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 Kennebunk
4.81 out of 5 average rating, 114 reviewsKennebunk/Kennebunkport Beach House w/Pool!
17–24 Mar
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
31 May – 7 Jun
Home in Conway
4.92 out of 5 average rating, 200 reviewsThe Sugar Shack - A sweet spot in the Village
13–18 May
Home in Portland
4.94 out of 5 average rating, 70 reviews"Good Vibes" 4 Wonderful Seasons @ Portland Home!
7–14 Feb
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
5–12 Dec
Home in Wells
5.0 out of 5 average rating, 25 reviews2BR, Sea & Relax w/ Wells Reserve View
6–13 Oct
Condo rentals with a pool
Condo in Conway
4.92 out of 5 average rating, 105 reviewsCozy Family Retreat with Saco River Access
3–10 May
Condo in Bartlett
4.98 out of 5 average rating, 113 reviewsSki season is booking now! Perfect for 2 families!
14–21 Feb
Condo in Conway
4.99 out of 5 average rating, 154 reviews3BR, 2BA condo in No. Conway, Close to everything!
16–23 Mar
Condo in Intervale
5.0 out of 5 average rating, 50 reviewsCozy stays with Breathtaking views!
15–22 Dec
Condo in Wells
4.86 out of 5 average rating, 28 reviewsDrake's Island Beach Area Studio
12–19 Sep
Condo in Ogunquit
4.96 out of 5 average rating, 25 reviewsLovely Studio, Walk Everywhere, .5 mi-town, Pool!
24–31 Jul
Condo in Wells
4.95 out of 5 average rating, 81 reviewsNewly Renovated Coastal Condo Steps To Wells Beach
17–24 Jun
Condo in Intervale
4.9 out of 5 average rating, 42 reviewsMountain Condo minutes from North Conway
6–13 May
Quick stats about holiday rentals with a pool in Portland
Total rentals
70 properties
Wi-Fi availability
70 properties include access to Wi-Fi
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
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