Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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

Superhost

Flat in Portland

4.82 out of 5 average rating, 347 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!

9–16 Mar

$88 SGD per night
Guest favourite

Guest house in Portland

4.95 out of 5 average rating, 278 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

25–30 Apr

$214 SGD per night
Guest favourite

Flat in Portland

4.97 out of 5 average rating, 475 reviews

Amazing Views! Perfect Location. Loft style feel.

Oh the VIEW! City views and a beautiful park like old cemetery. Cozy, sunny private apartment in a quiet, Owner Occupied building. Perfect East End location for exploring all of Portland Just 2 blocks from Duckfat, Eventide and many restaurants, breweries and distilleries Comfy living room with a 55" TV and seating to take in the view. Fully equipped eat in kitchen, tile shower and a wonderful King size bed to watch the sun rise Includes Reserved Off street parking. License #STHR-000980

4–11 Apr

$184 SGD per night

Popular amenities for Portland holiday rentals

Stay near Portland's top sights

The Maine Mall86 locals recommend
Peaks Island176 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Portland Observatory132 locals recommend
Allagash Brewing Company156 locals recommend

Other great holiday rentals in Portland

Superhost

Flat in Scarborough

4.85 out of 5 average rating, 433 reviews

Tiny Pine Point Beach Pad - comfy, cozy surf shed

13–20 Apr

$143 SGD per night
Guest favourite

Loft in South Portland

5.0 out of 5 average rating, 105 reviews

Serene studio apartment, close to everything.

21–26 Apr

$186 SGD per night
Superhost

Flat in Portland

4.88 out of 5 average rating, 374 reviews

Modern East End studio, perfect Portland home base

31 Oct – 7 Nov

$170 SGD per night
Guest favourite

Flat in Portland

4.85 out of 5 average rating, 437 reviews

Cozy, Private Apartment

11–18 Nov

$160 SGD per night
Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 150 reviews

Joyful Munjoy Hill Garden Suite

$120 SGD per night
Guest favourite

Guest suite in Freeport

4.96 out of 5 average rating, 114 reviews

Solar Suite surrounded by Nature

23–30 Nov

$164 SGD per night
Guest favourite

Cabin in Lovell

4.98 out of 5 average rating, 246 reviews

Secluded, cozy cabin nestled in the Maine woods

13–20 Sep

$153 SGD per night
Guest favourite

Cottage in Scarborough

4.85 out of 5 average rating, 279 reviews

Charming beach cottage

22–29 Apr

$151 SGD per night
Guest favourite

Flat in Portland

4.82 out of 5 average rating, 191 reviews

Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom

29 Nov – 6 Dec

$209 SGD per night
Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 159 reviews

"Cornelia" Penthouse Waterfront Suite

12–19 Jan

$566 SGD per night
Guest favourite

Flat in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

17–24 Apr

$153 SGD per night
Guest favourite

Flat in Arundel

4.91 out of 5 average rating, 125 reviews

Ginger Hilltop

4–11 Mar

$145 SGD per night

Quick stats about holiday rentals in Portland

Total rentals

1.5K properties

Rentals with dedicated workspaces

770 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

390 properties allow pets

Family-friendly rentals

780 properties are a good fit for families

Total number of reviews

151K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland