
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

Love OOB! NEW 3 BR, 2.5 BA Maine Home
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.

Treehouse Farm - Sebago
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.

210 Sea Castle Circle
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!

Upscale OOB Beach House | Seasonal Heated Pool
Great place and an even better host! Everything was seamless and I was able to contact Jason with no issues at all!

The Happy Cottage w/Pool & Hot Tub
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.

Modern, convenient, marsh side cottage
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!

Lovely home with hot tub and pool
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!

Our Beach House Getaway
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

Cozy Beach Condo in Wells - Hot Tub & Pool!
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.

>ONE MILE to Wells Beach< Barefoot | Beach Breeze
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!

Starfish Condo Wells Beach
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 😁

Awesome get away spot in Wells!
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.

Generic Two Bedroom - Stair access only
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.

Drake's Island Beach Area Studio
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
- Rentals with a hot tub Portland
- Kid-friendly rentals Portland
- Private suite rentals Portland
- Rentals with a washing machine and dryer Portland
- Apartment rentals Portland
- Rentals with outdoor seating Portland
- Cabin rentals Portland
- Cottage rentals Portland
- Pet-friendly rentals Portland
- Beach house rentals Portland
- Rentals with beach access Portland
- House rentals Portland
- Beachfront rentals Portland
- Rentals with an EV charger Portland
- Rentals with a sauna Portland
- Hotel rentals Portland
- Rentals with a patio Portland
- Family-friendly rentals Portland
- Condo rentals Portland
- Fitness-friendly rentals Portland
- Rentals with a fire pit Portland
- Rentals with a kayak Portland
- Rentals with breakfast Portland
- Townhouse rentals Portland
- Waterfront rentals Portland
- Villa rentals Portland
- Rentals with a fireplace Portland
- Rentals with pools Cumberland County
- Rentals with pools Maine
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Wells Beach
- Cranmore Mountain Resort
- Ogunquit Playhouse
- East End Beach
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- King Pine Ski Area
- Wentworth by the Sea Country Club
- Parsons Beach
- Portland Museum of Art
- Mothers Beach
- Crescent Beach
- Ferry Beach
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Dunegrass Golf Club
- Palace Playland
- Funtown Splashtown USA
- Things to do Portland
- Sports activities Portland
- Sightseeing Portland
- Art and culture Portland
- Tours Portland
- Nature and outdoors Portland
- Things to do Cumberland County
- Art and culture Cumberland County
- Food and drink Cumberland County
- Sightseeing Cumberland County
- Sports activities Cumberland County
- Tours Cumberland County
- Nature and outdoors Cumberland County
- Things to do Maine
- Sightseeing Maine
- Nature and outdoors Maine
- Sports activities Maine
- Tours Maine
- Food and drink Maine
- Things to do United States
- Tours United States
- Food and drink United States
- Entertainment United States
- Nature and outdoors United States
- Sightseeing United States
- Sports activities United States
- Art and culture United States
- Wellness United States