Holiday rentals with a pool in Portland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Portland
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Portland rentals with a pool
House rentals with a pool
Home in Portland
4.94 out of 5 average rating, 70 reviews"Good Vibes" 4 Wonderful Seasons @ Portland Home!
17–24 Oct
Home in Wells
4.9 out of 5 average rating, 10 reviewsCottage in Wells Maine
29 Sep – 6 Oct
Home in Wells
4.97 out of 5 average rating, 65 reviewsModern, convenient, marsh side cottage
30 Aug – 6 Sep
Home in Portland
4.82 out of 5 average rating, 98 reviewsThere's No Place Like Home
18–25 Dec
Home in Old Orchard Beach
5.0 out of 5 average rating, 55 reviewsOOB Oasis - 5BR private Retreat w/ Pool
16–23 Feb
Home in Old Orchard Beach
5.0 out of 5 average rating, 44 reviewsThe Happy Cottage
9–16 Jun
Home in Kennebunk
4.82 out of 5 average rating, 22 reviewsKennebunk's Charming Beach Home
1–8 May
Home in Standish
4.95 out of 5 average rating, 40 reviews6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK
17–24 Feb
Apartment rentals with a pool
Apartment in Wells
4.86 out of 5 average rating, 28 reviewsDrake's Island Beach Area Studio
12–19 Sep
Apartment in Ogunquit
4.96 out of 5 average rating, 25 reviewsLovely Studio, Walk Everywhere, .5 mi-town, Pool!
23–30 Sep
Apartment in Wells
5.0 out of 5 average rating, 15 reviewsNEW Wells Beach Condo Steps to the Ocean with Pool
4–11 Sep
Apartment in Wells
4.89 out of 5 average rating, 70 reviewsStarfish Condo Wells Beach
16–23 Dec
Apartment in Old Orchard Beach
4.84 out of 5 average rating, 19 reviewsCHowder Ocean Oasis @ Old Orchard Beach
20–27 Jul
Apartment in Old Orchard Beach
4.81 out of 5 average rating, 32 reviewsGorgeous OceanView condo at Grand Victorian - #301
26 Sep – 3 Oct
Apartment in Old Orchard Beach
4.83 out of 5 average rating, 6 reviews30 second walk to Beach- Pool-Outdoor Shower
15–22 Mar
Apartment in Old Orchard Beach
4.89 out of 5 average rating, 9 reviewsGrand Victorian Ocean Rentals Oob310
21–28 Nov
Quick stats about holiday rentals with a pool in Portland
Total rentals
70 properties
Wifi availability
70 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2.7K reviews
Destinations to explore
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