Portland holiday lettings

We found 709 holiday rentals — enter your dates for availability

Select from 16 homes, 81 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.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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 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:

  • 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)
  • Bowleaze Cove Beach (6.3 mi / 10.2 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?
When considering the best area to stay in Portland, England, for a holiday rental, you might want to explore the charming neighbourhoods that showcase the unique character of the island. One of the most appealing areas is the vicinity around the Portland Bill, which is renowned for its iconic lighthouse and stunning coastal views. This area offers an array of holiday rentals, ranging from quaint cottages to modern apartments, allowing visitors to enjoy the beauty of the rugged coastline.

Another excellent option is the village of Easton, where you'll find a delightful selection of properties, often featuring picturesque views and easy access to local amenities. Easton is not only a great base for exploring the island but is also close to attractions such as the Portland Museum, which provides fascinating insights into the island's history, and the beautiful Chesil Beach, superb for leisurely walks and enjoying the natural scenery.

In total, there are a variety of properties available throughout Portland, suiting different preferences and budgets, making it a wonderful destination for a relaxing getaway.
How much does it cost to rent a holiday home in Portland?
Prices for holiday rentals in Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Portland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Portland holiday house rentals?
You can find great discounts on house rentals in Portland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Portland?
For renting a beach house in Portland, England, the areas around the famous Chesil Beach are highly recommended. This stunning stretch of coastline offers a unique backdrop for holiday rentals, with many properties enjoying breathtaking views of the sea. In the vicinity, you can find charming cottages and contemporary beach houses equipped with amenities such as open-plan living spaces, private gardens, and easy access to the beach for those lazy summer days.

Additionally, the nearby village of West Bay, known for its picturesque harbour and dramatic cliffs, presents further options for beach house rentals. Here, visitors can expect properties with features like outdoor seating areas, BBQ facilities, and modern kitchens, great for family gatherings or a relaxing holiday with friends. The area also boasts local shops and eateries, providing convenience for guests.

For those looking to explore beyond the beach, the Jurassic Coast World Heritage Site is just a short drive away, offering spectacular walking trails and opportunities for fossil hunting. Many rentals in the Portland area are designed to enhance the coastal experience, with some featuring amenities like surfboards for hire or storage for bicycles, suiting active travellers eager to explore the beautiful surroundings. Find your rental near the beach in Portland.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, cottages are the most popular type of holiday rental, with around 288 available across the area. These charming properties are often located in picturesque settings, superb for a tranquil getaway. Most cottages come equipped with fully functional kitchens, cosy living areas, and outdoor spaces, ideal for enjoying the coastal views and fresh air.

Additionally, there are about 56 holiday houses, which cater well to families or larger groups, featuring multiple bedrooms and often private gardens or patios for relaxation. For those seeking a more urban experience, approximately 32 apartments are available, typically located near local amenities and attractions. These units usually offer modern conveniences such as kitchen facilities and comfortable seating areas.
Are there any family house rentals in Portland?
In Portland, there are numerous family-friendly house rentals available, with around 49 options to choose from. This charming town, located along the Jurassic Coast, offers a variety of accommodations suitable for families looking to enjoy their seaside getaway. Many of these properties boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.

Visitors will appreciate the close proximity to stunning attractions such as the Portland Bill Lighthouse and the picturesque Chesil Beach, great for beach outings and picnics. Additionally, some homes may feature amenities like game rooms or gardens, providing entertainment for all ages.
Can I rent a holiday home with a pool or hot tub in Portland?
In Portland, England, there are several holiday homes available for rent that feature pools and hot tubs, offering a delightful retreat for travellers. The charming coastal town provides a picturesque backdrop, with many properties located near the scenic Jurassic Coast, a UNESCO World Heritage Site known for its stunning cliffs and fossil-rich beaches.

