
Holiday rentals with a pool in Portland
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Top-rated rentals with a pool in Portland
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House rentals with a pool

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.

Lovely home with hot tub and pool
I had a wonderful stay., they were fantastic in accommodations for me and my service dog who loved the yard. The home is beautiful and the host was very accommodating. communication was great. I look forward to staying there when I’m in that area again.

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.

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.

Kennebunk's Charming Beach Home
We had a wonderful stay. The house was spotless and beautiful with a fully stocked kitchen, super comfortable beds, and great amenities. Our kids loved the heated pool , hot tub, board games, and the easy walk to the beach. The location is also great and close to lots of restaurants and shopping. Stephanie was very kind, helpful, and quick to respond to any questions.

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
We loved our stay at The Lazy Lobster!! Andrew was a very communicative host. He thought of every possible thing we might need help with before we even knew we needed it! The house was beautiful and included every amenity we needed and details were well thought out. We especially enjoyed playing games in the living room, hanging in the hot tub/pool, and the wagon to carry all of our gear to the beach. It was the perfect stay for a group beach trip!

Maine Pondfront Home Sleeps 22 - Pool & Hot Tub
The place is beautiful! The pictures don’t do it justice. Alexander is very responsive and friendly, and will answer any questions you might have! The house was clean, the game room was enough to fit everyone in our group! We came here to celebrate my husband’s birthday and it met all our expectations! We will definitely come back again.
Condo rentals with a pool

Lovely 1 Bedroom condo with amazing ocean view
Marko was outstanding with responses and caring about our stay. The location is perfect.. walking distance to everything! And the VIEW was more beautiful than the photos!

Footbridge Escape A Comfy Condo w/ Pool, the Beac
Great location -- perfect for a "work away from home" week or an autumn visit -- hosts four adults super comfortably, location is great. Third year in a row and we always come back to here!

Ogunquit one bedroom walk to beach
Great location and spacious one bedroom suite with hot tub! InnSeason Resorts is not in downtown Ogunquit but we walked there in about 20 minutes, which we didnt mind. Footbridge Beach is less than a 10 minute walk away. There are many restaurants, shops and markets close by mostly by car but also two restaurants right next to the resort! I didn’t expect such a spacious place. The bedroom is large with a king size bed and ensuite hot tub and sink (the bathroom has its own sink as well). The kitchen has everything one can possibly need with a one burner portable stove. Katy was super responsive and helpful. The staff at the resort are also wonderful and accommadating. I highly recommend this for couples and parents with one or two kids!

Lovely Seaglass Studio, Pool, Walk to Everything!
Denise is an outstanding host! We couldn't believe that the kitchen was FULLY stocked! from the coffee keurig, to the teaspoons and everything one would need to cook dinner or breakfast or both. We were super impressed with the quality of kitchen items and how clean everything was. Even the bathroom was stocked with the "little things" like individual make up remover packs which I was most thankful for as I had forgotten mine! The linens were beautiful and there were 3 choices of pillows for the bed! We loved that she also had clear instructions regarding towels, checking out and the use of the keyless entry. The decor is warm and welcoming...very inviting. We loved that we could walk to everything in Ogunquit and Perkins Cove. Our stay in Maine was just wonderful and we would definitely book with Denise again.

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

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

2 Bdrm condo with a pool 1/2 mile from beach
Kate & Kate’s place was fantastic. The location was perfect for both enjoying the beach and fall weather, and also doing some shopping nearby. There are restaurants very close by as well. It was very clean, the beds are extremely comfortable, and the little things really stood out here- many towels, washer and dryer, all the things you need for your stay are provided and so appreciated. Excellent place to stay!!

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.
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
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
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- 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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