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  2. Maine
  3. Portland
  4. Monument Square
  5. Rentals by Owner

Discover Your Perfect Monument Square Rentals by Owner

Monument Square Rentals by Owner

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10.0 (1 Review)
Apartment
Monument Garden SWEET
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Monument Square Area

Why Choose Rent By Owner for your Monument Square vacation rental?

What makes our Rentals by Owner 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 Monument Square Rentals by Owner

Where are the best neighborhoods to stay in Monument Square?

When exploring your options for a stay in Portland, Maine, selecting the right neighborhood to match your preferences is essential. The vibrant area around Monument Square offers a central location with easy access to the city's charming streets and local amenities. By choosing a rental in this neighborhood, you can enjoy the lively atmosphere and convenient proximity to downtown attractions. Whether you're seeking a cozy retreat or a spacious home, Rent By Owner provides reliable vacation rentals in the heart of Portland, Maine, ensuring your visit is comfortable and memorable.

Downtown Portland

Stay in the heart of the city where you can enjoy convenient access to local shops, dining, and cultural attractions within the vibrant downtown area.

View 275+ Rentals in Downtown Portland

Old Port

This historic district offers charming cobblestone streets and waterfront views, making it an ideal location for exploring Portland’s maritime heritage.

View 174+ Rentals in Old Port

Pine Point

Located along the coast, Pine Point provides a serene setting for those seeking beachside relaxation close to Portland’s lively scene.

View 77+ Rentals in Pine Point

Parkside

Nestled near green spaces and the bustling city center, Parkside offers a peaceful retreat with easy access to Portland’s urban amenities.

View 57+ Rentals in Parkside

West End

Known for its historic architecture and scenic views, the West End is perfect for travelers looking to experience Portland’s charm and elegance.

View 75+ Rentals in West End

West Bayside

This neighborhood features a mix of modern developments and local businesses, providing a dynamic atmosphere close to Portland’s core.

View 589+ Rentals in West Bayside

East Bayside

Easily accessible from the city center, East Bayside boasts a diverse community and vibrant local culture, ideal for authentic Portland experiences.

View 36+ Rentals in East Bayside

East End

Perched along the waterfront, the East End offers stunning vistas and a trendy vibe, making it a desirable choice for memorable stays.

View 89+ Rentals in East End

Best Times to Visit Monument Square

When should you plan your Rentals by Owner stay?

Determining the optimal time to visit here can help you enjoy the area's vibrant atmosphere and make the most of your rental experience, whether you're seeking lively local events or a quieter retreat in Portland's charming surroundings.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, the area comes alive with outdoor activities and events, making it an ideal time for travelers seeking lively atmospheres and vibrant cityscapes in Portland's historic district.

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

Autumn offers colorful foliage and a welcoming ambiance that draws visitors to enjoy the region's scenic beauty and local festivals, enhancing your stay in this charming destination.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The colder months bring fewer crowds, providing a quiet and cozy experience in this area, perfect for exploring indoors or enjoying peaceful walks without the busy tourist season.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

As the city awakens from winter, you can enjoy less crowded streets and mild weather, creating a perfect opportunity for relaxed sightseeing and discovering the local charm.

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

Weekly Weather Forecast for Monument Square

How to Book Your Monument Square 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 Monument Square

More Top-Rated Rentals by Owner in Monument Square 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 a private outdoor seating area or patio to relax after exploring the city.
  • Take advantage of communal outdoor spaces such as gardens or courtyards available at some rentals.
  • Find properties with direct access to nearby parks or green spaces for outdoor recreation.
  • Look for rentals that offer outdoor grilling or barbecue facilities to enhance your culinary experience.
  • Experience scenic views from balconies or terraces overlooking the vibrant neighborhood.
  • Utilize on-site bicycle storage or rental options for exploring the area's historic streets and waterfront.
  • Enjoy easy access to outdoor activities like walking trails or waterfront strolls, just steps from your accommodation.

Top Attractions Around Monument Square

What attractions are nearby?

Nearby, you can explore a variety of cultural events, enjoy local dining options, or stroll through the vibrant streets that capture the true essence of this destination’s charm and character.

