Winter Park is a wonderful gated community close to downtown Naples, Florida. It is close to all the important places of the town and it is loaded with amenities that will make your stay a comfortable one. It has a clubhouse, tennis courts, pickleball court, bocce ball court, a walk/jog trail, stores/restaurants, a library, and a resort-style community swimming pool. So many condos for rent in Winter Park are available as private accommodations for guests vacationing in Naples. These condos are spacious, fully equipped, and are located at an easy distance from the beaches of the town. To plan the perfect holiday, read below to find the best Vrbo vacation rentals near Winter Park in Naples, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Lavish Scandinavian-style home with pool and hot tub (from USD 571)
Located within 10 minutes of downtown and the stunning Gulf beaches, this vacation home is a dream holiday home. With the heated pool and hot tub available, you can relax and unwind. You can chill on the beach chairs and enjoy your favorite drink by the poolside. You can spend a fun-filled afternoon barbecuing hot dogs or steaks on the grill and enjoying poolside dining.
Additionally, you can play badminton or enjoy swinging in the lush green setting. You are welcome to wander around the tropical English-style garden to pick fresh avocados, oranges, and lemons. In the evening, you can sit around the fire pit and roast s'mores.
2. Luxurious waterfront house with boat dock and pool (from USD 579)
Located near downtown, this beach house rental in Naples is the ideal holiday spot. For your relaxation and enjoyment, a private heated pool and beach chairs are available. The accommodation also provides bicycles to explore the nearby area.
You can bring your furry friends to the property. The home is also kid-friendly with baby gates and dishes for children available. You can prepare your favorite recipes in the fully equipped kitchen. For entertainment and leisure purposes, there is a television and free Wi-Fi.
3. Spacious two-bedroom villa (from USD 140)
Surrounded by lush, green trees and lawn spaces, this luxury villa in Naples has two bedrooms and a bath, and it is perfect for a family vacation. The house has a private deck overlooking Glades Golf & Country Club golf courses. The house is located conveniently close to two golf courses, tennis courts and the clubhouse within the community. The villa has a spacious floor plan with granite table tops. It has been recently renovated. Guests get free access to the community pool and golf courses during their stay.
Top guest reviews
Amenities & Room:
The place is completely renovated with comfortable furnitureHost:
Then you have dozens of restaurants to choose from with in a one mile radiusRead more reviewsLocation:
We took our bikes and found we could bike just about anywhere we wanted to go in Naples With a short bike ride we were down at the beach or downtown at the art fairThe Pines course was reseeded last year and is in excellent conditionThe location is so unique because you can play golf and be sitting in your living room 10 minutes later having a glass of wine
4. Lake-view home with elegant interiors (from USD 250)
This modern and stylishly decorated rental near Winter Park, Naples, comes with a beautiful view of Crown Pointe Lake as well as the massive golf courses in the community. The house is close to the community fitness center and tennis courts. There is a covered lanai with a vast lounge area for you to sit by the pool and relax. There is also a grill facility in the lounge area so that you can enjoy delicious outdoor meals by the poolside. The house is spacious and can accommodate a big crew as well as pets.
Top guest reviews
Amenities & Room:
The property had everything one would need and moreThe response time is beyond excellentThe house was perfect and has everything you could possibly need during our vacationwell kept up kids had a real good time would like to rent again next yearAll the information one needed was listed in the manualHost:
Tammy and Neil were very attentive and answered any questions we hadShe is literally a text message awaythe dishwasher and washer and dryer are very noisy and the garage door was not functioningvery well appointed and confortable location nice and clean andand we are looking forward to returning for our next family tripRead more reviewsLocation:
Space was never an issue eitherWe loved the house and the entire renting process was simple and easyThe house was very clean (except for the bbq) and fully equiped A few downsides: in the winter there is hardly any sunshine in the poolareaThe property is exactly as advertised Close and convenient to restaurants mallsThe neighborhood is very quiet and well situated
5. Vacation home with private pool and landscaped garden (from USD 295)
Beautifully landscaped lawns and a private pool with a lanai on the outdoors, and hardwood and granite furnished home on the inside, this is the perfect space for a perfect vacation. The house is decorated with attractive and subtle pastel colors that go well with the wooden furnishings. You can enjoy the breathtaking views of the palm grooves while relaxing inside the heated pool or sipping your favorite drink in the screened lanai. There is ample seating on the outdoors as well.
