Best Vacation Homes in Portland
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Parking
- TV
- Balcony/Terrace
- Parking
- View
- Ocean View
- Air Conditioner
- Parking
- Pool
- Parking
- Pet Friendly
- Security/Safety
Portland Luxury Rentals
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Parking
- View
- Wheelchair Accessible
- Air Conditioner
- Parking
- TV
Portland Pet Friendly Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Portland Large Vacation Homes
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pool
- View
- Air Conditioner
- Parking
- TV
Why Choose Rent By Owner for your Portland Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Portland Vacation Rentals
Where are the best neighborhoods to stay in Portland?
Discover the diverse neighborhoods of Portland, Maine, that offer unique experiences for your stay. Whether you prefer the charming streets lined with historic architecture or vibrant districts buzzing with local cafes and shops, each area provides a distinct atmosphere to enhance your visit. Choosing the right neighborhood ensures you’re close to the city's best attractions while enjoying the comfort and convenience of well-appointed vacation rentals. With a range of options across Portland’s neighborhoods, you can easily find a location that suits your style and needs for a memorable trip to this beautiful coastal city.
Downtown Portland
Staying in Downtown Portland offers convenient access to the city's vibrant shops, restaurants, and cultural attractions, making it an ideal base for exploring this dynamic area. Here, you'll enjoy the blend of urban energy and historic charm that defines the heart of the region.
View 139+ Rentals in Downtown PortlandOld Port
This historic district is perfect if you seek charming waterfront views and a lively atmosphere filled with boutique shops and eateries. Its scenic streets and maritime heritage make it a captivating place to stay within the region.
View 57+ Rentals in Old PortPine Point
Offering picturesque coastal views, Pine Point provides a relaxing retreat near the sands and surf, ideal for those looking to unwind by the water. Its peaceful ambiance makes it a sought-after destination for beach lovers.
View 60+ Rentals in Pine PointCamp Ellis
Located along the shoreline, Camp Ellis is renowned for its quiet beaches and natural beauty, creating a tranquil setting for your stay. It’s the perfect spot to enjoy coastal serenity away from busier areas.
View 37+ Rentals in Camp EllisParkside
Situated close to Portland’s central attractions, Parkside offers a balance of accessibility and local charm, ideal for travelers wanting to explore the city while staying in a friendly neighborhood. It’s an excellent choice for experiencing authentic regional life.
View 45+ Rentals in ParksideWest End
Known for its historic architecture and tree-lined streets, the West End provides an elegant and tranquil environment within easy reach of downtown. It’s perfect for those seeking a refined atmosphere during their visit.
View 60+ Rentals in West EndFortunes Rocks
This beachfront community boasts stunning ocean vistas and a peaceful setting, making it an ideal location for seaside relaxation. Its natural beauty attracts visitors looking for a serene coastal escape.
View 228+ Rentals in Fortunes RocksWest Bayside
West Bayside is a lively neighborhood known for its eclectic character, vibrant food scene, and local arts. Staying here provides a unique opportunity to immerse yourself in the region’s creative spirit.
View 589+ Rentals in West BaysideBest Times to Visit Portland
When should you plan your Vacation Rentals stay?
Choosing the best time to visit here can enhance your experience, as each season offers unique opportunities to enjoy the area's natural beauty and local charm.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences warm weather that attracts visitors looking for outdoor activities and scenic coastal views. This is a popular time to book vacation rentals near the area's beaches and parks.
Fall (September to November)
The fall season showcases vibrant foliage and mild temperatures, making it an ideal time to explore outdoor attractions and enjoy seasonal festivals in this destination. Vacation rentals tend to fill up quickly during this picturesque period.
Off-Season Highlights
Winter (December to February)
In winter, the region features colder weather with fewer tourists, offering a quieter and more relaxed atmosphere for your stay. It’s a good time to find cozy vacation rentals at lower rates.
Spring (March to May)
Spring brings milder weather and blooming landscapes, yet it remains less crowded than peak seasons. This makes it a suitable period to enjoy the area's natural beauty while securing affordable vacation rentals.
Weekly Weather Forecast for Portland
How to Book Your Portland Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Portland
Common Vacation Rentals Amenities
What amenities can you expect?
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 a day exploring the region.
- Take advantage of a spacious backyard ideal for outdoor dining, barbecues, or family gatherings.
- Benefit from access to scenic walking trails or gardens nearby, offering a peaceful escape in this destination.
- Make use of outdoor furniture and loungers to unwind while soaking up the natural beauty of the area.
- Utilize on-site parking facilities with easy access to local attractions in the region.
- Experience outdoor recreational amenities such as a fire pit for cozy evenings outdoors.
- Access well-maintained lawns or landscaped areas that enhance your overall stay in this destination.
Top Attractions Around Portland
What attractions are nearby?
In this charming destination, you can explore a variety of outdoor activities, cultural attractions, and local dining experiences just moments from your vacation rentals, ensuring an enjoyable stay immersed in the best of what the region has to offer.
Family Activities
- Portland Head Light: Explore this historic lighthouse and enjoy picturesque views that make for memorable family photos along the rugged Maine coast.
- Children’s Museum & Theatre of Maine: Engage your family in interactive exhibits and live performances designed to inspire creativity and learning for kids of all ages.
- Eastern Promenade Park: Relax and play in this scenic waterfront park featuring walking trails, playgrounds, and stunning views of Casco Bay—perfect for family picnics and outdoor fun.
- Casco Bay Islands: Take a ferry to nearby islands where you can explore beaches, hiking trails, and charming villages that appeal to adventurers and relaxation seekers alike.
Adult Activities
- Explore the Portland Museum of Art: Immerse yourself in impressive collections that highlight regional and international art, perfect for a cultural day in the city.
- Stroll along the Old Port Waterfront: Enjoy scenic views, boutique shopping, and local eateries in this vibrant district known for its historic charm and lively atmosphere.
- Visit the Eastern Promenade: Take in breathtaking harbor vistas while walking or cycling along this scenic park, ideal for relaxing outdoors near the region's coastal beauty.
- Indulge in Culinary Experiences: Savor fresh seafood and innovative cuisine at renowned restaurants that showcase the area's rich maritime traditions and creative chefs.
Other Places to Stay in Portland, ME
Portland Travel Tips
How Can You Make the Most of Your Stay?
- Explore the Waterfront: Take advantage of the area's scenic harbor and waterfront parks to enjoy leisure walks and boat watching, enriching your stay in this coastal destination.
- Sample Local Cuisine: Dine at local eateries and seafood restaurants to experience authentic regional flavors that highlight the region’s maritime heritage.
- Visit Cultural Spots: Immerse yourself in the area's artistic and historical sites to gain a deeper understanding of its vibrant community and traditions.
- Plan for Seasonal Events: Check the calendar for festivals and events happening during your visit to make memorable experiences in this charming destination.
Transportation Options
- Portland Transportation Services: You can explore the area conveniently using local transportation options tailored for visitors seeking comfort and reliability.
- Public Transit - Metro Breez Bus: This eco-friendly bus service provides easy access to key attractions and neighborhoods throughout Portland, Maine.
- Rental Cars: Renting a vehicle gives you the flexibility to discover the region at your own pace, especially if you're planning day trips outside the city.
- Bike Rentals and Pedestrian Paths: Navigating here on bike or foot is both enjoyable and practical, with scenic routes that highlight the area's natural beauty.
Local Customs Options
- Seafood Dining Etiquette: Embrace the region's maritime heritage by enjoying fresh seafood at local eateries, a cherished custom that highlights Portland’s coastal charm.
- Lobster Shack Visits: Visiting a lobster shack is a popular local tradition, allowing you to experience authentic Maine cuisine directly from the source here in the area.
- Fishermen’s Festivals: Participating in seasonal festivals celebrates the area's rich fishing history and provides an opportunity to engage with the community’s maritime customs.
- Preservation of Historic Sites: Respect for the region’s historic architecture and landmarks reflects the community’s pride in maintaining its cultural heritage during your stay.
Portland Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Portland?
There are a lot of options in Portland. If you plan on staying in the Portland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Portland:
- Penthouse Two Master Waterfront Suite with Rooftop
- Old Port Penthouse Suite - Amazing Harbor Views
- Downtown Penthouse Suite - Stunning Harbor Views
- Chic One Bedroom Apartment In Portland's Arts District
- Waterfront Two Master Suite Penthouse with Rooftop
- Stunning Waterfront Condo with deck, Walk to Shops and Restaurants
- Fully Furnished Executive/Garden Apartment In Falmouth, Maine
- Luxury 5 Bed 4 1/2 Bath - Family Friendly, walk to town, close to beaches
- The James Place Inn B&B
- Glorious getaway on Portland's Eastern Promenade.
2. How many vacation rentals have private pools in Portland?
There are 101 vacation rentals with private pools near Portland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Portland are best for families?
If you are looking for a family-friendly vacation home in Portland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Portland:
4. How many Rentbyowner vacation rentals are available in Portland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 4018 in the Portland 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 Portland.
5. What is the cancellation policy for vacation rentals in Portland, Maine?
6. How do I confirm my reservation and what are the payment options?
7. Are linens and utilities included with the stay at rental properties in this area?
8. What amenities should I expect when booking a vacation rental here?
9. Is there a minimum stay requirement for booking a rental in this destination?
Portland Top Rated Vacation Rentals
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
