools, as well as eight dedicated pickleball courts, six tennis courts, and two bocce courts. Large palm trees line entrances, parking areas, and walking trails throughout Winter Park. Downtown Naples and its famously beautiful beaches are only minutes from the Winter Park community. There are miles of biking and walking trails easily accessible from the community. Winter Park offers a distinctly enhanced experience over high-rise condominium living.

Our beautiful two-bedroom, two-bath condo is located in a prime location within the community, only a few steps from the pool and courts. The second-floor condominium is furnished and decorated with a contemporary Floridian beach style. A screened entry lanai provides a comfortable place to enjoy an outdoor dinner, a cocktail, reading, and relaxing. The dining and entertainment areas are open-plan, with large windows providing a palm-framed view. There are two seating areas in the living room/entertainment space. An L-shaped sofa faces a large-screen TV, with a second lounge sofa providing a comfortable reading area. The dining table seats eight, with additional seating on the adjacent kitchen bar. The kitchen is fully equipped, complete with dishware, utensils, and serving ware. The primary bedroom has an adjustable king-sized bed, a full bath, and a walk-in closet. Furniture includes a full-size dresser, nightstands, and a large-screen TV. A second bedroom has a queen-size bed, a large dresser, a closet, and a TV. A full bathroom with a tub is adjacent to the bedroom. The condo also includes a full-sized washer and dryer.

There is a dedicated parking space for the unit as well as several other guest spaces available to tenants and visitors.

Currently available dates include the months of July through January 2027, with varying minimum stay requirements depending on the time of year. Monthly rental rates are also seasonally based. A 30-day minimum booking is required from June through November. December and January require a two-month reservation. Rental rates include all utilities. A refundable $1000 security deposit is required for all tenancies. No pets are allowed per HOA rules.

Monthly Rental Rates:

July, August $2000 mo. (1 month / 30-day minimum)

September, October $3000 mo. (1 month / 30-day minimum)

November $3600 mo. (1 month / 30-day minimum)

December/January $4200 mo. (2 month / 60-day minimum)

Discover the perfect Naples getaway at our inviting and affordable Winter Park condo. Nestled in a beautifully maintained community with lush, mature landscaping, Winter Park offers a relaxed, welcoming atmosphere, spacious low-rise buildings, and open spaces. Enjoy one of South Florida’s largest resort-style pools, eight dedicated pickleball courts, six tennis courts, and two bocce courts—ideal for active guests. Stroll beneath towering palm trees lining the entrances, parking areas, and scenic walking trails that wind through the neighborhood. Just minutes away, you’ll find vibrant downtown Naples and its renowned beaches, while miles of biking and walking trails are easily accessible from the community. Experience the comfort and charm of Winter Park—an exceptional alternative to high-rise condominium living.

Experience comfort and style in our spacious two-bedroom, two-bath condo, ideally situated just steps from the pool and courts within Winter Park. Located on the second floor, this condo features contemporary Floridian beach-inspired decor and furnishings. Begin your day or unwind in the evening on the screened entry lanai—perfect for outdoor dining, cocktails, reading, or simply relaxing. The dining and entertainment areas are open-plan, with large windows providing a palm-framed view. In the living room, an L-shaped sofa faces a large-screen TV, while a second cozy lounge offers an inviting reading nook. The dining table comfortably seats eight, with additional bar seating adjacent to the fully equipped kitchen, which includes all dishware, utensils, and serving ware. The primary bedroom boasts an adjustable king-sized bed, a full bath, a walk-in closet, a dresser, nightstands, and a large-screen TV. The second bedroom provides a queen-size bed, ample storage with a dresser and closet, and its own TV. An adjacent full bathroom with a tub, plus a full-sized washer and dryer in a utility room, complete the home’s thoughtful amenities. There is a dedicated parking space for the unit as well as several other guest spaces available to tenants and visitors.

Availability runs from June through January 2027, with minimum stay requirements and seasonal rates. Bookings from June through November require a minimum stay of 30 days, while December and January require a two-month reservation. All monthly rental rates include utilities. A refundable $1,000 security deposit applies to each tenancy. Please note that pets are not permitted due to HOA regulations.

Important Rental Information (Winterpark HOA Approval Required)

Please note that all Winterpark rentals require HOA approval before occupancy. This is a community-wide policy managed by Cambridge Property Management in Naples, FL.

After booking, all guests must:
• Complete the HOA Lease Application
• Sign the Pre-Rental Compliance Agreement
• Provide a $150 non-refundable HOA application fee (payable to Cambridge Property Management)
• Complete a background check through ApplyCheck (required for every tenant, including international guests)

The HOA typically issues approvals within 2–3 weeks of receiving completed materials.

If, for any reason, your application is not approved, your booking will be fully refundable.