Discover Your Perfect Oak Island Vacation Homes

Oak Island Large Vacation Homes

See More Family Vacation Rentals in Oak Island on FVR

Why Choose Rent By Owner for your Oak Island Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Oak Island Vacation Rentals

Where are the best neighborhoods to stay in Oak Island?

When planning your stay in Oak Island, Kissimmee, Florida, choosing the right neighborhood can greatly enhance your vacation experience. Each area offers unique charm and convenient access to local attractions, making it easier for you to enjoy everything this vibrant destination has to offer. Whether you're seeking a lively community close to entertainment or a more relaxed setting nestled near natural parks, you'll find options that suit your preferences. Exploring neighborhoods within Oak Island and Kissimmee ensures you select a location that aligns perfectly with your travel plans, providing comfort, accessibility, and a memorable stay in this popular Florida destination.

West Kissimmee

This area offers convenient access to the region's major attractions, making it an ideal choice for travelers seeking comfort and convenience in their vacation rentals. Stay here to enjoy a peaceful environment with easy connectivity to the vibrant sights of Kissimmee.

View 20628+ Rentals in West Kissimmee

Best Times to Visit Oak Island

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, with each season offering unique advantages for enjoying the region’s welcoming atmosphere and local charm.

Peak Season Highlights

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Winter (December to February)

During the winter months, you can enjoy the warm climate and lively atmosphere at this destination in Florida, making it ideal for a winter getaway.

Average Temperature Daytime: mid-70s°F - Nighttime: mid-50s°F
summer
Summer (June to August)

The summer season offers hot weather and longer days, perfect for outdoor activities and enjoying the region's sunny beaches.

Average Temperature Daytime: high-80s°F to low-90s°F - Nighttime: mid-70s°F

Off-Season Highlights

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Spring (March to May)

In spring, the area experiences pleasant temperatures and less crowded conditions, providing a more relaxed vacation experience.

Average Temperature Daytime: mid-70s°F to low-80s°F - Nighttime: mid-50s°F to mid-60s°F
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Fall (September to November)

Fall brings comfortable weather and fewer visitors, making it an excellent time to explore and enjoy the region’s natural beauty.

Average Temperature Daytime: high-70s°F - Nighttime: mid-50s°F

Weekly Weather Forecast for Oak Island

How to Book Your Oak Island 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 Oak Island

More Top-Rated Vacation Rentals in Oak Island Area

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 access to a private outdoor swimming pool, perfect for relaxing under the Florida sun.
  • Make the most of your stay with a well-maintained outdoor patio or deck area for gatherings and dining al fresco.
  • Take advantage of a lush, landscaped yard ideal for outdoor activities or simply unwinding outdoors.
  • Benefit from on-site outdoor parking facilities to conveniently accommodate your vehicle during your visit.
  • Discover shaded areas or gazebos that provide relief from the heat while enjoying the fresh air.
  • Utilize convenient outdoor grilling stations or BBQ pits for fun cookouts with family and friends.
  • Explore nearby outdoor recreational spaces or walking trails available within the community or local vicinity.

Top Attractions Around Oak Island

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of activities nearby, from exciting outdoor adventures to family-friendly attractions, all easily accessible when you stay in the area’s comfortable vacation rentals.

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Family Activities

  • Fun Spot America Theme Park: Enjoy a day of thrill rides, family-friendly attractions, and go-kart racing at this popular amusement park in the region.
  • Medieval Times Dinner & Tournament: Experience an entertaining medieval-style show complete with jousting, horsemanship, and a hearty feast suitable for all ages.
  • Old Town Kissimmee: Explore this historic shopping and entertainment district offering classic American fun, live entertainment, and vibrant nightlife options.
  • Kissimmee Lakefront Park: Relax and unwind with scenic waterfront views, playgrounds, and picnic areas perfect for family outings in the area.
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Adult Activities

  • Windsor Hills Golf Club: Test your skills and enjoy a relaxing day on the scenic courses designed for golf enthusiasts visiting the area.
  • Old Town Kissimmee: Experience the vibrant atmosphere with classic car shows, shopping, and entertainment, perfect for adult outings in this lively destination.
  • Local Dining Experiences: Savor Florida’s culinary diversity at the many restaurants offering everything from casual bites to fine dining, all within easy reach.
  • Watersports and Boating: Explore the nearby lakes and waterways with kayaking, paddleboarding, or boat rentals, ideal for outdoor adventure seekers in the region.

Oak Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Attractions: Take the time to explore nearby attractions and activities to maximize your stay in this region's vibrant community and entertainment options.
  • Choose a Strategically Located Property: Select vacation rentals that are conveniently situated near key destinations, making it easier to enjoy everything here without lengthy commutes.
  • Utilize Local Dining and Shopping Options: Immerse yourself in the area's culinary scene and shopping districts to get a true taste of the local culture during your visit.
  • Take Advantage of the Climate: Make the most of the warm weather by scheduling outdoor activities and relaxing at your rental's private amenities when the weather is ideal.

Transportation Options

  • Car Rentals: Conveniently explore the area with a variety of local car rental services available just minutes from here, offering flexible options to suit your travel needs.
  • Shuttle Services: Reliable shuttle services operate regularly between the destination and major airports, ensuring a smooth start and end to your stay in this region.
  • Taxi and Rideshare: Easily hail taxis or book rides through popular rideshare apps for quick, direct transportation around the area at any time.
  • Public Transit: Local buses provide an economical way to navigate here, connecting you to key attractions and amenities within the community.

Local Customs Options

  • Local Festivals and Events: Throughout the year, you'll find vibrant celebrations that showcase the area's rich cultural heritage and community spirit.
  • Respect for Nature and Environment: The region values its natural beauty, encouraging visitors to practice eco-friendly habits and conservation efforts during their stay.
  • Food and Dining Etiquette: Embracing local flavors is common here, with a friendly approach towards trying regional specialties and supporting small businesses.
  • Southern Hospitality: Warm welcomes and courteous interactions define the local customs, making every visitor feel at home during their visit to this destination.

Frequently Asked Questions About Oak Island?

1. What are the top vacation rentals in Oak Island?

There are a lot of options in Oak Island. If you plan on staying in the Oak Island area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oak Island:

2. How many vacation rentals have private pools in Oak Island?

There are 11117 vacation rentals with private pools near Oak Island. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Oak Island are best for families?

If you are looking for a family-friendly vacation home in Oak Island, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oak Island:

4. How many Rentbyowner vacation rentals are available in Oak Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 23620 in the Oak Island 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 Oak Island. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property listing. To understand the specific terms, please review the cancellation policy outlined in the individual rental listing or contact the property owner directly.

6. Are there any additional fees I should be aware of when booking a vacation rental in this destination?

Additional fees such as cleaning fees, service charges, or taxes are typically specified in the listing details. Be sure to review all fee information before completing your booking to avoid surprises.

7. How do I secure my reservation and what payment methods are accepted?

Reservations are secured through the booking platform with the payment methods specified by the property owner. Common options include credit cards and online payment services. Details are provided during the booking process.

8. Can I find vacation rentals with flexible check-in and check-out times?

Flexibility regarding check-in and check-out times varies by property. It's best to communicate your preferences with the host during booking to confirm available options.

9. What amenities are typically included with vacation rentals here?

Most properties offer amenities such as Wi-Fi, kitchen facilities, air conditioning, and private parking. For a complete list of amenities, consult the individual property description or contact the host directly.

Oak Island Top Rated Vacation Rentals

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