Discover Your Perfect Great Diamond Island Rentals by Owner

Great Diamond Island Rentals by Owner

|
10.0 (1 Review)
Apartment
Monument Garden SWEET
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
10.0 (1 Review)
House
Pearl of Portland
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
View Availability
|
9.5 (108 Reviews)
House
Best Bower
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
More Top-Rated Rentals by Owner in Great Diamond Island Area

Why Choose Rent By Owner for your Great Diamond Island 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.

Best Times to Visit Great Diamond Island

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider visiting during the region’s shoulder seasons when accommodations are more available and the area offers a peaceful retreat away from peak crowds.

Peak Season Highlights

spring
June to August

During the summer months, you can enjoy the warmest weather and longest daylight hours, making it ideal for outdoor activities and seaside relaxation.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
spring
September to October

Early fall brings mild temperatures and fewer crowds, providing a serene setting to experience the area's natural beauty while still enjoying pleasant weather.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

image
November to February

Winter offers a quieter atmosphere with cooler temperatures, perfect for those seeking tranquility and scenic winter views in this region.

Average Temperature Daytime: 30°F to 45°F - Nighttime: 20°F to 30°F
image
March to May

Springtime ushers in milder weather and blooming scenery, providing a peaceful retreat before the busy summer season begins.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Great Diamond Island

How to Book Your Great Diamond Island 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 Great Diamond Island

More Top-Rated Rentals by Owner in Great Diamond Island 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

  • Enjoy access to private or shared outdoor decks with scenic views of the surrounding waters.
  • Take advantage of well-maintained outdoor grills for preparing meals during your stay.
  • Relax in inviting outdoor seating areas designed for socializing or peaceful contemplation.
  • Benefit from direct access to beaches or waterfronts for swimming, kayaking, or paddleboarding.
  • Utilize outdoor fire pits perfect for cozy evenings and marshmallow roasting under the stars.
  • Explore nearby walking trails or nature paths that offer a glimpse of the area's natural beauty.
  • Make the most of parking spaces suitable for boats or other watercraft, enhancing your adventure here.

Top Attractions Around Great Diamond Island

What attractions are nearby?

During your stay, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic walking trails that showcase the natural beauty of the region surrounding your rental by owner.

image
image

Family Activities

  • Exploring the beaches: Enjoy family walks and sandcastle building along the scenic shores that define this charming island destination.
  • Bird watching at local preserves: Observe a variety of native bird species in their natural habitat, making it an educational experience for children here.
  • Boating excursions: Take advantage of nearby boat rentals to explore the waters around the island and discover hidden coves and scenic views.
  • Nature walks and hiking trails: Discover the region’s lush landscapes and diverse flora on easy trails perfect for family outings here.
image

Adult Activities

  • Kayaking Adventures: Explore the scenic coastline of this destination by renting a kayak and enjoying peaceful paddling along the pristine waters.
  • Birdwatching Tours: Discover a variety of bird species native to the region on guided tours that take you through this area's protected natural habitats.
  • Beach Relaxation and Sunbathing: Unwind at the tranquil beaches, perfect for soaking up the sun and enjoying the serene seaside atmosphere.
  • History and Nature Walks: Take a self-guided or guided walk to learn about the area's maritime history while experiencing the natural beauty of the coastal landscape.

Great Diamond Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Transportation: Arrange your ferry or boat transfers in advance to ensure seamless arrivals and departures while enjoying the natural beauty of this destination.
  • Explore Off-the-Beaten-Path Areas: Take time to discover lesser-known spots around the region to experience a more authentic and serene side of the island life here.
  • Embrace Water Activities: Make the most of the area’s coastal location by engaging in kayaking, sailing, or fishing, which are perfect ways to immerse yourself in this region’s maritime charm.
  • Respect the Local Environment: Follow eco-friendly practices during your stay to help preserve the natural beauty that makes this destination so special for visitors seeking tranquility and outdoor adventure.

Transportation Options

  • Ferry Services: Regular ferry trips connect the island to Portland and other coastal points, providing a scenic and convenient way to arrive or depart.
  • Private Boat Rentals: You can opt for renting a private boat to explore the region at your own pace, enjoying the privacy and flexibility of your island adventure.
  • Water Taxis: Water taxis offer quick and flexible transportation options around the area, ideal for spontaneous trips or short excursions.
  • Car Rentals on the Mainland: While vehicles are not available directly on the island, arranging a car rental from nearby Portland makes exploring the surrounding region effortless.

Local Customs Options

  • Respect for Local Maritime Traditions: You should observe the island's longstanding maritime customs, including proper boating etiquette and honoring local fishing practices.
  • Environmental Preservation Practices: It’s important to adhere to eco-friendly behaviors like waste disposal and respecting wildlife to help preserve the area's natural beauty.
  • Community Gathering Etiquette: Participating in local gatherings or events requires a respectful attitude and understanding of the community’s informal social norms.
  • Respect for Historic Sites: When exploring the region’s historical spots, ensure you follow guidelines to preserve the heritage sites for future visitors.

Frequently Asked Questions About Great Diamond Island Rentals by Owner

1. What are the top vacation rentals in Great Diamond Island?

There are a lot of options in Great Diamond Island. If you plan on staying in the Great Diamond 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 Great Diamond Island:

2. How many Rentbyowner vacation rentals are available in Great Diamond Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 208 in the Great Diamond 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 Great Diamond Island. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary among listings on Rent By Owner. You should review the specific property's cancellation terms directly on the listing or contact the owner for detailed information before booking.

4. How do I verify the legitimacy of a rental by owner in this region?

Rent By Owner provides verified listings and host profiles to ensure trustworthiness. To further confirm, read reviews and reach out to the property owner with any questions regarding the rental.

5. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning fees, service charges, or security deposits are typically specified in the listing details. It’s best to review the property’s total cost breakdown or contact the owner for clarification.

6. What amenities are usually included in rentals by owner in this destination?

Amenities can vary, but many rentals in this region offer essentials like Wi-Fi, kitchen facilities, and outdoor spaces. Check each listing for a full list of included amenities to ensure it meets your needs.

7. How far in advance should I book a rental by owner in this region during peak season?

To secure your preferred dates, especially during busy periods, it’s recommended to book several months in advance. Availability can vary, so early reservations help guarantee your stay.

More Rentals You May Like Near Great Diamond Island

More Top-Rated Rentals by Owner in Great Diamond Island Area