Discover Your Perfect Monument Square Vacation Homes

Best Vacation Homes in Monument Square

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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 Monument Square 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 Monument Square Vacation Rentals

Where are the best neighborhoods to stay in Monument Square?

When planning your stay in Portland, Maine, exploring the neighborhoods around Monument Square is a fantastic choice. This central area offers convenient access to the city's vibrant downtown atmosphere and charming local streets, making it ideal for discovering authentic Portland experiences. Whether you're seeking lively city energy or relaxing moments, choosing a vacation rental near Monument Square allows you to immerse yourself in the heart of Portland’s unique character. With a variety of dependable lodging options, you can enjoy a seamless booking process and a comfortable base for your Maine adventure.

Downtown Portland

This area offers a vibrant mix of cultural attractions and lively street scenes, making it an ideal spot for exploring the city's urban charm. Staying nearby provides easy access to shops, dining, and entertainment within the region.

View 275+ Rentals in Downtown Portland

Old Port

Famous for its historic waterfront, this neighborhood features cobblestone streets and boutique shops perfect for a leisurely experience. Here, you can enjoy the authentic maritime atmosphere while being close to the best local eateries.

View 174+ Rentals in Old Port

Pine Point

Known for its scenic beachfront and relaxed vibe, this destination is perfect for those seeking tranquility by the ocean. Opting for accommodations in this part of the region ensures a peaceful retreat with stunning coastal views.

View 77+ Rentals in Pine Point

Parkside

This neighborhood combines green spaces with convenient city access, offering a balanced environment for outdoor activities and urban exploration. It’s a great choice for travelers who want to stay close to nature while still enjoying city amenities.

View 57+ Rentals in Parkside

West End

Characterized by historic architecture and tree-lined streets, this area provides an elegant setting for those looking to enjoy Portland’s refined side. Staying here gives you quick access to cultural sites and charming neighborhoods.

View 75+ Rentals in West End

West Bayside

With its eclectic mix of shops, cafes, and galleries, this part of town offers a lively and creative atmosphere. Booking here places you near vibrant local businesses and arts scenes central to the area's character.

View 589+ Rentals in West Bayside

East Bayside

Renowned for its industrial roots and modern revitalization, this community blends innovation with tradition. Staying in this part allows for easy exploration of both emerging businesses and historic districts.

View 36+ Rentals in East Bayside

East End

Offering stunning waterfront views and a trendy ambiance, the East End is perfect for visitors seeking scenic beauty and upscale dining options. Accommodations here provide a luxurious base for discovering Portland’s coastal elegance.

View 89+ Rentals in East End

Best Times to Visit Monument Square

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can enhance your experience here, allowing you to enjoy the local ambiance and seasonal offerings at their best in this charming destination.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm weather and lively local events, making it an ideal time for exploring the region’s vibrant atmosphere.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
autumn
Fall (September to October)

Autumn offers cooler temperatures and stunning foliage, creating a picturesque setting that enhances your experience of this destination in Maine.

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

Off-Season Highlights

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Spring (April to May)

Early spring sees fewer visitors, with mild temperatures that are perfect for enjoying the quiet charm of the area before the busy summer season begins.

Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F
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Winter (December to February)

During winter, the region transforms into a snowy retreat, providing a peaceful environment and cozy accommodations for those seeking a quiet escape.

Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F

Weekly Weather Forecast for Monument Square

How to Book Your Monument Square 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 Monument Square

More Top-Rated Vacation Rentals in Monument Square 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 outdoor seating areas perfect for relaxing after exploring the historic streets of this vibrant destination.
  • Take advantage of private or shared patios that offer scenic views of the surrounding cityscape and the bustling area.
  • Make use of communal gardens where you can unwind amidst greenery and native flora typical of this region.
  • Benefit from easy access to nearby parks and green spaces ideal for outdoor activities and picnics.
  • Utilize outdoor grilling stations if available, allowing you to enjoy local flavors in a friendly outdoor setting.
  • Relax on balconies or terraces overlooking the lively streets and historic architecture of this popular destination.
  • Discover outdoor recreational amenities such as bike racks or storage, facilitating your explorations around here.

Top Attractions Around Monument Square

What attractions are nearby?