Top guest reviews
Amenities & Room:
I'm not a fan of climbing stairsThere is a "mother-in-law suit" or to be more specific a marvelous part of the house with a separate kitchen bathroom 2 bedrooms and all the privacyNo leased home is problem-freetheir top priority was our comfort and enjoymentan added bonus of the poolCleanliness:
It was clean close to the beachesHost:
Very responsive I texted her to get some advise about the areaThey are as amazing as their propertyThe grandparents and our family had some privacy while still connected Beautiful poolwere available for any questions or issues and were very personableI had the chance to meet the ownerRead more reviewsLocation:
It is not my first time renting a house for vacationmy kids just loved it Nice and safe neighborhood 10mn to a nice beach and downtown 5mn to grocery stores 5mn from many doctors offices and urgent careA lot of thought went into the home's design HereThe downstairs is practically a separate independent house on its ownThe heated pool was used every day or twice per day by my fife son and daughter-in-law
6. Elegant pool home (from USD 376)
The Rovigo vacation rental in the Kings Lake community is a stylish-looking home with attractive blue hues and wooden furnishings. The house is quite spacious for a small family vacation. There is a pool inside the screened lanai of the house, where you can enjoy your favorite barbecue grill dishes as well as a swim. The house is located at a convenient distance from the Naples beaches and other downtown areas.
Top guest reviews
Amenities & Room:
the kitchen had everything we neededHost:
Maria was great to work withShe even sent over options to play golfWe had a very good time cperienceThe pool was great property was cleanEXCELENTE LA PROPIEDAD ESTÁ EN CONDICIONES OPTIMASRead more reviewsLocation:
Particularly liked the 2 golf courses at Lele just a short walk from condoPATRICIA Y ROMINA DE LA OFICINA FUERON MUY
7. Spacious lake-view villa with a pool
Enjoy the blissful views of Crown Pointe Lake from your home. This luxurious villa has four bedrooms and a spacious living room that can accommodate up to 10 guests. The house has a pool on the front side, from where you can relax and enjoy the view of Crown Pointe Lake. Surrounded by a beautiful garden with tall palm trees, this house has a lanai for chilling out as well as a garage. Enjoy the delicious meals cooked in the fully stocked kitchen in both the indoor and outdoor dining areas. Make memories for life with your big family in this great vacation rental.
4.51 km (2.9 mi) from Naples Botanical GardenAccommodates: 8
Minimum Nights: 6
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Amenities & Room:
The children enjoyed the large pool overlooking the lakeThe house was immaculate with comfortable beds a well equipped kitchen and charming decor that made it feel like a home away from homebut it was public parkingIt needed to have been rinsed down better and the cushions were a little mustyThe kitchen was fully supplied with dishes and utensilsCleanliness:
The house was spacious lovely and cleanThere were plenty of linens and bath towels(I am very particular and I was extremely pleased) andThe house was very clean and organized The neighborhood was lovely and quiteLawn was maintained and well kept Bathrooms and bedrooms were all very clean Fresh blankets and sheets for each bed with additional sheets if neededHost:
He was also very quick to respond to our questionsWhen we arrived we found the home cleanScreened in pool was a MUSTbut these were taken care of and communication was easy both before and during our staybut I suppose it would have been nice to know this before hand All in all a great holiday in a beautiful house that was tastefully decorated and cleanRead more reviewsLocation:
Tech brought his significant other on call Loud cars traveling in neighborhood late at night House not walk to beaches or downtown SliderPublix Grocery store was exactly 1 mile from the house which made it super convenient to get groceries as needed Plenty of shopping within 5 miles Starbucks right down the road with drive through...the local grocery was only a few minutes away sowell situated About 10 minutes to the beachWe found this home to be top notch and just what we wanted at only 10 minutes to the beach and 5th
8. Lake-view pool home close to the beach
Last on this list is a lovely lake-view home with a spacious lounging area. The house has a big porch with ample seating and dining arrangements along with an outdoor grill. This rental has three bedrooms and a separate stocked kitchen that’s fully equipped with the necessary equipment and utensils. There is a bathtub for you to relax during your vacation. Guests are provided with all the necessary beach gear. You can also enjoy a game of golf or tennis in the community.
4.27 km (2.7 mi) from Naples Botanical GardenAccommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Amenities & Room:
The kitchen is well equipped so cooking was easyKitchen was very adequate and has an outside grillWe spent each day outside by the pool including mealsCleanliness:
The house is very clean and great layoutThe house is beautifully decoratedThe house is beautiful and very cleanThe beds were very comfortable and everything feels clean and functional Thanks for a great weekHost:
A perfect rental experience Good communication with care takers and ownersThe home was pristine and well furnished additional lovely view Close to 5th and 3rd along with beachesa nice pool and is well stocked with kitchen utensils and suppliesThe outdoor area including the pool were terrificRead more reviewsLocation:
The location is so good to downtown and many other great spots
Cozy homes for a memorable beach vacation
While enjoying the pristine waters and the white sands of the Naples beaches is great, when combined with expansive golf courses, tennis courts, community facilities and spacious pool homes, it makes it the perfect way to spend a vacation. Make memories that will be cherished forever by your family, friends, kids and pets in these amazing Vrbo private accommodations that are available at discounted prices. Hurry up! Grab the best of Vrbo deals for your next Winter Park, Florida trip.
Frequently asked questions about Vrbo vacation rentals near Winter Park, Naples
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