Travellers can expect a variety of amenities in these rentals, including private swimming pools, relaxing hot tubs, and spacious outdoor areas for al fresco dining. Many homes come with fully equipped kitchens, allowing guests to prepare their own meals, and comfortable living spaces for unwinding after a day of exploration.
Can I find long-stay holiday rentals in Portland?
A long-stay holiday rental in Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Portland?
In Portland, there are several pet-friendly house rentals available, with a total of around 42 options for travellers to choose from. Many of these holiday homes are situated in charming locations that provide easy access to the beautiful countryside and coastal areas. Guests can expect amenities such as fully equipped kitchens, spacious living areas, and private gardens, making them ideal for families or groups travelling with pets.

The town itself is well-positioned for exploring the stunning landscapes of the Jurassic Coast, where pets are often welcome on various trails and beaches. Additionally, the surrounding areas offer picturesque walks and scenic spots that are great for pet owners looking to enjoy the outdoors.
Are there any remote work holiday rentals in Portland?
In Portland, England, there is a substantial selection of remote work holiday rentals available, with around 376 options to choose from. Many of these properties are equipped with essential amenities tailored for remote workers, including reliable Wi-Fi in both public areas and within individual rooms. This ensures that guests can stay connected and productive during their stay.

The town is known for its picturesque coastal scenery and historic landmarks, making it an appealing destination for those looking to blend work with leisure. Accommodations often feature comfortable workspaces, allowing for a conducive environment to focus on tasks while enjoying the tranquil surroundings.

Additionally, Portland offers easy access to local attractions, such as the iconic Portland Bill Lighthouse and the stunning Chesil Beach, providing a great backdrop for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Portland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Portland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Portland?
In Portland, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties are located near the beach, making it easy for visitors to enjoy coastal activities. Additionally, a number of rentals permit pets, ensuring that travellers can bring their furry companions along. For those with service animals, these accommodations are also accommodating. Free WiFi is commonly available, enabling guests to stay connected during their stay.
When is the best time to visit Portland for a holiday rental?
August is the most popular time to visit Portland, offering a vibrant setting that attracts holidaymakers eager to explore the charming streets and coastal beauty of this historic town. During the peak season, which spans from June to August, visitors can enjoy warm temperatures averaging around 18 to 22 degrees Celsius, superb for outdoor activities and leisurely sightseeing.

The summer months are particularly lively, with plenty of events, festivals, and activities taking place. Whether you're strolling along the picturesque shoreline or indulging in the local culinary scene, there are endless opportunities to immerse yourself in Portland's unique character and scenic surroundings.

If you're looking for a more budget-friendly time to visit, consider coming in December. Although it's part of the low season, the festive atmosphere during this month can be quite enchanting, with holiday decorations and local markets adding to the charm. You may find great value in holiday rentals, allowing you to experience Portland's winter wonderland without the summer crowds.

Ultimately, the best time to book a holiday rental in Portland hinges on your preferences—whether you seek the bustling energy of summer or the quieter, cosy charm of winter.
How early should I book a Portland holiday rental?
Book your Portland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Portland?
In Portland, England, visitors can explore a variety of attractions that highlight the area's natural beauty and maritime heritage. The iconic Portland Bill Lighthouse, located at the southern tip of the island, offers stunning coastal views and is a popular spot for photography. Nearby, the unique rock formations of the Jurassic Coast, a UNESCO World Heritage Site, provide opportunities for fossil hunting and scenic walks along the cliffs.

The Nothe Fort, a Victorian coastal artillery fort, offers fascinating insights into the region's military history and stunning views over Weymouth and the coastline. For those interested in marine life, the Portland Marina provides access to sailing, boating, and other water activities.

In the heart of the island, the village of Fortuneswell features quaint shops and local eateries, while the surrounding countryside offers beautiful walking trails, such as those on the South West Coast Path, allowing visitors to immerse themselves in the area's natural landscapes.
Can I change or cancel my Portland home rental booking on Vrbo?
To find Portland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Portland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas