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Holiday houses in South Portland

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Top-rated holiday rentals in South Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Apartment in Portland

4.82 out of 5 average rating, 354 reviews

Spacious and Comfortable Private Apartment

Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!

14 – 21 Jan

Guest favourite

Apartment in Gorham

4.96 out of 5 average rating, 195 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Enjoy the historical charm of one of Gorham's oldest homes. Come stay in a lovely private second floor, one bedroom apartment with private entry. Just walking distance from restaurants, the grocery store, laundromat, college campus and local trails. It offers private off-street parking for one car and it is located in the heart of Gorham village, a safe and family oriented community. Private bedroom with queen size bed and a full size futon provided. No backyard access. Full Kitchen. Full bath.

23 – 30 Oct

$1,380 AUD total

Guest favourite

Apartment in South Portland

4.89 out of 5 average rating, 199 reviews

Willard Square - The View

“So much bigger than in the photos.” A charming apartment in the Willard Beach neighborhood of South Portland, Maine. There are bakeries, ice-cream parlor and restaurants within walking distance. Easy access to Portland , Midcoast airport. The area has many local craft breweries and award winning restaurants. This apartment is the perfect spot to stay for your Maine vacation. It is a great walking neighborhood with many attractions nearby, but you might want a car for getting around the area. I

15 – 22 Jan

$2,192 AUD total

Guest favourite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Love gardens, pine trees, campfires, and birds? Curious about tiny homes? Our 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping the beverage of your choice from your private deck. It will be a unique and amazing experience and one you will remember! Bonus: 2 super friendly dogs and a cat that will be around the property during your stay. New in 2024: A/C!!STHR-000718-2018

19 – 26 Sept

$1,765 AUD total

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 114 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

23 – 30 Oct

$1,217 AUD total

Guest favourite

Guest suite in Scarborough

4.98 out of 5 average rating, 139 reviews

Beautiful, private apartment!! Great location!

Beautiful 750 square foot in-law apartment with private entrance. Full bedroom, bathroom, kitchen (including dishwasher), washer/dryer, and garage parking. Free wi-fi, cable, and Netflix included! All essentials included in addition to beach towels, chairs, table & cooler for the beach. Private patio includes a grill for use as well (weather permitting). Great location - 10 minutes to downtown Portland, 15 minutes to multiple beaches, 5 minutes to mall & restaurants.

23 – 30 Jan

$1,530 AUD total

Guest favourite

Apartment in South Portland

4.91 out of 5 average rating, 149 reviews

Sunny and beautiful brick house apartment

This beautiful and cozy apartment was renovated by our own hands, with energy efficiency and craft in mind. The space is an opened kitchen/living room with 2 bedrooms. Reclaimed beams and old wood mix with fun colors and gorgeous full sunlight. A lush organic garden surrounds the house with backyard chickens. Set on a quiet street, walking distance to Willard Beach & Scratch bakery, 5 minutes to Portland Headlight and 10 minutes to Portland's Old Port.

27 Oct – 3 Nov

$2,009 AUD total

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 173 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

4 – 11 Mar

$1,259 AUD total

Guest favourite

Guesthouse in Cape Elizabeth

4.98 out of 5 average rating, 140 reviews

Newly built private guest suite off Shore Road

Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.

21 – 28 Apr

$1,974 AUD total

Guest favourite

Apartment in Portland

4.94 out of 5 average rating, 457 reviews

No cleaning fee! Location, location! And parking!

At Location Location! You can be assured that we take care of all the cleaning… so please be on vacation! This lovely, simple 1 bedroom apartment is in the heart of the Portland's West End. Just around the corner, a foodie paradise! Zu bakery, Chaval, Pan Men Miyake, Tandem bakery, El Corazon and Local 188 many others. Just down the street, Maine Med,Mercy Hospital, PMA, art galleries, shopping & the Old Port!

19 – 26 Nov

$1,127 AUD total

Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 153 reviews

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

1 – 8 Jan

$1,221 AUD total

Guest favourite

Loft in South Portland

5.0 out of 5 average rating, 109 reviews

Serene studio apartment, close to everything.

Welcome to South Portland! Your spacious studio apartment with private entrance is a short walk to Fore River Brewing, Lincoln & Main/Electric Bike Cafe & Winery and the Greenbelt Walkway. A 10-min Uber ride will take you to the Old Port and South Portland staples like Willard Beach and Scratch bakery.

27 Apr – 4 May

$1,907 AUD total

Holiday rentals for every style

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Popular amenities for South Portland holiday rentals

Free parking on premises

Air conditioning

Stay near South Portland's top sights

The Maine Mall86 locals recommend

Portland International Jetport50 locals recommend

Fort Williams Park229 locals recommend

Thompson Point28 locals recommend

Portland Museum of Art412 locals recommend

Casco Bay Lines87 locals recommend

Other great holiday rentals in South Portland

Guest favourite

Guesthouse in Windham

5.0 out of 5 average rating, 219 reviews

Cottage on Black Brook Preserve

29 May – 5 June

$1,544 AUD total

Guest favourite

Apartment in South Portland

4.95 out of 5 average rating, 255 reviews

Stylish Studio Apt with Parking

16 – 23 July

$2,416 AUD total

Guest favourite

Guest suite in Saco

4.94 out of 5 average rating, 382 reviews

Barn-Board Abode (private studio) powered by solar

26 Feb – 5 Mar

$1,320 AUD total

Guest favourite

Cottage in Scarborough

4.97 out of 5 average rating, 161 reviews

Bright, clean, private cottage near Higgins Beach!

31 Jan – 7 Feb

$1,855 AUD total

Guest favourite

Condo in Portland

4.85 out of 5 average rating, 207 reviews

Old Port on foot-additional parking option avail

31 Oct – 7 Nov

$1,458 AUD total

Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 549 reviews

Charming West End Hideaway. Private Parking

4 – 11 Nov

$1,900 AUD total

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 198 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

8 – 15 Nov

$1,274 AUD total

Apartment in Portland

4.78 out of 5 average rating, 305 reviews

Studio w/ Patio, Sauna & Onsite Massage

11 – 18 Sept

$1,397 AUD total

Quick stats about accommodation in South Portland

Total rentals
540 properties
Rentals with dedicated workspaces
280 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
150 properties allow pets
Family-friendly rentals
260 properties are a good fit for families
Total number of reviews
57K reviews

Destinations to explore