While staying here, you can enjoy a variety of nearby activities, including exploring charming local shops, dining at acclaimed restaurants, and experiencing vibrant cultural events that make this destination a lively hub in the region.

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Family Activities

  • Visit the Portland Museum of Art: Engage with inspiring art collections that showcase the region’s rich cultural heritage, perfect for family outings in this historic district.
  • Stroll through the lively Farmers’ Market: Experience local flavors and fresh produce while enjoying a vibrant community atmosphere right in the heart of the area.
  • Explore the historic streets on a walking tour: Discover the charming architecture and stories behind this destination's notable landmarks with an informative guided or self-guided walk.
  • Relax at Heritage Plaza Park: Enjoy open green spaces where children can play and families can unwind amidst scenic views and local street performances.
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Adult Activities

  • Visit the Portland Museum of Art: Immerse yourself in diverse works of art and explore the region’s rich cultural heritage right in the heart of the city.
  • Enjoy an outdoor concert at the Merrill Amphitheater: Experience live music performances outdoors during warmer months, adding a vibrant touch to your stay here.
  • Explore local cafes and breweries: Savor locally brewed beers and artisanal coffee at the area’s popular spots, perfect for relaxing after a day of sightseeing.
  • Take a historic walking tour: Discover the area's history and architecture on guided or self-guided tours that showcase Portland's unique charm and stories.

Monument Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Local Dining Scene: Take advantage of the area’s renowned eateries to enjoy authentic regional flavors during your stay.
  • Visit During Off-Peak Hours: To experience a more relaxed atmosphere, plan visits to popular spots outside of peak times when the area tends to be busiest.
  • Use Public Transportation or Walk: Maximize your time and immerse yourself in the local vibe by choosing walking or public transit options around this destination.
  • Book Accommodation in Prime Locations: Selecting vacation rentals near key attractions ensures convenient access to the best experiences in the region.

Transportation Options

  • Portland Transportation System: The city's public transit network offers convenient bus routes that connect Monument Square to all major parts of this vibrant region.
  • Walking and Biking: Exploring the area on foot or by bike provides an immersive experience of Portland's charming streets and local attractions.
  • Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing options like Uber and Lyft are readily available for quick, comfortable rides around the bustling city center.
  • Rental Cars: Renting a car gives you the flexibility to discover scenic drives and nearby coastal destinations at your own pace from here.

Local Customs Options

  • Salutation of the Flag: During public events in Monument Square, it is customary to observe a respectful salute or national anthem, reflecting the area's appreciation for its local traditions.
  • Local Art Displays: You’ll often find artists showcasing their work around here; supporting local art during your visit enriches your experience of the region’s creative spirit.
  • Seasonal Festivals: Participating in seasonal festivals and community gatherings offers insight into the area's cultural heritage and local customs.
  • Respect for Historic Preservation: Respect for the historic architecture and public spaces is valued here, emphasizing the community’s commitment to maintaining its historic charm.

Frequently Asked Questions About Monument Square?

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 699 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 vacation rentals near Monument Square in Portland, Maine?

Cancellation policies vary by owner and property. To understand the specific terms, please review the listing details or contact the host directly for your selected accommodation in this area.

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

Additional fees such as cleaning or service charges are typically listed on the property page. It's recommended to read the full fee breakdown in the listing or reach out to the owner for clarification before completing your reservation.

5. How do I secure my booking for a vacation rental close to Portland’s historic district?

Secure your reservation by following the booking process outlined in the listing. Most properties require payment at the time of booking, and confirmation will be sent once your reservation is complete. Contact the host if you have specific questions about your stay.

6. What amenities can I expect in vacation rentals around the downtown area?

Amenities vary by property but often include essentials like Wi-Fi, kitchens, and parking. To confirm what’s available, review each listing carefully or contact the owner directly to ensure your needs are met during your visit.

7. Is there a minimum stay requirement for booking vacation rentals in this part of Portland?

Minimum stay requirements depend on the individual property. Please check the property listing details or communicate with the owner to find out about any restrictions or special conditions for your desired travel dates.

Best Vacation Homes in Monument Square

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10.0 (1 Review)
Apartment
Monument Garden SWEET
  • Air Conditioner
  • Parking
  • Pet Friendly
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10.0 (1 Review)
House
Pearl of Portland
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
View Availability