Oakes Estates vacation rentals

We found 63 vacation rentals — enter your dates for availability

Discover a selection of 12 homes and other vacation rentals in Oakes Estates that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.
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Find out more about Oakes Estates

Find out more about Oakes Estates

Why visit Oakes Estates

  1. Tranquil neighbourhood: Oakes Estates provides a peaceful atmosphere perfect for family vacations and relaxation.
  2. Outdoor activities: The area is ideal for outdoor enthusiasts, offering ample opportunities for adventure and exploration.
  3. Charming nearby attractions: Discover the attractive city of Naples, renowned for its stunning beaches and vibrant community.
  4. Diverse accommodation options: Enjoy a variety of vacation rentals, from private homes to spacious villas, catering to all preferences.
  5. Friendly locals: Experience the warm hospitality of the community, making your stay even more memorable.

Popular types of accommodation around Oakes Estates

Vrbo offers a variety of vacation rentals in Oakes Estates, perfect for your getaway. Whether you prefer a private vacation home, a cozy condo, or a spacious villa, there's something for everyone. Many of our properties feature ample parking and generous room sizes, ensuring you have all the space you need to relax. Explore the charm of Sterling Oaks and find the ideal accommodation for your stay in this beautiful area.

  • Houses: The top choice for visitors, these spacious homes offer privacy and comfort, perfect for families or groups enjoying Oakes Estates.
  • Condos: A popular option for those seeking modern amenities and a community atmosphere while exploring the area.
  • Villas: Elegant and often luxurious, villas provide a stylish retreat with added privacy and beautiful surroundings.
  • Apartments: Ideal for solo travellers or couples, these rentals offer convenience and a home-like feel.
  • Cottages: Quaint and charming, cottages offer a cozy escape with a touch of rustic charm.**

Top attractions around Oakes Estates

Oakes Estates in Naples, Florida, offers a delightful getaway for families and outdoor enthusiasts alike. With its beautiful beaches, urban parks, and vibrant streets, visitors can enjoy a mix of relaxation and adventure. The area is perfect for those seeking cultural experiences and outdoor activities, making it an ideal destination for a memorable vacation. Whether you're looking to unwind by the beach or explore local attractions, Oakes Estates has something for everyone.

  1. Vanderbilt Beach: A stunning destination with soft white sands and beautiful sunsets, perfect for sunbathing, swimming, and beach walks. The laid-back atmosphere invites relaxation and enjoyment of the coastal scenery.
  2. Fifth Avenue South: This bustling street features chic boutiques, art galleries, and diverse dining options, offering a vibrant urban experience. The lively atmosphere makes it ideal for leisurely strolls and enjoying local culture.
  3. North Collier Regional Park: A family-friendly urban park with lush greenery, playgrounds, and walking trails. It's a great spot for picnics, outdoor activities, and connecting with nature while being close to the city.

Things to do recommended for couples

For a romantic getaway in Oakes Estates, indulge in the luxury of Bonita Bay East, a private country club just 8.0km away. For a fun twist, try Golf Safari Mini Golf, located 11.3km away, perfect for a playful day together amidst adventure and sports vibes.

Things to do recommended for families

Your family will have a blast at Sun N Fun Lagoon, a vibrant waterpark just 1.6km from Oakes Estates. For sports enthusiasts, the Paradise Coast Sports Complex, located 12.9km away, offers exciting facilities and activities that everyone can enjoy together.

Things to do recommended for groups

Groups visiting Oakes Estates can enjoy a round of golf at Tiburon Golf Club, shop and dine at Mercato, or try their luck at the Naples-Fort Myers Greyhound Track for a fun-filled evening. Each venue offers a unique local vibe perfect for group adventures.

What do I need to keep in mind when booking a vacation around Oakes Estates

When planning your trip, whether you're traveling with a group, with family, bringing your pets, or seeking extended stays, be sure to prioritize your preferences in your search. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oakes Estates with a group: Think about the number of bedrooms you'll require, along with amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Oakes Estates with young kids: Traveling with young children can present its challenges. It's essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Oakes Estates: For many families, a trip isn't truly fulfilling without their furry companions. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakes Estates: If you're in search of vacation rentals offering discounts for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Oakes Estates

Oakes Estates in Naples, Florida, is a tranquil neighborhood perfect for family vacations and outdoor adventures. Surrounded by stunning large estate homes, you’ll enjoy a family-friendly atmosphere that invites relaxation. Nearby, explore the charming city of Naples, known for its beautiful beaches and vibrant community. With friendly locals and romantic spots, Oakes Estates is an ideal base for discovering the best of Southwest Florida while enjoying the comfort of a serene retreat.

