Delightful Naples Condo with large Resort Pool and Pickleball/Tennis Courts | Condo in Naples
2 Bedroom Condo in East Naples, Naples
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.
Delightful Naples Condo with large Resort Pool and Pickleball/Tennis Courts is located in East Naples. Delightful Naples Condo with large Resort Pool and Pickleball/Tennis Courts provides accommodation, featuring Air Conditioner, Security/Safety, Bedding/Linens, among other amenities. This Condo features Air Conditioner, Security and Bedding to make your stay a comfortable one.
Delightful Naples Condo with large Resort Pool and Pickleball/Tennis Courts has 2 Bedrooms , 2 Bathrooms, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Condo because of the excellent services rendered by the owner or manager of this Condo, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Condo has a friendly neighborhood, and the East Naples has interesting places to visit. If you want to learn more about the Condo in East Naples, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Policies
Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
FAQ's
Is this East Naples condo pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the East Naples condo have a swimming pool?
No, this East Naples condo does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in East Naples condo?
Best-rates for the East Naples condo starts from $73 per night with includes Laundry, Air Conditioner, Security/Safety, Bedding/Linens, Wellness Facilities, Fireplace/Heating, Child Friendly, Internet with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is East Naples condo a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this condo Good or guests have recommended them suitable for families. As reported by the owner or manager, the condo has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the East Naples condo wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the East Naples condo has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the East Naples condo?
Based on the information reported by the owner or manager, the East Naples condo indicates 1 day stay policy at this condo. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for East Naples condo?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
