Discover Your Perfect Little Diamond Island Vacation Homes

Best Vacation Homes in Little Diamond Island

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10.0 (2 Reviews)
Apartment
Morning on the Atlantic
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
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9.6 (152 Reviews)
Bed & Breakfast
Blind Tiger Portland - Danforth Street.
  • Air Conditioner
  • TV
  • Accessibility
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Why Choose Rent By Owner for your Little Diamond 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 Little Diamond Island Vacation Rentals

Where are the best neighborhoods to stay in Little Diamond Island?

Nestled within the charming surroundings of Little Diamond Island, Portland, Maine, offers a unique and tranquil setting for your next getaway. This peaceful neighborhood provides a perfect escape from the hustle and bustle, allowing you to enjoy the serene coastal atmosphere while remaining close to the vibrant attractions of Portland. Whether you're seeking a cozy retreat or a comfortable base for exploring the area, staying in this neighborhood ensures an authentic Maine experience with convenient access to beautiful waterfront views and local amenities. Discover ideal vacation rentals that match your needs and make your stay on Little Diamond Island truly memorable.

Downtown Portland

Staying in downtown Portland offers easy access to the city's vibrant attractions and cultural scene, making it an ideal base for exploring this destination's diverse offerings.

View 139+ Rentals in Downtown Portland

Old Port

This historic neighborhood is known for its charming cobblestone streets and lively waterfront, providing a perfect setting for experiencing the region’s maritime charm.

View 57+ Rentals in Old Port

Pine Point

Situated along the coast, Pine Point provides tranquil seaside views and easy access to Maine’s beautiful beaches, ideal for relaxing getaways.

View 60+ Rentals in Pine Point

Parkside

Close to parks and green spaces, Parkside offers a peaceful retreat with convenient access to local amenities in the heart of the city.

View 45+ Rentals in Parkside

West End

Known for its historic architecture and tree-lined streets, the West End is a charming neighborhood perfect for those seeking a blend of culture and elegance.

View 60+ Rentals in West End

Munjoy Hill

Perched atop a hill, this area boasts stunning views of the harbor and is close to popular local spots, making it a favorite among visitors.

View 69+ Rentals in Munjoy Hill

East End

With its scenic waterfront views and artsy vibe, the East End provides a picturesque and culturally rich environment for exploring the region.

View 69+ Rentals in East End

Ferry Village

Offering a quaint seaside atmosphere, Ferry Village is perfect for enjoying coastal walks and embracing the maritime traditions of this destination.

View 593+ Rentals in Ferry Village

Best Times to Visit Little Diamond Island

When should you plan your Vacation Rentals stay?

Knowing the best time to visit here can enhance your experience, allowing you to enjoy the region’s natural beauty and serene atmosphere at its peak during ideal seasons.

Peak Season Highlights

summer
Summer (June to August)

This is the most popular time to visit for warm weather and extended daylight hours, making it ideal for exploring the region’s scenic coastlines and outdoor activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Early Fall (September to October)

During this period, you can enjoy pleasant temperatures and fewer crowds, perfect for experiencing the area's natural beauty and tranquility.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Late Fall to Winter (November to February)

Visit during these months to experience quieter surroundings and lower prices while taking in the peaceful winter scenery of this destination.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Early Spring (March to May)

This is a less crowded period when you can witness the awakening of nature and enjoy more affordable accommodation options.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Little Diamond Island

How to Book Your Little Diamond 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 Little Diamond Island

More Top-Rated Vacation Rentals in Little Diamond 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 scenic outdoor spaces with private patios or decks perfect for relaxing amid the natural beauty of the area.
  • Take advantage of waterfront access, including private docks or boat slips for exploring the surrounding waters.
  • Make use of outdoor dining areas equipped with grills, ideal for enjoying meals outdoors in this charming destination.
  • Benefit from lush gardens or landscaped yards that provide peaceful spots for outdoor activities or gatherings.
  • Experience convenient parking areas designed to accommodate visitors exploring this region by car.
  • Utilize outdoor shower facilities, especially useful after a day spent on the nearby beaches or boating adventures.
  • Access shared outdoor amenities such as swimming pools or recreational areas, offering additional entertainment options here.

Top Attractions Around Little Diamond Island

What attractions are nearby?

When staying here, you can enjoy exploring nearby scenic walking trails, relaxing at tranquil beaches, and experiencing the local maritime activities that make this destination a charming coastal getaway.

