Portland vacation rentals

We found 654 vacation rentals — enter your dates for availability

Discover a selection of 16 homes, 10 apartments, and other vacation rentals in Portland that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you expect for your stay, which might include WiFi and a hot tub. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
  • Peace of mind
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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find out more about Portland

Find out more about Portland

Why visit Portland

  1. Scenic Coastal Paths: Explore breathtaking coastal paths that showcase Portland's stunning natural beauty.
  2. Historic Castles: Visit the area's historic castles, offering a glimpse into the region's rich cultural heritage.
  3. Beautiful Beaches: Enjoy relaxing days on picturesque beaches, perfect for sunbathing and beach activities.
  4. Vibrant Harbour: Experience the lively harbour, ideal for local dining and water-based adventures.
  5. Diverse Accommodation: Choose from charming cottages to modern beach houses for a perfect home base.

Popular types of accommodation in Portland

Planning a getaway to Portland? Discover the perfect home away from home with our selection of vacation rentals! From charming cottages and houses to modern apartments, Portland offers a variety of accommodation options to suit every traveller's needs. If you're looking for beachfront rentals, explore our stunning beach houses and beachfront vacation rentals that provide easy access to the beautiful coast. Start your Portland adventure with the ideal place to stay!

  • Cottages: These charming, quaint accommodations are the top choice for visitors seeking a cozy and inviting experience in Portland.
  • Houses: Ideal for families or groups, these spacious homes offer a comfortable and personal atmosphere for your stay.
  • Apartments: Perfect for solo travellers or couples, these self-contained units provide convenience and a taste of local living.
  • Cabins: For those wanting a rustic escape, cabins in the area offer a unique blend of comfort and nature.
  • Caravan Parks: A fun and budget-friendly option, caravan parks provide a lively atmosphere for adventurous travellers.**

Top attractions in Portland

Portland, England, is perfect for outdoor enthusiasts seeking scenic adventures. With its stunning beaches, historic castles, and vibrant harbour, this charming destination offers a rich cultural experience. You can explore coastal paths, enjoy beachfront rentals, or indulge in a surf vacation. Whether you’re planning a beach trip or a relaxing beach vacation, Portland has something for every traveller looking to embrace nature and history.

  1. Weymouth Beach: A picturesque beach boasting golden sands and vibrant beach vibes, perfect for sunbathing and leisurely strolls. It's located 8.0km from Portland, offering a quintessential British seaside experience.
  2. Weymouth Harbour: This charming harbour, situated 6.4km away from Portland, combines scenic views with a lively atmosphere, making it ideal for enjoying the waterfront and local eateries.
  3. Portland Bill Lighthouse: A historic lighthouse steeped in culture, located within Portland, it offers stunning coastal views and a glimpse into maritime history, making it a must-visit.

Things to do recommended for couples

Planning a romantic getaway in Portland? Enjoy thrilling water sports at the Weymouth and Portland National Sailing Academy, challenge each other at the Pirate Adventure Mini Golf, and savour a delightful meal at Mangerton Mill, perfect for intimate dining amidst a charming atmosphere.

Things to do recommended for families

Families visiting Portland, England can relax at Lodmoor Country Park, just 9.7km away, or enjoy a day at Greenhill Beach, located 8.0km from Portland. For sports enthusiasts, The Avenue Stadium, 17.7km away, offers an exciting atmosphere for all ages.

Things to do recommended for groups

Experience the vibrant culture at Weymouth Pavilion, enjoy scenic hikes on the South West Coast Path, or challenge your group to a round of golf at Bridport and West Dorset Golf Club. Each activity offers unique adventures and memorable moments together!

What do I need to keep in mind when booking a vacation in Portland

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Portland with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Portland with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many families, a vacation wouldn’t feel complete without their furry companion by their side. If you can relate to this, we invite you to explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right destination. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Additionally, think about including amenities such as a parking spot, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Portland

Portland, England, offers a delightful blend of outdoor adventures and historical charm. With its stunning beachfront homes and picturesque seaside spots, visitors can unwind while soaking up the friendly atmosphere. Explore the nearby coastal towns for family-friendly recreation and relaxing vibes, or enjoy the beautiful beaches that make this region a perfect vacation destination. Whether you're seeking scenic views or a taste of local history, Portland has something for everyone.

  • Weymouth: Located a mere 8.0km from Portland, Weymouth is a vibrant coastal city known for its stunning beaches and lively atmosphere. Visitors flock to Weymouth for outdoor adventures, including water sports and scenic walks along the shoreline. The city's renowned theatre and recreational areas provide entertainment for all ages. Don't miss the iconic Weymouth Beach, where you can relax on golden sands or explore the intriguing rock formations that line the coast, making it a perfect spot for family outings.
  • Dorchester: Situated 17.7km from Portland, Dorchester is a historic city rich in culture and charm. Surrounded by beautiful countryside, it offers a delightful blend of outdoor experiences and scenic beauty. Explore local recreational areas and campgrounds, perfect for nature enthusiasts. Key attractions include the nearby beaches and captivating rock formations, as well as access to the stunning Dorset National Park. Dorchester's quaint streets are lined with intriguing shops and eateries, offering a taste of local life.
  • Southwell: Nestled within the Portland area, Southwell is a picturesque village that offers a tranquil escape for those seeking outdoor adventures. With a strong focus on water sports and educational activities, it's an ideal spot for families and individuals alike. Visitors can enjoy the stunning beaches, visit historical monuments, and explore the famous lighthouse that stands as a beacon along the coast. The local country private club provides a welcoming atmosphere for those looking to unwind and socialize in a beautiful setting.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from July to September, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January44.6°F (7.0°C)Light RainMostly CloudyLowAverage
February44.4°F (6.9°C)Light RainMostly CloudyLowSlightly Low
March46.0°F (7.8°C)Light RainMostly CloudyAverageSlightly Low
April49.1°F (9.5°C)Light RainMostly SunnyAverageAverage
May53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
June58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
July62.2°F (16.8°C)Light RainMostly SunnyHighSlightly High
August62.4°F (16.9°C)Light RainMostly SunnyHighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyHighAverage
October56.5°F (13.6°C)Light RainMostly CloudyAverageAverage
November50.9°F (10.5°C)Light RainMostly CloudyLowSlightly Low
December47.3°F (8.5°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? It might be beneficial to remain flexible with your travel dates, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume your previous arrangements, or manage your travel plans with ease. Here, you'll find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The friendly city of Portland awaits you

