Best Vacation Homes in Portland
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $225/Night
For 7 Nights CA $1,574
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- View
- Pet Friendly
CA $704/Night
For 7 Nights CA $4,924
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
CA $971/Night
For 7 Nights CA $6,796
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $327/Night
For 7 Nights CA $2,289
1076.39 ft²
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Parking
- Internet
CA $256/Night
For 7 Nights CA $1,790
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $229/Night
For 7 Nights CA $1,604
1561 ft²
7 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $554/Night
For 7 Nights CA $3,875
1130 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pool
CA $727/Night
For 7 Nights CA $5,090
Portland Luxury Rentals
20 Guests
9 Bedrooms
9 Bathrooms
Family Friendly
Other
- Private Pool
- Fireplace/Heating
- Pool
CA $5,961/Night
For 7 Nights CA $41,728
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $2,253/Night
For 7 Nights CA $15,771
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $1,887/Night
For 7 Nights CA $13,209
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $1,329/Night
For 7 Nights CA $9,299
CA $1,310/Night
For 7 Nights CA $9,170
Portland Pet Friendly Vacation Rentals
1001 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $363/Night
For 7 Nights CA $2,538
CA $1,202/Night
For 7 Nights CA $8,416
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $291/Night
For 7 Nights CA $2,038
462.85 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Parking
CA $207/Night
For 7 Nights CA $1,452
1130 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $634/Night
For 7 Nights CA $4,438
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $228/Night
For 7 Nights CA $1,598
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $166/Night
For 7 Nights CA $1,164
Portland Large Vacation Homes
1883 ft²
12 Guests
6 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $558/Night
For 7 Nights CA $3,906
1883.68 ft²
12 Guests
6 Bedrooms
2 Bathrooms
Group Friendly
House
- View
- Parking
- Internet
CA $999/Night
For 7 Nights CA $6,993
661.38 ft²
38 Guests
19 Bedrooms
17 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $185/Night
For 7 Nights CA $1,298
Why Choose Rent By Owner for your Portland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Portland
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures you enjoy the region’s unique charm and make the most of your stay, whether you're seeking pleasant weather or quieter periods in this destination.
Peak Season Highlights
June to August
During the summer months, you can enjoy longer daylight hours and generally warmer weather, making it ideal for exploring the area's scenic beauty and outdoor activities.
Average Temperature Daytime: 18°C to 22°C - Nighttime: 12°C to 15°C
December to February
The winter season offers a charming atmosphere with festive events and cozy evenings, perfect for experiencing local traditions and seasonal festivities.
Average Temperature Daytime: 7°C to 10°C - Nighttime: 2°C to 4°C
Off-Season Highlights
March to May
Springtime brings milder weather and blooming landscapes, providing a quieter period for visiting and enjoying the scenic surroundings without the crowds.
Average Temperature Daytime: 11°C to 16°C - Nighttime: 5°C to 9°C
September to November
Autumn offers a peaceful experience with colorful foliage and fewer visitors, making it an excellent time to explore this destination at your own pace.
Average Temperature Daytime: 13°C to 17°C - Nighttime: 8°C to 11°C
Weekly Weather Forecast for Portland
How to Book Your Portland 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 Portland
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 a private outdoor garden or patio space to relax and unwind amidst the natural surroundings.
- Take advantage of outdoor dining areas, perfect for savoring meals while enjoying the fresh air.
- Make the most of nearby walking trails or hiking paths that showcase the scenic beauty of the region.
- Benefit from accessible outdoor parking facilities for convenient arrival and departure.
- Experience outdoor seating arrangements that encourage socializing or quiet contemplation.
- Look for properties with outdoor recreational equipment such as bikes or kayaks for exploring the area's waterways and countryside.
- Seize opportunities for outdoor fire pits or barbecue grills, ideal for evening gatherings in this charming destination.
Top Attractions Around Portland
What attractions are nearby?
In this area, you can explore a variety of outdoor activities, visit scenic coastal spots, and enjoy local cultural attractions that showcase the beauty and history of Portland, England.
Family Activities
- Portland Bill Lighthouse Tour: Discover the iconic lighthouse with a family-friendly tour that offers breathtaking views of the coastline.
- The Portland Museum: Engage your family in the area's rich maritime history through interactive exhibits and inspiring displays.
- Portland Harbour Exploration: Spend quality time exploring the busy harbour, perfect for watching boats and enjoying scenic walks along the waterfront.
- Seal Watching Cruises: Embark on a family cruise around the region's waters to see playful seals and enjoy the natural beauty of this coastal destination.
Adult Activities
- Exploring Portland Castle: Discover the rich history and stunning coastal views at this historic fortress, offering a perfect blend of culture and scenery.