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Family Activities

  • Visit the Portland Freedom Trail: Explore this family-friendly outdoor history trail that highlights significant sites connected to the region’s role in abolition and civil rights.
  • Attend a Local Event at Monument Square Park: Enjoy seasonal festivals, live performances, or community markets right in the heart of the area that caters to visitors of all ages.
  • Explore the Portland Museum of Art: Engage your family with inspiring art exhibits and interactive programs housed within easy reach from here.
  • Take a Walking Tour of Historic Downtown: Discover charming streets, unique shops, and iconic landmarks while strolling through this vibrant part of the city.
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Adult Activities

  • Historical Walking Tour: Explore the rich history of this iconic area with guided or self-guided walks that reveal its storied past and vibrant architecture.
  • Local Art Galleries: Visit nearby art galleries to immerse yourself in Maine's creative scene, showcasing works by regional artists inspired by the region's maritime heritage.
  • Craft Beer Tastings: Savor the flavors at local breweries and enjoy craft beer tastings that highlight the area's blossoming brewing culture.
  • Farmers' Market Visits: Shop for fresh, locally sourced products at the regional farmers’ market, perfect for experiencing the region’s culinary traditions firsthand.

Monument Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local eateries and cafes: Take advantage of the area's vibrant food scene by sampling fresh, regional dishes at nearby establishments to enrich your stay.
  • Enjoy outdoor activities around the square: Make the most of the scenic surroundings by walking or biking through nearby parks and historic sites in this charming destination.
  • Visit during special events: Check the local calendar for seasonal festivals or markets that showcase the region's unique culture and community spirit.
  • Utilize convenient transportation options: Maximize your time by choosing walkable accommodations and exploring the area with public transit or bike rentals available nearby.

Transportation Options

  • Walking: You can enjoy the charming streets of this historic area by walking, which provides an intimate experience of the local shops and cafes near Monument Square.
  • Public Transit: The region offers reliable bus services connecting you to various parts of the city, making it easy to explore without hassle.
  • Bike Rentals: Biking is a popular option here, with bike rental stations available for effortless navigation around the lively neighborhood.
  • Taxi and Rideshare Services: Convenient taxi and rideshare options are readily available, offering quick transportation to your preferred destinations in the region.

Local Customs Options

  • Greetings and Personal Space: In the area surrounding Monument Square, it’s customary to greet locals with a friendly nod or smile as a sign of respect and openness.
  • Respect for Historic Sites: When visiting historic landmarks near here, ensure you observe signage and stay on designated paths to preserve the region’s cultural heritage.
  • Food and Dining Etiquette: Tipping generously at local eateries reflects appreciation for the region’s service industry, which is integral to your authentic experience.
  • Community Events: Participating in seasonal festivals and markets demonstrates respect for local traditions and enhances your connection with the area's vibrant community.

Frequently Asked Questions About Monument Square Rentals by Owner

1. What are the top vacation rentals in Monument Square?

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

2. How many Rentbyowner vacation rentals are available in Monument Square?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 536 in the Monument Square 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 Monument Square. 

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

The cancellation policy varies by listing; you should review the specific rental's terms on the booking page or contact the owner directly to understand the refund and cancellation conditions.

4. How do I communicate with the property owner before booking?

You can reach out to the owner through the messaging feature provided on the Rent By Owner platform to ask questions about the rental, amenities, or any special requests.

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

Additional fees such as cleaning fees, service charges, or security deposits are detailed in the listing. Always read the full description and terms before confirming your reservation.

6. What amenities are typically included in rentals near the local attractions?

Listings often include essential amenities like Wi-Fi, kitchen facilities, and linens; check each property’s detailed description to ensure it meets your needs.

7. Is there a minimum stay requirement for booking in this destination?

Minimum stay requirements vary by property; you should verify these details on the listing page or inquire with the owner to confirm your travel plans align.

More Rentals You May Like Near Monument Square

10.0 (1 Review)
House
Pearl of Portland
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
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More Top-Rated Rentals by Owner in Monument Square Area