Best Vacation Homes in Oakes Estates
House
4 Bedrooms
2 Baths
6 Guests
Private Pool
Fireplace/Heating
Pool
Ocean View
US $395/Night
7 Nights - US $2,765
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
32291.73 ft²
Oceanfront
Hot Tub
Spa- Pool
US $695/Night
7 Nights - US $4,865
Hotel
9.4(911 Reviews)
1 Bath
- Pool
Balcony/Terrace
Breakfast
Kitchen
US $114/Night
7 Nights - US $797
Apartment
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
Pet Friendly
Air Conditioner
Internet
US $114/Night
7 Nights - US $796
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
1829.86 ft²
- Oceanfront
- Pool
- Ocean View
View
US $445/Night
7 Nights - US $3,113
Apartment
10.0(87 Reviews)
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $174/Night
7 Nights - US $1,217
House
10.0(52 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $273/Night
7 Nights - US $1,910
Apartment
10.0(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
Parking- Air Conditioner
US $249/Night
7 Nights - US $1,743
Oakes Estates Luxury Rentals
House
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
Unlock the Best Price
Apartment
8.7(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1280.91 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $3,000/Night
7 Nights - US $21,000
Apartment
8.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1227.09 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $2,550/Night
7 Nights - US $17,850
House
10.0(7 Reviews)
8 Bedrooms
6 Baths
20 Guests
9500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $2,109/Night
7 Nights - US $14,763
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $2,088/Night
7 Nights - US $14,619
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,303/Night
7 Nights - US $9,118
House
9.8(20 Reviews)
6 Bedrooms
4 Baths
16 Guests
4000 ft²
- Private Pool
- Oceanfront
- Spa
- Fireplace/Heating
US $1,254/Night
7 Nights - US $8,780
House
10.0(7 Reviews)
3 Bedrooms
2 Baths
10 Guests
3000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,160/Night
7 Nights - US $8,120
Oakes Estates Pet Friendly Vacation Rentals
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $251/Night
7 Nights - US $1,756
Resort
9.5(31 Reviews)
16 Baths
79 Guests
558.74 ft²
Private Beach- Oceanfront
- Hot Tub
- Spa
US $411/Night
7 Nights - US $2,877
US $575/Night
7 Nights - US $4,027
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $174/Night
7 Nights - US $1,217
House
9.0(4 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $575/Night
7 Nights - US $4,028
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1449 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $394/Night
7 Nights - US $2,761
Apartment
9.8(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $227/Night
7 Nights - US $1,592
House
9.6(39 Reviews)
1 Bedroom
1 Bath
3 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $139/Night
7 Nights - US $971
Oakes Estates Large Vacation Homes
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $127/Night
7 Nights - US $889
House
4.0(1 Review)
5 Bedrooms
4 Baths
9 Guests
4305.56 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $700/Night
7 Nights - US $4,900
Villa
9.4(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $139/Night
7 Nights - US $974
US $1,084/Night
7 Nights - US $7,585
Villa
9.4(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $169/Night
7 Nights - US $1,182
Villa
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $273/Night
7 Nights - US $1,910
Villa
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $269/Night
7 Nights - US $1,884
Villa
2 Bedrooms
2 Baths
6 Guests
2050 ft²
- Spa
- Fireplace/Heating
- Pool
- Kitchen
US $265/Night
7 Nights - US $1,854
Why Choose Rent By Owner for your Oakes Estates Vacation Rental Homes?
What makes our Vacation Rentals special?
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Book with confidence knowing every property meets our quality and safety standards.
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Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Oakes Estates Vacation Rentals
Where are the best neighborhoods to stay in Oakes Estates?
When choosing where to stay in Naples, Florida, Oakes Estates offers a peaceful and convenient neighborhood that caters to those seeking a relaxed yet accessible location. This area provides easy access to local amenities and outdoor spaces, making it an ideal spot for your next getaway. Whether you're exploring the vibrant community or simply relaxing in your comfortable vacation rental, staying in Oakes Estates ensures you experience the best of Naples' welcoming atmosphere. Discover the perfect place to unwind while remaining close to the natural beauty and attractions that make this region special.
Tarpon Bay
In this part of Naples, you can enjoy the tranquility of a peaceful neighborhood while remaining close to the region's best amenities. It's an ideal choice for those seeking a relaxing stay in a scenic area with easy access to local attractions.
View 685+ Rentals in Tarpon BayBest Times to Visit Oakes Estates
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit ensures you can fully enjoy the relaxed atmosphere and pleasant weather that make this destination a popular choice for travelers seeking memorable getaways in the region.
Peak Season Highlights
Winter (December to February)
During the winter months, this region experiences peak attractiveness due to warm and pleasant weather, making it an ideal time for enjoying outdoor activities and relaxing at your holiday home.
Average Temperature Daytime: 75°F to 80°F - Nighttime: 55°F to 65°F
Spring (March to May)
Spring marks another high season here when the scenic beauty blooms, attracting visitors looking to experience the region’s vibrant atmosphere and comfortable climate.
Average Temperature Daytime: 78°F to 85°F - Nighttime: 60°F to 68°F
Off-Season Highlights
Summer (June to August)
The summer months see a slight dip in visitors, offering a more relaxed environment with hotter days perfect for indoor retreats or early morning excursions.
Average Temperature Daytime: 88°F to 92°F - Nighttime: 70°F to 75°F
Fall (September to November)
Autumn is considered off-peak as the temperatures begin to cool, providing a quieter experience for those seeking tranquility and less crowded vacation rentals here.
Average Temperature Daytime: 83°F to 86°F - Nighttime: 65°F to 73°F
Weekly Weather Forecast for Oakes Estates
How to Book Your Oakes Estates Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Oakes Estates
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private swimming pool to relax and unwind outdoors.
- Take advantage of spacious outdoor patios with comfortable seating areas.
- Utilize outdoor dining spaces ideal for enjoying meals under the sun.
- Make the most of lush landscaped gardens that provide privacy and natural beauty.
- Relax in shaded pergolas or gazebos designed for outdoor entertaining.
- Benefit from outdoor grilling stations perfect for cookouts with family and friends.
- Explore nearby walking or biking paths to experience the scenic surroundings of this region.
Top Attractions Around Oakes Estates
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities and explore local parks, providing a perfect blend of relaxation and adventure during your stay.
Family Activities
- Naples Zoo at Caribbean Gardens: Spend a day exploring diverse wildlife exhibits and interactive encounters that delight children and adults alike in this family-friendly attraction nearby.
- Golisano Children’s Museum of Naples: Engage the young ones with hands-on exhibits designed to spark creativity and learning within a vibrant educational environment close to here.
- Lighthouse Beach Park: Enjoy relaxing on pristine sands and building sandcastles while soaking up the sunshine at this scenic spot along the Gulf of Mexico.
- Clam Pass Park: Experience a fun, scenic stroll through mangroves to reach a beautiful beach where your family can swim, picnic, and unwind together.
Adult Activities
- Golfing at Tiburón Golf Club: Enjoy a day on the lush fairways of one of the region’s premier golf courses, perfect for both beginners and seasoned players.
- Exploring Naples Botanical Garden: Discover the vibrant plant collections and tranquil walking paths that highlight the natural beauty of this destination’s outdoor spaces.
- Fishing Adventures in the Gulf of Mexico: Embark on a fishing charter or cast a line from the nearby piers to experience the region’s renowned marine bounty.
- Spa and Wellness Centers: Indulge in relaxing treatments at local spas that offer rejuvenating experiences tailored for visitors seeking pampering in this area.
Oakes Estates Travel Tips
How Can You Make the Most of Your Stay?
- Arrive prepared to explore the natural beauty of the area: Take advantage of local outdoor activities by planning visits to nearby parks and scenic spots that highlight this destination’s lush landscape.
- Utilize nearby amenities to enhance your stay: Select a vacation rental that offers easy access to essential services and recreational facilities for a comfortable experience here.
- Plan your days around the region's prime weather conditions: Check the local forecast to make the most of sunny days and avoid heavy rainfall, optimizing your time exploring the area.
- Respect the local environment and community: Practice eco-friendly habits and be mindful of neighborhood rules to enjoy a harmonious visit in this popular destination.
