Portland holiday lettings

We found 677 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 24 homes, 76 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
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  • 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

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)
  • Fantasy Island Fun Park (6.4 mi / 10.3 km)
  • Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 km)
  • Kingston Maurward Park and Gardens (12 mi / 19.4 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.

Holiday Rental options in Portland