Portland holiday lettings

We found 664 holiday rentals — enter your dates for availability

Select from 17 homes, 85 cottages and other holiday rentals in Portland to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.
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  • All the privacy of home

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  • More for less

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Why visit Portland

  • Stunning coastal views: Experience breathtaking scenery at Portland Bill and along the rugged coastline.
  • Historic attractions: Discover the rich heritage of Portland through its impressive castles and historical sites.
  • Outdoor activities: Enjoy a variety of pursuits such as walking, cycling, and relaxing on beautiful beaches.
  • Family-friendly parks: Unwind in lovely green spaces like Southwell Park, perfect for all ages.
  • Charming accommodation: Stay in delightful cottages or modern apartments that offer comfort and convenience.

Popular types of accommodation in Portland

If you're pondering where to stay in Portland, look no further. Our most sought-after accommodation options include charming cottages, private holiday homes, and modern apartments. Whether you're after cosy holiday lets or self-catering accommodation, we have a variety of Portland holiday rentals to suit your needs. Enjoy the perfect blend of comfort and convenience during your stay in this picturesque coastal destination.

  • Cottages: The most sought-after accommodation type in Portland, offering charming and cosy stays, perfect for a relaxing getaway.
  • Houses: A popular choice for those seeking more space and privacy, ideal for families or groups travelling together.
  • Apartments: A convenient option for couples or solo travellers, providing a home-like atmosphere in the heart of the city.
  • Cabins: Quaint retreats that offer a rustic experience amidst nature, perfect for a peaceful escape.
  • Caravan Parks: A fun and affordable way to enjoy the outdoors, with facilities for those who love camping and caravanning.**

Top attractions in and around Portland

Portland offers a delightful blend of outdoor activities, stunning scenery, and adventurous pursuits, making it an ideal destination for your holiday. Visitors can explore beautiful beaches, historic castles, and bustling harbours, all while enjoying the rich culture and splendid natural experiences the area has to offer. Whether you're travelling solo, with family, or in a group, Portland has something to captivate every traveller.

  • Weymouth Beach: A stunning stretch of golden sands, perfect for sunbathing and swimming. Enjoy beach vibes with family-friendly facilities and a lively atmosphere, just 3.1km from Portland.
  • Weymouth Harbour: A picturesque harbour offering beautiful scenery and a vibrant maritime atmosphere. Delight in fresh seafood and charming shops, located only 2.5km from Portland.
  • Portland Bill Lighthouse: A historic lighthouse with a rich maritime heritage, providing a glimpse into local culture. Explore the surrounding area and enjoy breathtaking coastal views within Portland.

Things to do recommended for couples

For a romantic getaway in Portland, consider sailing at the Weymouth and Portland National Sailing Academy for an adventurous day on the water. Alternatively, enjoy a round of mini golf at Pirate Adventure Mini Golf, or savour a meal at the charming Mangerton Mill, perfect for couples.

Things to do recommended for families

During your family vacation in Portland, England, visit Lodmoor Country Park for relaxation, enjoy the sandy shores of Greenhill Beach, and catch an exciting match at The Avenue Stadium. Each location offers a unique experience, perfect for creating lasting memories with your loved ones.

Things to do recommended for groups

Groups visiting Portland can enjoy a performance at the Weymouth Pavilion for a touch of culture, hike the scenic South West Coast Path Section 49 for adventure, or challenge each other at the Bridport and West Dorset Golf Club for a fun day outdoors.

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

If you're travelling with a group, family, furry friends, or seeking extended stays, be sure to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Portland with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for these options and more on Vrbo.
  • Traveling to Portland with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with ensuring that suitable amenities, like a private swimming pool, are available. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Portland: If you're searching for holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include additional preferences such as a parking space, a well-equipped kitchen, or a private swimming pool in your search.

Where to stay near Portland

Portland, nestled in Dorset, offers an enchanting blend of outdoor adventures and historical charm. Visitors can explore the stunning views of Portland Bill, unwind in the family-friendly atmosphere of Southwell Park, or embark on a relaxing getaway in the picturesque surroundings. With its friendly locals and opportunities for luxury experiences, Portland invites you to discover its unique vibe while enjoying a delightful holiday in this captivating region.

  • Weymouth: Located a mere 3.1km from Portland, Weymouth is a charming seaside town famed for its stunning beach and scenic views. This vibrant destination is ideal for outdoor enthusiasts looking for adventure and relaxation alike. Visitors can enjoy a range of activities from exploring the local theatre to unwinding in recreational areas. The striking beach and unique rock formations provide perfect spots for family outings and photography, making Weymouth a delightful stop on your journey.
  • South Coast: Situated 3.7km from Portland, the South Coast is a picturesque stretch known for its breathtaking scenery and outdoor activities. This region offers great trail access for hiking enthusiasts and boasts a shopping mall centre for those looking to indulge in some retail therapy. The nearby national parks and beautiful beaches provide a perfect backdrop for exploring the natural beauty of the area. Whether you’re hiking through lush landscapes or enjoying a day by the shore, the South Coast has something for everyone.
  • Dorchester: A historic market town located 6.8km from Portland, Dorchester is rich in culture and surrounded by natural beauty. It’s a fantastic destination for those seeking outdoor adventures and scenic landscapes. The area offers numerous recreational venues and campgrounds, perfect for family activities or peaceful retreats. With its proximity to stunning beaches and national parks, Dorchester invites visitors to explore its unique geological features and engage with the great outdoors, providing a memorable experience.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new adventures, pick up from where you last left off, or manage your existing itineraries. You can easily locate properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The friendly city of Portland awaits you

Enjoy the history and other features of Portland. Travellers to this welcoming city praise the sailing, bars and windsurfing. With a holiday 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

Do you want to discover attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Portland a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • SEA LIFE Centre Weymouth (5.6 mi / 9 km)
  • Abbotsbury Swannery (10.6 mi / 17 km)
  • Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
  • Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 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 appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Portland. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around Portland

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

Frequently asked questions

What is the best area to stay in Portland when booking a holiday 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 holiday 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 holiday homes of all shapes and sizes, and we'll help you find the perfect fit.
How much does it cost to rent a holiday rental in Portland?
Length of stay, property type and time of year are some of the things that can affect the price of a holiday home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling luxury villas, all Vrbo holiday 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 holiday rentals in Portland?
With 68 holiday rentals that welcome four-legged guests, your furry companion can join in the fun on your Portland holiday. Use the filter tool to search our pet-friendly holiday 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 holiday rental that matches your tastes with a load of extras you'll love.
Are there large group holiday rentals in Portland?
With 29 Portland holiday 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 holiday rentals in Portland that welcome kids?
Bring the entire family together for an adventure in Portland at one of our 68 family-friendly holiday 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 favourite.
What are the top attractions for families in Portland?
Keeping the kids occupied during your Portland holiday is easy with these fabulous family-friendly attractions:

  • Weymouth Beach
  • Chesil Beach
  • SEA LIFE Centre Weymouth

Are there one-bedroom holiday 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 travelling 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 holiday rentals in Portland?
Gather your nearest and dearest and relax in total privacy and comfort in one of the 25 two-bedroom holiday properties Portland has to offer.
Are there holiday rentals with WiFi in Portland?
Take your pick of seven holiday rentals with WiFi in Portland. If you'd like to disconnect from the world on your holiday, 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 holiday 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 holiday rental in Portland for?
The amount of time you can stay in a Portland holiday 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.