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Family Activities

  • Beach Exploration: Spend a relaxing day enjoying the sandy shores, ideal for building sandcastles and swimming in the calm waters of the region.
  • Kayaking Adventures: Discover the scenic coastline by renting kayaks and paddling along the tranquil waters surrounding the island.
  • Wildlife Watching: Observe local bird species and marine life that thrive in this destination’s natural habitats, offering educational fun for the whole family.
  • Picnic at the Park: Pack a meal and unwind at charming park areas perfect for family picnics amidst the area's stunning views.
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Adult Activities

  • Kayaking and Paddleboarding: Take advantage of the calm waters surrounding this destination by exploring the coastline through kayaking or paddleboarding, offering both relaxation and adventure.
  • Fishing Expeditions: Engage in a fishing excursion in the region's abundant waters, ideal for experiencing local marine life and enjoying a tranquil day on the water.
  • Sailing Tours: Embark on a sailing tour to appreciate scenic views and learn about the area's maritime history from experienced captains.
  • Beachcombing and Coastal Walks: Stroll along the shoreline to discover unique shells and enjoy breathtaking seaside vistas that highlight this destination’s natural beauty.

Other Places to Stay in Little Diamond Island, ME

Sand Beach
Sand Beach Vacation Rentals
Fort Gorges
Fort Gorges Vacation Rentals
More Places to Stay Near Little Diamond Island

Little Diamond Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Remote Access: Take advantage of the island's peaceful surroundings by packing essential supplies and planning your ferry or boat transportation in advance to ensure a smooth arrival and departure.
  • Explore Local Water Activities: Make the most of the destination's scenic waterways by booking kayaking, sailing, or paddleboarding activities that allow you to enjoy the natural beauty right from your doorstep.
  • Choose a Scenic Spot for Relaxation: Select a vacation rental with waterfront views or easy access to the beach to unwind while soaking in the picturesque surroundings.
  • Discover Nearby Dining Options: While here, explore local eateries or prepare fresh seafood in your rental’s kitchen to experience authentic regional flavors in a cozy setting.

Transportation Options

  • Ferry Service: A popular way to reach this destination, the ferry service offers scenic crossings that provide lovely views of the surrounding waters.
  • Private Boat Charters: For a more personalized experience, private boat charters can be arranged to transport you directly to your vacation rental on the island.
  • Water Taxis: Water taxis serve as a quick and convenient transportation option, connecting the area to Portland’s mainland for easy access to amenities.
  • Personal Vehicles and Biking: Once here, exploring by bike or car allows you to enjoy the peaceful surroundings and reach your rental comfortably.

Local Customs Options

  • Respect for Maritime Traditions: Locals take pride in their maritime history, and visitors are encouraged to observe traditional fishing practices and boat customs that have been part of the area's culture for generations.
  • Environmental Stewardship: Preserving the natural beauty of this island community is important, so residents often participate in eco-friendly practices like shoreline cleanup and responsible boating to protect local ecosystems.
  • Community Gatherings: Participating in seasonal events and gatherings held on the island reflects the close-knit spirit here and offers insight into the region's welcoming customs.
  • Respect for Privacy and Space: Given the serene setting, locals value quiet and respect for personal space, making it considerate to keep noise levels low and honor property boundaries during your stay.

Frequently Asked Questions About Little Diamond Island?

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 529 in the Little 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 Little Diamond Island. 

3. What is the cancellation policy for booking a vacation rental on Little Diamond Island?

The cancellation policy varies depending on the specific property, so it is best to review the listing details or contact the owner directly to understand the terms and any potential fees.

4. How do I confirm availability for my desired dates in this island destination?

Availability can be checked by reviewing the calendar on the property listing. For confirmation, reaching out directly to the host ensures you receive up-to-date information about your preferred travel period.

5. Are there any specific amenities or features I should be aware of before booking?

Each vacation rental offers different amenities. To ensure the property meets your needs, carefully read the listing description and amenities section or contact the host for additional details.

6. What should I know about the check-in and check-out procedures for stays here?

Check-in and check-out instructions are typically provided in the listing or sent directly by the host. It's recommended to review these details ahead of time to ensure a smooth arrival and departure process.

7. Is there parking available near the vacation rentals on the island?

Parking options vary by property. Some rentals may include designated parking spots, while others might require street parking or arrangements with local facilities. Confirm specifics directly with the property owner during booking.

Best Vacation Homes in Little Diamond Island

|
10.0 (1 Review)
Apartment
Monument Garden SWEET
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability