Sterling Oaks in Naples is known as Florida’s premier tennis community but it is also so much more than that. With beautiful and peaceful lakes, stunning wildlife, and many local amenities, it is also a popular holiday resort best for staycations in Naples. Guests can also enjoy the clubhouse, fitness center, sauna, and bocce ball area. Did we mention, that it is also just a few minutes away from the ocean? You can sit out on the deck of your house, stroll along the quiet streets, or even have a barbecue party! On a Friday, head to the Tiki Bar after spending the day at either the Bonita or Barefoot beaches. To help you get the best out of your holiday, we’ve compiled a list of the best accommodations you can stay at. Read on to see our picks for the best Vrbo vacation rentals in Sterling Oaks, 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 October 19, 2025.
1. A cozy waterfront apartment
If you’re looking for cozy places to stay with your family, you’ll love this fully furnished apartment in Sterling Oaks, Naples, Florida. It offers a waterfront location with stunning views of the surrounding properties and a lush green lawn.
Soak in the simplistic, rush-free life of this community while relaxing in the screened dining area equipped with lounging chairs. Or you can indulge in socializing and exploring the Sterling Oaks grounds as you walk around the community pool or go for an invigorating dip in the shared hot tub. And while you’re at it, don’t forget to indulge in a game or two of tennis with other guests.
Forida, Florida, United States
2. Cozy property with modern kitchen facilities
With high vaulted ceilings, this holiday rental in Sterling Oaks, Naples, Florida, is contemporary and bright. Located on the second floor, it is an end-unit that boasts excellent views from the private patio area. It is comfortable and convenient–just a short distance to the beach and local amenities. This property has two bedrooms and can sleep up to six people. The master bedroom features a king-sized bed, the second room has two twin beds, and the third sleeping space is on the double futon in the common room. The kitchen is fully furnished and is the perfect place to cook up a delicious family meal.
Naples, Florida, United States
Top guest reviews
Host:
Owner is helpful and highly responsive to needsOwner is helpful and highly responsive to needsand there was a grocery store just down the road The owner was extremely helpful in answering any questions we hadThe owner was a pleasure to work withand I was so impressed with the location and the condo that I asked about the possibility of leasing for an additional week and then called the wife for a surprise vacationLocation:
The beach and the Mercato (plenty of fun shops restaurants bars and a movie theater) were 10 minutes awayPrior to heading to Naples on businessThe location is great within easy driving distance of recreation entertainment and retail activities We would recommend it without hesitationThe condo was within walking distance of the clubhouse and pool which was also very convenientThe community in which we stayed was very friendlyCleanliness:
The property was very clean and well-maintanedI highly recommend this condo to all generations Accurately described in ad Clean and smartly decorated great location for beaches/restaurants/I highly recommend this condo to all generations Accurately described in ad Clean and smartly decorated great location for beaches/restaurants/Read more reviewsAmenities & Room:
It also includes extras for the beach such as chairs towels and umbrellaThe condo also provided any and all amenities we needed during our entire stayThe kitchen is fully equipedThis condo has everything you need and more to have a great time in Napleswas From furniture to fixtures
3. Exquisite property with private parking, fire pit, and hot tub
As a recently remodeled property, this vacation rental is in immaculate condition. With space for up to eight guests, you’ll be happy to cook in the well-stocked kitchen which leads into the open-plan living room. The comfortable living room in itself is spacious and includes a relaxing L-shaped sofa. We adore the covered outdoor patio which includes a dining area, grill, and private hot tub. There is space for two cars to park securely on the property.
Top guest reviews
Host:
The owner was very assessable and overly accommodating I would not hesitate to stay at this beautiful house againCleanliness:
This house was exactly as described and picturedRead more reviewsAmenities & Room:
The house had everything that you can possibly need for a more than comfortable stay
4. Spacious and welcoming rental that feels like home
This partly open-plan designed property is located on the second floor and is an end unit. With its covered terrace, you can sit outside and enjoy the scenery whatever the weather. This property is beautifully decorated and will feel like a home away from home. The hosts have gone the extra mile to ensure that you have everything you need for your trip including beach chairs and coolers. There is dedicated parking for guests to use and full WiFi throughout.
Top guest reviews
Host:
owner helpful as can bethe owner was extremely nice to deal with and quick to offer any help desiredLocation:
it's location is ideal for all the activities & dining we pursuedwe particularly enjoyed the pool and walking through the various neighborhoodsCleanliness:
the condo was extremely clean & inviting when we arrivedthe condo is very well furnished and cleanRead more reviewsAmenities & Room:
the two televisions one in the living room and one in the den were a nice touch
5. Stunning three-bedroom home with garden area
With matching white-wash furniture and soft neutral colors this property is a relaxing haven. There are three bedrooms and three bathrooms making it ideal for a party of six guests. The kitchen is equipped with stainless steel appliances and has plenty of space for cooking. Guests can also relax in the comfortable living room which features a 55-inch (139.7-cm) Smart television and high ceilings. There are board games on site so everyone can enjoy a family game. We love the unique use of space in this property–even the loft area has been perfectly designed.