Transportation Options
- Personal Vehicles: Renting or using your own car offers the most flexibility for exploring the local attractions and scenic areas around this part of Naples.
- Local Taxis and Ride-Sharing Services: Convenient transportation options like taxis and ride-sharing apps provide easy access to nearby shopping, dining, and entertainment venues.
- Public Transit: The regional bus system connects you efficiently with key destinations within the region, making it a budget-friendly choice during your stay.
- Rental Cars: Car rental services in the area allow for comfortable and convenient day trips while enjoying the warm Florida climate and coastal views.
Local Customs Options
- Southern Hospitality: You’ll notice residents often greet visitors warmly, reflecting the area's friendly and welcoming community spirit.
- Respect for Nature: Locals in this region place a high value on preserving the natural beauty, encouraging eco-friendly practices among visitors.
- Golf Etiquette: Since numerous golf courses are nearby, practicing good etiquette on the greens is appreciated by both locals and fellow visitors.
- Community Engagement: Participating in local events such as neighborhood gatherings helps you connect authentically with this destination's close-knit community.
Oakes Estates Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Oakes Estates?
There are a lot of options in Oakes Estates. If you plan on staying in the Oakes Estates area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oakes Estates:
- Private Suite on 3 Acres in North Naples!
- Modern North Naples Villa on 3 Acres!
- NEW Naples Modern Farmhouse w/Heated Pool, Sleep 10
- Villa Mango
- Lux Naples! Heated Pool ~ Fenced Yard ~ Near Beach
- Two Master Suites, Fully Stocked Home w/Heated Pool & Spa Close to Everything
- MODERN ELEGANT LUXURY HOME - Airy, uncluttered, clean & peaceful
- The Secret Garden
- Naples Beach , Golf and Country Club Naples Florida
- Modern 3BR Naples retreat with private pool & hot tub, near beaches. Bonus: Miami World Cup matches just a scenic drive away.
2. How many vacation rentals have private pools in Oakes Estates?
There are 108 vacation rentals with private pools near Oakes Estates. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Oakes Estates are best for families?
If you are looking for a family-friendly vacation home in Oakes Estates, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oakes Estates:
4. How many Rentbyowner vacation rentals are available in Oakes Estates?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 615 in the Oakes Estates area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oakes Estates.
5. What is the cancellation policy for booking a vacation rental in Oakes Estates?
The cancellation policy varies between individual properties. To understand the specific terms and potential refund options, it's best to review the listing details or contact the property owner directly.
6. How do I confirm my reservation at a vacation rental in this area?
Reservation confirmation typically occurs after completing the booking process and receiving a confirmation email. For any additional questions or special requests, reaching out to the property owner can ensure a smooth reservation.
7. Are there any house rules I should be aware of when staying in these vacation rentals?
Each property has its own set of house rules outlined in the listing. It’s important to review these before booking and communicate with the host if you have any questions about policies such as pet accommodations, smoking, or guest limits.
8. What amenities are usually included in vacation rentals in this region?
Amenities often vary but commonly include essentials like Wi-Fi, kitchen access, and parking. For specific features such as pools or outdoor spaces, check the individual listing details or contact the owner directly.
9. How close are the vacation rentals to local attractions or beaches?
Most rentals are conveniently located within a short drive to popular destinations and beaches in the area. To find properties that meet your proximity preferences, review the location details on each listing or inquire with the host.
Oakes Estates Top Rated Vacation Rentals
House
10.0(37 Reviews)
4 Bedrooms
3 Baths
12 Guests
2150 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $570/Night
7 Nights - US $3,990
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $249/Night
7 Nights - US $1,741
House
10.0(15 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $503/Night
7 Nights - US $3,522
House
10.0(14 Reviews)
3 Bedrooms
2 Baths
5 Guests
2080 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $430/Night
7 Nights - US $3,011
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $163/Night
7 Nights - US $1,144
Condo
10.0(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $143/Night
7 Nights - US $999
House
10.0(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
1825 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $398/Night
7 Nights - US $2,788
Apartment
10.0(11 Reviews)
3 Bedrooms
2 Baths
10 Guests
1535 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $267/Night
7 Nights - US $1,866