  • Bonita Springs: Located 9.7km from Oakes Estates, Bonita Springs is a vibrant city renowned for its stunning beaches and outdoor recreational opportunities. Families flock here to enjoy quality time at the local beaches, while golf enthusiasts can take advantage of the numerous golf courses available. The city also features a recreation centre, ensuring there’s always something for everyone. Notable attractions include the pristine family-friendly beaches and nearby islands, making it a perfect spot for relaxation and adventure.
  • North Naples: Just 6.4km from Oakes Estates, North Naples is a charming village that attracts visitors looking for a blend of beach fun and outdoor activities. This area is ideal for families, with inviting beaches and well-maintained golf courses. The local recreation centre is a hub for community activities and sports. With easy access to beautiful family beaches and nearby islands, North Naples offers a delightful escape for those wanting to enjoy the sun and surf.
  • Tarpon Bay: A mere 1.1km from Oakes Estates, Tarpon Bay is a picturesque neighbourhood that caters to outdoor enthusiasts and sports lovers. With a focus on beach activities, this area boasts excellent golf courses and a luxurious resort experience. Visitors can relax and unwind at the nearby family beaches and explore the scenic beauty of the islands. Tarpon Bay is perfect for those seeking an active vacation filled with sun, sports, and stunning coastal views.

Best time to go to Oakes Estates

If you're planning a trip to Oakes Estates, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January65.7°F (18.7°C)No Rain (Dry)Mostly SunnyHighAverage
February68.2°F (20.1°C)No Rain (Dry)SunnyHighSlightly High
March70.3°F (21.3°C)No Rain (Dry)SunnyHighSlightly High
April75.4°F (24.1°C)No Rain (Dry)SunnyAverageAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnyAverageAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnyLowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyLowSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnyLowSlightly Low
November73.0°F (22.8°C)No Rain (Dry)Mostly SunnyAverageAverage
December69.3°F (20.7°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, refine your existing travel arrangements, or manage your bookings. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Oakes Estates?
The most desirable types of vacation rentals in Oakes Estates are houses. Hoping for something different? Vrbo has numerous options to match our guests’ needs, so you’ll see vacation properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Oakes Estates?
The average price for a vacation rental in Oakes Estates is based on a number of factors, such as season, length of stay and property type. Whether you’re dreaming about a sprawling villa with lots of bedrooms or a quaint cabin that’s perfect for two, just enter your travel dates to discover stays with amazing value.
How much does it cost to rent a beach house in Oakes Estates?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside vacation rental. Click on your Oakes Estates travel dates to see all your options on Vrbo. Can’t live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want in your beach house.
Are there pet-friendly vacation rentals in Oakes Estates?
Good news. There are. You can pick from 14 vacation homes that welcome pets in Oakes Estates on Vrbo. Our cuddly best friends need a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where Rover can join the fun.
Can I rent a house with a pool in Oakes Estates?
Pack your swimming gear and inflatable lounger, because there are nine houses with a private pool in Oakes Estates. Book a stay at one of these terrific vacation rentals and make every day a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find a place to make a splash!
What are popular rental amenities in Oakes Estates?
A water view, a fireplace and a firepit top the list of most popular rental amenities in Oakes Estates. Whether you’re planning to travel alone, with your better half or a group of family members, Vrbo will help you find a vacation rental that fits your style with all the conveniences you’re looking for.
Are there large group vacation rentals in Oakes Estates?
Oakes Estates has four vacation rentals that can cater to 10 or more people. These properties come with the privacy and space you need to share good times with family and friends.
Are there vacation rentals in Oakes Estates that welcome kids?
Bring the entire family together for a fun-packed adventure in Oakes Estates at one of our 14 family-friendly vacation homes. These stays offer conveniences that are ideally suited to trips with the kids, like kitchens, multiple bedrooms and entertainment areas. Simply check the “Properties good for families” filter and choose your favorite option.
What are the top attractions for families in Oakes Estates?
There are plenty of exciting things to do and see with the family in Oakes Estates, including:

  • Vanderbilt Beach
  • Barefoot Beach
  • Naples Zoo at Caribbean Gardens

Are there one-bedroom vacation rentals in Oakes Estates?
Yes, you can take your pick from four one-bedroom rentals in Oakes Estates. Whether you’re searching for a comfy cottage or a fancy condo, our one-bedroom properties are perfect if you don’t need lots of space. One of the perks of having your own digs? You won’t need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Oakes Estates?
Choose from four two-bedroom vacation rentals in Oakes Estates. Put the kids in the second room or fill it with a couple of your best friends. There’s space for whoever’s fortunate enough to be joining in on the fun.
Are there vacation rentals with WiFi in Oakes Estates?
Whether you want to keep up with the latest news, reply to emails or update your social media accounts, there are five vacation homes with WiFi in Oakes Estates. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Oakes Estates?
Pick your travel dates and then use the filters to view vacation rentals with ac in Oakes Estates on Vrbo. With 14 air-conditioned properties on offer here, you can look forward to a cool and comfortable break.
How old do you have to be to rent a vacation rental in Oakes Estates?
You should check with the Oakes Estates vacation property you’re looking at on Vrbo as the age limit differs. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Oakes Estates for?
The amount of time you can book an Oakes Estates vacation rental for is down to each property. Just put in your travel dates to browse available options offering extended stays. They include the things you need to make your extended break more enjoyable and comfortable, like kitchens and yards. Some Vrbo vacation rentals may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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