Enjoy the history and other features of Portland. Travelers to this welcoming city praise the sailing, bars and windsurfing. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Portland

Are you hoping to find top things to see and do while you're in town? Venture out of your vacation home and experience everything that makes Portland a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • SEA LIFE Centre Weymouth (5.6 mi / 9 km)
  • Abbotsbury Swannery (10.6 mi / 17 km)
  • Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 km)
  • Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
  • The Blue Pool and Tea House (16.6 mi / 26.7 km)
  • Pirate Adventure Mini Golf (5.7 mi / 9.1 km)

Exploring the natural features in Portland

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Portland is a great place to get out in nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Durdle Door (8.7 mi / 14 km)
  • Portland Bill (2.1 mi / 3.3 km)
  • Chesil Beach (2.8 mi / 4.5 km)
  • Weymouth Harbour (4.5 mi / 7.2 km)
  • Weymouth Bay (4.5 mi / 7.2 km)
  • Weymouth Beach (4.6 mi / 7.4 km)

Traveling to and around Portland

The nearest airport is in Bournemouth (BOH-Bournemouth Intl.), located 30.9 mi (49.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Portland when booking a vacation rental?
If you’re thinking about a stop in Portland, Southwell is one of the more sought-after locations to spend a getaway. While you’re here, pay a visit to fantastic attractions like Portland Bill Lighthouse and Church Ope Cove.
What is the most popular type of vacation rental accommodation in Portland?
Based on our data, cottages are the most desirable type of property in Portland. But of course, everyone’s idea of an epic trip can differ. Vrbo has vacation homes of all shapes and sizes, and we’ll help you find the perfect fit.
How much does it cost to rent a vacation rental in Portland?
Length of stay, property type and time of year are some of the things that can affect the price of a vacation home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling luxury villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in Portland?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside stay. Put in your Portland travel dates to see all your options on Vrbo. Did someone just say “private pool”? Use our filters to choose the amenities and features you need.
Are there pet-friendly vacation rentals in Portland?
With 68 vacation rentals that welcome four-legged guests, your furry companion can join in the fun on your Portland vacation. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
Can I rent a house with a pool in Portland?
Add an extra layer of fun to your trip by booking your crew into one of the four houses with a private pool in Portland. Use our handy search filter to find the kind of property you want on Vrbo, and then spend leisurely days frolicking in a swimming pool that’s for your use only.
What are popular rental amenities in Portland?
A firepit, a fireplace and a swimming pool are the most popular rental amenities in Portland. Whether you’re planning to travel on your own, with your significant other or a group of family members, Vrbo can help you find a vacation rental that matches your tastes with a load of extras you’ll love.
Are there large group vacation rentals in Portland?
With 29 Portland vacation rentals that can sleep five or more people, you can bring a few extra friends or family members along. Whether you’re planning an informal get-together or a birthday party, we’ll help you find a comfortable space to match the occasion.
Are there vacation rentals in Portland that welcome kids?
Bring the entire family together for an adventure in Portland at one of our 68 family-friendly vacation homes. A lot of these stays offer conveniences that are ideal for trips with children, including full kitchens, extra bedrooms and patios. Just click on the “Properties good for families” filter and choose your favorite.
What are the top attractions for families in Portland?
Keeping the kids occupied during your Portland vacation is easy with these fabulous family-friendly attractions:

  • Weymouth Beach
  • Chesil Beach
  • SEA LIFE Centre Weymouth

Are there one-bedroom vacation rentals in Portland?
Yes, Portland has seven one-bedroom rentals on offer. Usually located in prime areas thanks to their compact size, a one-bedroom property is perfect if you’re traveling with your partner or a buddy. And with home comforts such as air conditioning and more privacy than a standard hotel, you’ll be able to chill out while exploring this amazing destination.
Can I find two-bedroom vacation rentals in Portland?
Gather your nearest and dearest and relax in total privacy and comfort in one of the 25 two-bedroom vacation properties Portland has to offer.
Are there vacation rentals with WiFi in Portland?
Take your pick of seven vacation rentals with WiFi in Portland. If you’d like to disconnect from the world on your vacation, but still want to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Portland?
The minimum required age is generally 16, 18 or 21. It can vary between properties on Vrbo, so look at the rules of your preferred Portland stay before booking your escape.
How long can I rent a vacation rental in Portland for?
The amount of time you can stay in a Portland vacation home for differs depending on the property. Just tap in your preferred travel dates to see available options that offer long-term stays. They come with all you require to make your extended break more comfortable like kitchens and laundries. Some properties might also offer discounted weekly or monthly prices, so you can stay even longer for less.

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