- Walking along Chesil Beach: Experience the tranquility and natural beauty of this famous pebble beach, ideal for relaxing strolls and scenic photography.
- Visit the Portland Museum and Heritage Centre: Immerse yourself in local history and maritime heritage through engaging exhibits conveniently located here.
- Enjoying outdoor activities at Portland Harbour: Engage in sailing, kayaking, or simply unwind by the waterfront while soaking up the region’s maritime atmosphere.
Other Places to Stay in Portland
Portland Harbour
Weymouth and Portland National Sailing Academy
Portland Beach
Portland Castle
Castletown
Royal Manor Theatre
The Olympic Rings Stone Sculpture
Verne High Angle Battery
Broadcroft Quarry Nature Reserve
Portland Museum
Rufus Castle
Southwell
Portland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Heritage: Take time to discover the area's rich history by visiting local landmarks and museums that provide insight into this destination's unique past.
- Enjoy Scenic Outdoor Activities: Make the most of the region's natural beauty with outdoor pursuits such as walking along coastal paths or exploring nearby countryside trails.
- Dine at Authentic local eateries: Savor regional cuisine by trying out well-loved restaurants and cafes that showcase the area's culinary traditions.
- Plan Your Transportation: Arrange reliable transportation options in advance to easily access key attractions and make your stay here more convenient and enjoyable.
Transportation Options
- Bus Services: Local bus routes provide convenient connections to explore the area and reach nearby attractions with ease.
- Railway Station: The nearby train station offers efficient travel options across the region, making day trips and commutes straightforward.
- Taxis and Private Hire Vehicles: Taxis are readily available for quick, reliable transportation around here, especially for those traveling with luggage or in groups.
- Car Rentals: Renting a car gives you the flexibility to explore the destination and its scenic surroundings at your own pace.
Local Customs Options
- Portland's Maritime Heritage: You can explore the area's deep connection to shipping and seafaring, which influences local customs and traditions.
- Traditional Seafood Dining: Enjoy the regional cuisine by indulging in fresh seafood, a staple customs of this coastal destination.
- Local Craftsmanship: Discover the region's artisan crafts, reflecting its maritime history through handmade goods and souvenirs.
- Community Festivals: Participate in community-led events that celebrate the area's maritime background, fostering a strong sense of local identity.
Frequently Asked Questions About Portland?
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:
- 1 bedroom accommodation in Portland
- Entire home hosted by Lisa
- Clifftops - Blue Lodge
- Chic and modern townhouse in beautiful Portland
- Modern one bedroom apartment
- SEA GEM, family friendly, with a garden in Castletown, Portland
- Sea Gem
- OLD HIGHER LIGHTHOUSE STOPES COTTAGE, with pool in Portland Bill
- 2 Bed in Portland oc-94598
- Bright & beautiful 4 bedroom house with sea views
2. How many vacation rentals have private pools in Portland?
There are 2 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 2026 is over 236 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 this area?
The cancellation policy varies depending on the individual property listing. You should review the specific terms outlined in the rental agreement or contact the property owner directly to understand the cancellation timeframe and any applicable fees.
6. Are there any specific check-in and check-out times I should be aware of when booking a vacation rental here?
Check-in and check-out times are set by each host, so it’s best to verify these details in the listing description or communicate with the owner beforehand to ensure a smooth arrival and departure experience.
7. What amenities are typically included in vacation rentals in this destination?
Amenities differ between properties, but common features include Wi-Fi, parking, kitchen facilities, and often, laundry services. For precise details, review the property listing or reach out to the owner directly.
8. How do I ensure my stay is secure and reliable when booking a vacation rental in this region?
Booking through a reputable platform ensures you have access to verified listings, secure payment options, and support in case of issues. Always read reviews, confirm the host’s credentials, and communicate through the platform’s messaging system.
9. Is there any additional information I should consider before confirming my reservation in this area?
It’s advisable to read the full property description, review the house rules, and contact the owner if you have specific questions about the location, accessibility, or nearby facilities to ensure your stay meets expectations.
Portland Top Rated Vacation Rentals
1130 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $605/Night
For 7 Nights CA $4,233
1130 ft²
4 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
CA $475/Night
For 7 Nights CA $3,325
1130.21 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Pool
- View
- Parking
CA $155/Night
For 7 Nights CA $1,082
1130.21 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Pool
- View
- Parking
CA $143/Night
For 7 Nights CA $1,002
CA $346/Night
For 7 Nights CA $2,424
107.64 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Private Pool
- Fireplace/Heating
- Pool
CA $300/Night
For 7 Nights CA $2,100
2389.59 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
CA $543/Night
For 7 Nights CA $3,800
CA $301/Night
For 7 Nights CA $2,111