Top guest reviews
Host:
Amy for sharing your lovely home with usLocation:
The pool in the development is now my favorite pool in Naples and the beach is only minutes awayRead more reviewsCleanliness:
It was beautifully decorated and furnished with with everything we needed to enjoy our vacation
6. Wide property with two dining areas and modern amenities
With each of the four bedrooms having their own bathroom, guests will feel comfortable. The property is designed for ten guests and has some popular modern features. You’ll find inside a 50-inch (127-cm) smart television, a 500-movie DVD collection, and Bose Home Theater. The master bedroom also has a 52-inch (132.08-cm) LCD television and the remaining bedrooms each have 32-inch (81.28-cm) televisions. We think you’ll be much more likely to spend your time enjoying the private pool in the back garden. Also outside, you’ll find a patio, outdoor bar area, and dining space for ten people.
9752 Alhambra Lane
7. Tropical rental with pool and hot tub access and lakeside views
There are three bedrooms on this property–two with queen-sized beds while the master bedroom has a king-sized bed. In total, up to six guests can stay. This one-level property includes a pool area and hot tub for guests to take full advantage. The modern kitchen has recently been refurbished to include stylish stainless steel appliances. There is a small garden area which is ideal for older children to play in. We think that this vacation rental is a great family option.
Top guest reviews
Host:
my husband and I have rented The property is beautifully furnished with every amenity to allow a comfortable and home from home stay Before and during our month's ideal visit we were able to have c...Read more reviewsLocation:
Amazing beaches a vast choice of restaurants and shops are within a 10 minute driveSterling Oaks provides a lovely and safe environment as well as easy access to the surrounding areaFort Myers and Naples also give alternative locations for beaches leisure activities shopping malls and many entertainment venues including theatres and musical performancesHaving travelled from Scotland to this area for over 20 years this is the nicest villa
8. Contemporary and stylish home with new kitchen
This private property offers the best of the best for up to ten guests to enjoy. You’ll have a great time at the indoor pool which is surrounded by glass and has a dining table with beautiful views over the golf course. This property was renovated in 2018 and has a completely new, modern kitchen. This property has been decorated to be a tasteful single family villa. Many of the stylish decorations and furnishings are of Italian design. There are three bedrooms and up to five guests can stay comfortably.
Top guest reviews
Host:
The heated pool was spotlessLocation:
nice golf course view good shopping and restauarnts within a short driveWe really enjoyed Spanish Wells - it is a very friendly developmentCleanliness:
The home is clean with plenty of towels and decent linensRead more reviewsAmenities & Room:
The kitchen is well-equipped and the layout was perfectIt is one of the nicest properties that we've ever rented The owners obviously love their home
9. Luxurious home with a porch swing
Relaxation and Rejuvenation will be the defining words for your vacation at this home for rent in Sterling Oaks, Naples, Florida. This pristinely furnished vacation rental in Naples is bright and airy, complete with all the modern comforts. Bring your family here and spend quality time cooking meals together, drinking in the small in-house bar, or dining outdoors in the lanai area. You’ll also find a six-person hot tub in the lanai, perfect for washing away the stresses of city life with a warm soak.
Furthermore, the fenced backyard has fruit trees and a lush lawn. You can go for barefoot walks on soft grass or choose to soak in the tranquility from the porch swing in the lanai.
Naples, Florida, United States
10. Bright and trendy condo
You’ll love the vibrant and trendy styles of this beautifully furnished condo for rent in Sterling Oaks, Naples, Florida. With a chess-style tiled floor and snug furniture in its low-ceilinged space, the cozy place exudes a comforting vibe. Perfect for small families, this self-catering condo boasts a small kitchen with all cooking essentials. Furthermore, there are two dining spaces- the table next to the living room and one by the screened gate overlooking the surrounding grounds. You can either choose to enjoy quality time with your loved ones or sit with a book as you watch the sunset.
Furthermore, there’s a community Club House and an on-site restaurant where you can socialize with other guests and enjoy lavish dinners with your family.
Naples, Florida, United States
Spend a delightful holiday at Sterling Oaks
All of these beautiful Vrbo accommodations in Sterling Oaks, Naples, Florida are a perfect holiday destination. You’re spoilt for choice! Just make sure to have your camera ready as you enjoy all of the on-site amenities and the stunning local beaches that surround it.
Frequently asked questions about the best Vrbo vacation rentals in Sterling Oaks, Naples, Florida
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