1. USA
  2. Maryland
  3. Isle of Wight
  4. Rentals by Owner

Discover Your Perfect Isle of Wight Rentals by Owner

Isle of Wight Rentals by Owner

|
9.2 (111 Reviews)
Apartment
Saint Tropez
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Isle of Wight Area

Why Choose Rent By Owner for your Isle of Wight vacation rental?

What makes our Rentals by Owner special?

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

Popular Areas for Isle of Wight Rentals by Owner

Where are the best neighborhoods to stay in Isle of Wight?

When choosing where to stay in Isle of Wight, Maryland, you’ll find a variety of charming neighborhoods that cater to different preferences. Whether you're seeking a quiet retreat or a lively community, the local areas offer convenient access to the region’s natural beauty and local amenities. By booking a rental by owner through Rent By Owner, you can enjoy a seamless experience in selecting the perfect neighborhood that fits your travel plans. Each neighborhood provides a unique atmosphere, ensuring you find a comfortable and authentic stay in Isle of Wight, Maryland.

Ocean Pines

Located just outside the historic town of Berlin, this area offers a peaceful retreat with easy access to local beaches and outdoor activities. It’s an ideal choice for travelers seeking a relaxing stay in Maryland with the convenience of nearby amenities.

View 316+ Rentals in Ocean Pines

Best Times to Visit Isle of Wight

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here ensures you experience the area's natural beauty and local charm at its best, making your Rent By Owner stay in Isle of Wight, Maryland, unforgettable and perfectly tailored to your preferences.

Peak Season Highlights

summer
Summer (June - August)

During the summer months, you'll experience warm weather ideal for outdoor activities and enjoying the scenic views that this destination offers.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
autumn
Fall (September - October)

Early fall provides pleasant temperatures and fewer crowds, making it a great time to explore without the peak-season rush in this region.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 55°F to 60°F

Off-Season Highlights

image
Winter (December - February)

The winter season sees cooler temperatures and quieter surroundings, perfect if you prefer a peaceful retreat away from busy periods.

Average Temperature Daytime: 45°F to 50°F - Nighttime: 30°F to 35°F
image
Spring (March - May)

Spring offers mild weather with blooming scenery, providing an ideal opportunity for exploring comfortably before the summer influx begins.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Isle of Wight

How to Book Your Isle of Wight vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Isle of Wight

More Top-Rated Rentals by Owner in Isle of Wight Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

  • You can enjoy a private outdoor space with a patio or deck, perfect for relaxing or entertaining during your stay.
  • Expect to find a barbecue grill available for outdoor cooking and family cookouts.
  • Many rentals offer spacious yards or gardens where you can unwind amidst nature.
  • A community pool or shared swimming area is often accessible nearby, providing a refreshing escape.
  • Look for outdoor fire pits or fireplaces ideal for cozy evenings under the stars.
  • Some properties feature direct access to nearby beaches or waterfront areas for water-based activities.
  • Outdoor recreational amenities like tennis courts, volleyball nets, or walking trails are commonly available in the region.

Top Attractions Around Isle of Wight

What attractions are nearby?

In this region, you can enjoy a variety of outdoor activities and local attractions that allow you to explore the natural beauty and cultural charm of the area while staying comfortably in your rental by owner.

image
image

Family Activities

  • Isle of Wight Family Fun Park: Enjoy a day exploring this local amusement park, perfect for kids and adults to experience classic rides and engaging activities in the area.
  • Nature Walks at Island Trails: Discover scenic walking trails nearby that offer an enjoyable outdoor adventure for families seeking a relaxing way to explore the region’s natural beauty.
  • Beach Activities at Wight Beach: Spend quality time relaxing on the sandy shores while building sandcastles or soaking up the sun with your loved ones along this popular coastline.
  • Visit to the Local Farm: Experience farm life through interactive activities and animal encounters, making it an educational and entertaining outing for children visiting here.
image

Adult Activities

  • Wine Tastings at Local Vineyards: Explore the region’s renowned wineries for tastings and tours that showcase the area's rich viticulture.
  • Golfing at Scenic Courses: Enjoy a round of golf on beautifully maintained courses that offer stunning views and challenging play in the area.
  • Sailing and Water Sports: Take advantage of the local waterways with sailing, kayaking, or paddleboarding, perfect for outdoor enthusiasts seeking adventure.
  • Historic Sites and Museums: Discover the history of this destination through its well-preserved historic sites and engaging museums, providing cultural enrichment during your stay.

Isle of Wight Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's calendar to align your stay with local festivals or community events, enhancing your experience in this region.
  • Explore Natural Attractions: Take advantage of nearby parks and water bodies to enjoy outdoor activities that showcase the natural beauty here.
  • Utilize Nearby Amenities: Make the most of local shops, markets, and eateries to immerse yourself in the region’s culture during your visit.
  • Communicate with Your Host: Reach out to your rental owner to get personalized tips on hidden gems and must-see spots in this destination.

Transportation Options

  • Car Rentals: Renting a car offers the flexibility to explore the region at your own pace and visit attractions around this area comfortably.
  • Public Transit: Bus services provide an economical and convenient way to navigate through the local surroundings without the hassle of parking.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber or Lyft are readily available, offering quick transportation within the destination.
  • Biking: Cycling is an eco-friendly option that allows you to enjoy the scenic views and get some exercise while exploring here.

Local Customs Options

  • Respect for Local History: Embrace the area's deep-rooted history by participating in community events and honoring local landmarks during your stay.
  • Community Engagement: Engage with residents through traditional gatherings and local markets to experience the region's authentic cultural vibe.
  • Environmental Conservation: Practice eco-friendly habits, such as recycling and conserving water, to preserve the natural beauty that attracts visitors here.
  • Celebration of Seasonal Festivals: Join in seasonal festivities that highlight the region’s unique traditions, offering a genuine glimpse into local customs during your visit.

Frequently Asked Questions About Isle of Wight Rentals by Owner

1. What are the top vacation rentals in Isle of Wight?

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

2. How many Rentbyowner vacation rentals are available in Isle of Wight?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2150 in the Isle of Wight 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 Isle of Wight. 

3. What is the cancellation policy for rental properties in this area?

Cancellation policies vary by listing. You should review the specific terms on the property page or contact the owner directly to understand the cancellation options and any applicable fees before booking.

4. How do I communicate with the property owner during my stay?

You can reach out to the owner through the messaging system provided on the booking platform. For questions or special requests, contacting the owner in advance ensures a smooth stay.

5. Are there any specific check-in and check-out procedures I should be aware of?

Check-in and check-out procedures are detailed on each listing. It’s advisable to review these details prior to arrival or contact the owner if you need further clarification for your stay here.

6. What amenities are typically included in rental properties in this region?

Most rentals by owner offer essential amenities such as Wi-Fi, kitchen facilities, and parking. To see what’s included in a particular property, please refer to the listing description or ask the owner directly.

7. Is it possible to modify my reservation after booking in this destination?

Modifications depend on the individual owner’s policies. You should review the terms on your reservation or contact the property owner to request changes, ensuring you adhere to their guidelines.

More Rentals You May Like Near Isle of Wight

More Top-Rated Rentals by Owner in Isle of Wight Area