Discover Your Perfect Ladd's Circles & Squares Vacation Homes

Best Vacation Homes in Ladd's Circles & Squares

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10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.6 (201 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Accessibility
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10.0 (3 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

Why Choose Rent By Owner for your Ladd's Circles & Squares 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.

Best Times to Visit Ladd's Circles & Squares

When should you plan your Vacation Rentals stay?

Finding the ideal time to visit allows you to enjoy the local charm and vibrant atmosphere here, ensuring your stay in this destination aligns perfectly with your travel plans.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, this destination experiences warm weather and longer daylight hours, making it ideal for exploring outdoor attractions and enjoying pleasant evenings in the area.

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

The early fall season offers mild temperatures and vibrant foliage, perfect for sightseeing and relaxing in your vacation rentals while enjoying the region’s scenic beauty.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

Winter brings cooler temperatures, but this quieter time allows you to experience the region’s cozy atmosphere and less crowded vacation rentals.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
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Spring (March to May)

In early spring, the area begins to blossom with mild weather, providing a peaceful setting for those seeking a more relaxed visit before the busy summer season begins.

Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F

Weekly Weather Forecast for Ladd's Circles & Squares

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.

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 patio or deck perfect for relaxing after exploring the neighborhood
  • Benefit from access to well-maintained gardens or green spaces within walking distance
  • Take advantage of outdoor dining areas ideal for savoring local cuisine under the stars
  • Make use of parking facilities that accommodate your vehicle securely during your stay
  • Experience outdoor amenities like barbecue grills for cookouts with family and friends
  • Relax in shaded outdoor seating areas designed for enjoying the pleasant climate here
  • Utilize nearby walking or biking paths to explore the vibrant surroundings at your own pace
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Family Activities

  • Portland Children's Museum: Engage your family in interactive exhibits and hands-on activities that nurture creativity and curiosity in the area's family-friendly museum.
  • Oregon Museum of Science and Industry (OMSI): Explore engaging science exhibits, live demonstrations, and an impressive planetarium that captivates visitors of all ages here in the region.
  • Portland Japanese Garden: Experience tranquility and cultural enrichment as you stroll through this serene garden, offering a peaceful retreat for families seeking outdoor activities.
  • Forest Park Trails: Discover lush forest paths ideal for family hikes and nature walks, providing fresh air and scenic views close to the city.
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Adult Activities

  • Explore the Portland Art Museum: Immerse yourself in regional and contemporary art collections that showcase the vibrant culture of this destination.
  • Discover local breweries and pubs: Enjoy tasting sessions at some of the area's renowned breweries, perfect for relaxing evenings in Portland's craft beer scene.
  • Stroll through nearby parks and green spaces: Experience outdoor tranquility at popular spots like Laurelhurst Park or Mt. Tabor Park, offering scenic views and peaceful retreats.
  • Visit the Portland Saturday Market: Browse handcrafted goods and local fare at this bustling market, ideal for a leisurely day in the region.

Ladd's Circles & Squares Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Neighborhood: Take time to walk around and discover the unique local shops and eateries that define this vibrant area.
  • Maximize Your Outdoor Experience: Utilize nearby parks and outdoor spaces to enjoy the region's natural beauty and relax during your stay.
  • Plan Your Transportation: Consider bike rentals or public transit options available locally to navigate easily and immerse yourself in the area's surroundings.
  • Engage with the Community: Attend local events or markets to connect with residents and gain authentic insights into the destination.

Transportation Options

  • Portland Streetcar: This convenient urban transit option offers easy access to the area's key attractions and neighborhoods within the region.
  • Public Bus Service: The extensive bus network connects you seamlessly around here, making local travel straightforward and budget-friendly.
  • Bike Rentals: With dedicated bike lanes and scenic routes nearby, cycling provides a flexible way to explore this destination at your own pace.
  • Rideshare Services: Popular ride-hailing apps operate reliably here, offering quick transportation for trips within the neighborhood and beyond.

Local Customs Options

  • Community Gatherings: Residents often participate in neighborhood potlucks and local events that foster a strong sense of community here.
  • Respect for Green Spaces: There is a local custom of maintaining cleanliness and respecting the nearby parks, reflecting the area's commitment to sustainability.
  • Local Art Appreciation: Supporting and displaying public art pieces is a cherished tradition, showcasing the area's vibrant creative spirit.
  • Eco-Friendly Practices: Many locals embrace environmentally conscious habits like recycling and biking, aligning with the region’s eco-awareness ethos.

Frequently Asked Questions About Ladd's Circles & Squares?

2. How many Rentbyowner vacation rentals are available in Ladd's Circles & Squares?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1698 in the Ladd's Circles & Squares 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 Ladd's Circles & Squares. 

3. What is the cancellation policy for vacation rentals in Ladd's Circles & Squares?

Cancellation policies vary by listing, so it’s important to review the specific details on each property’s page before booking. Contact the host directly if you have questions about potential refunds or flexible cancellation options.

4. Are there any house rules or restrictions I should be aware of when booking a vacation rental here?

Yes, each property has its own set of house rules which are outlined in the listing. Be sure to read these carefully to ensure your stay complies with the host’s requirements, including check-in procedures, pet policies, and noise regulations.

5. How do I find the most suitable vacation rental in this area for my travel dates?

Use the search filters available on the booking platform to specify your preferred dates, amenities, and property types. Reading guest reviews and viewing multiple listings can also help you find the best fit for your needs.

6. What amenities are typically included in vacation rentals in Portland’s Ladd's Circles & Squares neighborhood?

Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and parking. Additional features like outdoor spaces, laundry, or additional guest accommodations are usually listed in the property description, so check each listing for specifics.

7. Who should I contact if I encounter issues during my stay or need further assistance with my reservation?

You should reach out directly to the property owner or the local support team through the contact details provided in your booking confirmation. They will assist you promptly to resolve any concerns or questions regarding your stay.

Best Vacation Homes in Ladd's Circles & Squares