Discover a selection of 99 vacation rentals in Parkside, Portland that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and parking. Prices start at $119 per night, and houses and condos are popular options for a stay in Parkside. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Parkside
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What are the top vacation rentals in or near Parkside?

Whatever you're looking for in a getaway, you'll find a rental in or around Parkside that's a perfect match. Here are some of our favorites:

  • Around 1 mile from the center of Parkside, it's hard to top "Henry” Penthouse Suite: Amazing Views". It has 2 bedrooms and a range of amenities including a nearby waterfront and cable/satellite TV services.
  • Alternatively, make a booking at "Chic One Bedroom Apartment In Portland's Arts District". Located around 0.1 miles from the heart of Parkside, it has 1 bedroom and features cookware, dishware and utensils and a kitchen.

For even more great options, use the search bar at the top of the page to find the perfect Parkside vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Parkside?

Clock out on Friday and then forget the real world. If it's time for some fun and relaxation, these retreats in and near Parkside promise the ideal weekend getaway:

  • "Percival” Penthouse Suite: Breathtaking Views" is a comfortable option around 1 mile east of central Parkside. You'll never need to venture far to find something interesting to do around this property. Get out and visit Casco Bay and Kennebunkport Harbor. Activities like fishing and windsurfing will perfectly round off your weekend trip.
  • Alternatively, unpack your bags at "Margaret” Penthouse Suite: Amazing Views Of Casco Bay". Approximately 1 mile east of Parkside, fun activities around here include windsurfing and hiking and biking. Rather see the sights? Make a beeline for Winslow Memorial Park and Little Watchic Pond.

Can I find studio apartments for rent in and around Parkside?

Get a taste of the culture and atmosphere of Parkside from the privacy and comfort of your own studio apartment. Whether you're looking to kick back on your own or live it up with a few friends, you'll find the ideal studio apartment in and around Parkside:

  • Unpack your suitcase at "Chic One Bedroom Apartment In Portland's Arts District". Amenities including golf and shopping will make you feel right at home here.
  • Another popular option is "Historic Condo With Casco Bay Views". Take advantage of a stovetop, air conditioning and other conveniences during your stay.

There are loads of highlights around Parkside to put on your must-do list. Nourish the culture vulture in you with a visit to Port City Music Hall and Space Gallery.

Can I find short term rentals in or near Parkside?

Now and then, you just need to take a break from the real world, even if it's only for one or two days. Experience a delightful combination of relaxation and adventure at one of these short-term rentals in or around Parkside:

  • If you want to be close to the action, "Historic Condo With Casco Bay Views" will suit your style. It's within reach of the heart of Parkside and an excellent base to check out sights like Portland Museum of Art and University of Southern Maine.
  • Eat, sleep and explore what's around you from "Spacious 3 Bed In A Prime Old Port Location", another excellent option. Victoria Mansion and Children's Museum of Maine should be on your must-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Parkside?

Whether spent in a cottage, a cabin or a condo, a romantic weekend getaway is one of the best ways to say "I love you." Whisk your sweetheart off for a couple of leisurely days at one of these popular escapes in or near Parkside:

  • Sneak away on Friday afternoon for a couple of passion-filled nights at "Henry” Penthouse Suite: Amazing Views". Located around 1 mile from Parkside, it comes with plenty of nice touches, like a nearby bay and winery tours.
  • "Chic One Bedroom Apartment In Portland's Arts District" is another retreat that's sure to impress. It's about 0.1 miles from Parkside and has winery tours and a nearby bay.

What are the best large group vacation rentals in or near Parkside?

Big groups mean gigantic fun. They also mean finding someplace that'll effortlessly fit your whole squad. Browse our large group vacation rentals in or around Parkside and get your loved ones together under the same roof:

  • There's plenty of room to move at "Stunning 2nd And 3rd Floor Apts - Usm Area". Around 1 mile northwest of Parkside, this impressive retreat has 8 bedrooms that sleep up to 18 guests. It comes with a host of amenities, including a kitchen and high-speed internet services.
  • "Two Beautiful Apartment" is another fantastic option. It's around 1 mile to the northwest of Parkside, has 4 bedrooms and accommodates up to 12 guests. A kitchen and off-street parking options are just a couple of things designed to make your stay more comfortable.

What are the best houses for rent with a pool in or near Parkside?

Having access to a pool is always a nice perk when you're on vacation, especially if you're taking the kids. Splash the days away at one of these houses with a pool in or near Parkside:

  • Pack your swimsuit and goggles and enjoy a fun stay with your group at "Maine Getaway: Bright Beautiful Back Cove House Near Woodfords Corner And Old Port". Other amenities here include towels and childrens activities.
  • Alternatively, stay at "The Globe House On Munjoy Hill" and spend your days poolside. A garden and nearby birdwatching activities are other things your crew will like about this vacation home.

What are the best large family vacation rentals in or near Parkside?

Every family get-together should be one to remember. Whether you're organizing some time off with the kids or a reunion with the extended family, our large family vacation rentals in or near Parkside offer a home away from home with plenty of space for everyone:

  • Around 1 mile to the southeast of Parkside, "Upscale Large 3 Bedroom Within Walking Distance To Everything" has 3 bedrooms and sleeps up to 8 guests. It comes with a host of amenities, including coffee and tea making facilities and free toiletries.
  • Another great option is "Upscale, Urban Retreat". This large rental is 1 mile southeast of Parkside and comes with a separate dining area, towels and more. With 5 bedrooms accommodating up to 11 people, don't worry about leaving anyone off your guest list.

When you want to venture outside and explore, there are plenty of family-friendly attractions in the area to keep everyone happy. Children's Museum of Maine, Portland Observatory and Southworth Planetarium should be top of your must-do list.

Are there one-bedroom vacation rentals in or near Parkside?

Idyllic romantic retreats, business trips or solo adventures — a one-bedroom vacation rental is a perfect solution for all sorts of occasions. One of our options in or near Parkside is sure to impress:

  • Book "Chic One Bedroom Apartment In Portland's Arts District" for a couple of days. This one-bedroom vacation property features a kitchen and a swimming pool and is close to the center.
  • Or maybe "Historic Condo With Casco Bay Views" is more your style. Another conveniently located one-bedroom option, this place comes with a kitchen, an ocean view and more.

Can I find two-bedroom vacation rentals in or near Parkside?

At Vrbo, we've got rental properties in or near Parkside to suit just about everyone. Here are a couple of our favorite two-bedroom options to consider:

  • With a nearby waterfront and a kitchen, "Henry” Penthouse Suite: Amazing Views" has all you'll need for an awesome stay. Settle in and then venture out and explore the area.
  • Another popular option is "Percival” Penthouse Suite: Breathtaking Views". With amenities such as a water view and a nearby waterfront, you'll have no trouble making yourselves at home here. Choose your favorite room, unpack your suitcases and let the good times roll!