Holiday rentals with a pool in Portland

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Portland rentals with a pool

House rentals with a pool

Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 33 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

LoriRating, 5 stars8 months ago
Heather’s place was by far the most well maintained and clean Airbnb our family has ever stayed in. She was responsive and kind with all our needs. The pool was conveniently located right across the road and a beautiful place to spend the warmer day. Walking to the OOB trolly, seafood restaurants and the best ice cream place we’ve visited yet. We look forward to making Heather’s place and a trip to the Maine coast an annual family vacation.
Top Guest favourite
Home in Sebago
5 out of 5 average rating, 13 reviews

Treehouse Farm - Sebago

JasmineRating, 5 stars2 days ago
We had a great stay. Our kids especially loved the hot tub and fire pit and the cozy bed upstairs. Beds were all very comfortable and clean. Host was responsive and left clear instructions. We would have loved to stay longer but it was still great just for one night.
Superhost
Home in Wells
5 out of 5 average rating, 3 reviews

210 Sea Castle Circle

VincentRating, 5 stars7 months ago
Very nice place, everything was clean and smelling good, we felt right at home! Comfortable beds except the single one which we could feel the springs. Expensive parking everywhere near the beach, be advised, but free parking at the house. Everyone at the place was friendly. The only thing mmissing would be coffee pods, for the rest, everything was there!
Guest favourite
Home in Old Orchard Beach
4.97 out of 5 average rating, 34 reviews

Upscale OOB Beach House | Seasonal Heated Pool

MichaelRating, 5 stars1 week ago
Great place and an even better host! Everything was seamless and I was able to contact Jason with no issues at all!
Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 58 reviews

The Happy Cottage w/Pool & Hot Tub

JanelleRating, 5 stars6 months ago
Beautiful little neighborhood! Loved the front porch to sit and drink coffee. Beds were comfortable. It was clean and very accurate descriptions. Close to highway to go to all the attractions.
Guest favourite
Home in Wells
4.97 out of 5 average rating, 78 reviews

Modern, convenient, marsh side cottage

JodiRating, 5 stars8 months ago
This is a serene cottage in a convenient but quiet location. Check-in was issued free and the owner gave us great restaurant and hiking recommendations. The cottage has great amenities and was very clean. Perfect size for 2 people. There are Adirondack chairs in the yard to relax in and enjoy the view of the marsh and Wells Beach. We enjoyed walking to Batson River Brewery and Congdon’s donuts. Wells Beach is a few minutes drive away, or about a 30 minute walk. We will definitely come back to this cottage!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars6 months ago
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Top Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 40 reviews

Our Beach House Getaway

JenniferRating, 5 stars8 months ago
It was exactly as the pictures on the website. I reached out to Linda prior to leaving. She was very responsive answered all my questions. Great memories made with the family this week. Would definitely come back again. The ease of getting in and out of old Orchard Beach was great. Was only a 3-4 min drive to the beach. The pool there was a huge hit with the grandkids as the ocean in Maine is never really that warm.

Condo rentals with a pool

Top Guest favourite
Condo in Wells
4.96 out of 5 average rating, 27 reviews

Cozy Beach Condo in Wells - Hot Tub & Pool!

BrianRating, 5 stars1 week ago
This was my first experience with AirB&B. I hope all my future bookings are as great an experience as this was. Only rating 5 stars cause there isn’t 6.
Superhost
Condo in Wells
4.5 out of 5 average rating, 6 reviews

>ONE MILE to Wells Beach< Barefoot | Beach Breeze

SharonRating, 5 stars8 months ago
This unit in Barefoot was conveniently on the first floor…very clean..and the kitchen was well equipped with anything we needed! The pool and community room and gym were terrific! We love this B&B and would love to rent it again the same week in 2025…thanks for a great vacation!
Guest favourite
Condo in Wells
4.91 out of 5 average rating, 90 reviews

Starfish Condo Wells Beach

Kay-LeeRating, 5 stars1 month ago
Danielle was an excellent host. super responsive, and flexible when we needed it ! the rental is lovely and was a joy to stay in. the area was quiet and private 😁
Superhost
Condo in Wells
4.71 out of 5 average rating, 7 reviews

Awesome get away spot in Wells!

ManuelaRating, 5 stars6 months ago
Lovely cottage with EVERYTHING you need (e.g, kitchen & bath items are very well stocked with many options - condiments, coffee/tea, hair dryer, towels, health & beauty products - you name it!)! The location is close to lovely attractions and eateries. We visited Lobster Pt. Lighthouse and took a cliff walk - beautiful views! Ogunquit beach is also close by. Highly recommend Hobbs Harborside Restaurant - great seafood! Diane was a very accommodating and responsive host! It was the perfect location for our weekend getaway.
Superhost
Condo in Wells
4.75 out of 5 average rating, 126 reviews

Generic Two Bedroom - Stair access only

Rose-MarieRating, 5 stars2 months ago
The condo was very clean, tasteful decorated. Beds were comfortable. Loved the big table to play games and the living room was cozy for the evening and morning chats. Pretty views.
Superhost
Condo in Wells
4.86 out of 5 average rating, 37 reviews

Drake's Island Beach Area Studio

EmilyRating, 5 stars7 months ago
This is my third year in a row staying at the Wells condo. It is has been amazing each year. The other residents are very welcoming and friendly, always waving and saying hi. So much to do and eat right on the main road, with a short distance to beaches. I will absolutely be back for a fourth year!

Quick stats about holiday rentals with a pool in Portland

  • Total rentals

    60 properties

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 properties include access to Wi-Fi

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland
  6. Rentals with pools