
Vacation rentals with a pool in Portland
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Top-rated rentals with a pool in Portland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Portland rentals with a pool
House rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home
Clean , comfortable...home away from home...would definitely rebook if I revisit Old Orchard Beach Elisa

Treehouse Farm - Sebago
We stayed for 2 nights in June, and we all wished we could have stayed longer. This house was perfect for 6 adults and 1 toddler as well as our 2 dogs. The house is absolutely beautiful, modern updated and very tastefully decorated. The kitchen and living room were a nice gathering area for us. We found the bedrooms comfortable and very peaceful for a good night sleep. The pool and outside was our favorite. The pool was perfect, clean & warm. We loved that it had a shelf that our toddler granddaughter could sit on and splash around. We didn't get to the fire pit, but that area was very nice as well. We had a great time, and we are hoping to get back again next year. We highly recommend this home and the host who was always easy to communicate with and highly responsive.

Peaceful Retreat
Aimee’s place was amazing! Absolutely gorgeous inside and out. So much attention to every detail. Aimee was quick to respond with any questions I had. The games provided great entertainment for the kids during a snowy day. I highly recommend. We can’t wait to come back.

Our Beach House Getaway
Amazing place to stay- clean and so nice inside (even nicer than the pictures). Great hosts great location. Would 100% stay again.

2BR, Sea & Relax w/ Wells Reserve View
Cottage 2 br, well equipped kitchen and nice extra porch enclosed and furnished beachy decor. Backyard comfortable adirondack chairs for sitting. Near to beach with free parking if spots are available. plenty of restaurants and grocery nearby. Last cottage in the row and was quiet. Pool and hot tub on property. Would rent again.

Maritime Meadows - Charming Resort-Style Home!
A beautiful home in a quiet neighborhood with everything you could need. Located a short distance from the beaches, towns, shopping and restaurants. We were here the last week of May when the crowds were not too bad. The weather was perfect—60’s and 70’s. The hosts are extremely responsive. Would definitely stay here again.

Heated Pool! Gorgeous Home Close to Kennebunkport
We had a great weeklong stay at the house. There was plenty of space both inside and out for us to dine, play and relax. We were 8 people across three generations and everyone enjoyed the house itself as well as the heated pool, BBQ and fire pit. Great location as it was 10 minutes into Kennebunkport and even less to a large supermarket in Kennebunk. We would definitely be more than happy to return in the future.

Cottage ten minutes from beach
Great place to stay! Clean and comfortable. Excellent location, close to many restaurants, and other activities!
Condo rentals with a pool

Cozy Beach Condo in Wells - Hot Tub & Pool!
Thank you for a great stay, Kathleen! My husband and I were celebrating our anniversary and both of our birthdays that week and needed a little get away. This was perfect for us. I wish the weather was better, but you can’t do anything about that. We ate great food, went to a movie, shopped, went to the Nubble lighthouse and more. We would definitely use Kathleen again. She also made arrangements to have my favorite hoodie sent back to me as I mistakenly left it on the back of the door. Great host and super cute place!

Stylish Designer Retreat on Langsford with Pool
My husband and I celebrate our anniversary by traveling somewhere and we really always try to find somewhere with the right balance of activities with a setting that helps us relax and reconnect.. this location and property was perfect for that. It is Located on a quiet street close enough to the hotspots but far enough to not be consumed by the traffic of visitors to the town. We even made friends with the neighbors. kennebunkport is a really nice town as well. For our anniversary, we were greeted with a sweet treat and the concierge service has been super attentive since booking to ensure we make the most of our stay. Unfortunately, the weather was not ideal To take advantage of the pool but it is such a great layout with a grill that we must return to enjoy it. Four nights and I was Still sad to leave. I’ll miss the night on the balcony of unit 2 and the ridiculously comfy bed. Thank you for everything.

Stars And Stripes
Absolutely our favorite place to stay!

Starfish Condo Wells Beach
This was a great find and enjoyed our 3 week there - We got to meet a few neighbors, and they were very nice as well - Very close to restaurants and Wells Beach - WIFI worked great as I work from home and the tip about leaving the second car at the Wells Transportation Center helped a lot ! Danielle was great with communication and rules - We would stay here again

Ocean View Studio Beach Condo
It was such a cozy, wonderful condo with ocean sounds and breezes right from the front door. Neighbors very kind and welcoming; never felt like a stranger from the first day! Although just a studio, quite spacious and very comfortable even when my husband and child came to visit! David always responded to any questions rather about the condo, condo building, or just a good place to eat! Just a lovely all around stay! All my classmates were jealous! :)

Relaxing Beachside Condo with Pool at Wells Beach
Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.

Cozy 1BR Condo near Beaches
My boyfriend and I had a blast at Jennifer’s place. The location is perfect and we loved swimming in the pool at the condo and the apartment’s cozy atmosphere. We would love to stay in another of Jennifer’s condos.

Seaside Condo w/stunning views, 2 Queen sized beds
I just got back from a wonderful stay at Baci Salati "Salty Kisses" condo at Belle of Maine. The condo is cute and cozy. It was very clean and has all the amenities needed. It is in a great location near restaurants, beaches and the grocery store. Evelyn is a wonderful host and was very easy to communicate with. I'm looking forward to staying there again in the future.
Quick stats about vacation 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
Wifi availability
60 properties include access to wifi
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- Surfside Beach
- Long Beach
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- Pemaquid Beach
- Coastal Maine Botanical Gardens
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- Fox Ridge Golf Club
- Wentworth by the Sea Country Club
- Ferry Beach
- East End Beach
- Brunswick Golf Club
- Pemaquid Point Lighthouse
- Palace Playland
- Cranmore Mountain Resort
- Crescent Beach
- Wolfe's Neck Woods State Park
- Purity Spring Resort
- King Pine Ski Area
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