Vacation rentals with a pool in South Portland

Find and book unique homes with a pool on Airbnb

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Popular amenities for South Portland rentals with a pool

House rentals with a pool

Top guest favorite
Home in Sebago
5 out of 5 average rating, 19 reviews

Treehouse Farm - Sebago

TheresaRating, 5 stars4 days ago
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.
Superhost
Home in Old Orchard Beach
4.82 out of 5 average rating, 11 reviews

Oceanfront Cottage 1

LoganRating, 5 stars3 months ago
We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!
Guest favorite
Home in Bridgton
4.89 out of 5 average rating, 9 reviews

Peaceful Retreat

CarolRating, 5 stars4 months ago
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.
Guest favorite
Home in Wells
5 out of 5 average rating, 53 reviews

2BR, Sea & Relax w/ Wells Reserve View

KatherineRating, 5 stars1 week ago
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.
Superhost
Home in Kennebunk
4.81 out of 5 average rating, 43 reviews

Kennebunk's Charming Beach Home

BrennaRating, 5 stars3 weeks ago
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.
Superhost
Home in Arundel
5 out of 5 average rating, 4 reviews

Spectacular 3 Bed Resort Cottage

JaimeRating, 5 stars2 days ago
This cottage in Arundel was just perfect! Beautiful, private, quiet setting, and just a short drive to all the best beach towns! We absolutely loved everything about it! Jaime & Susan
Top guest favorite
Home in Ogunquit
5 out of 5 average rating, 64 reviews

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

ErinRating, 5 stars3 days ago
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!
Guest favorite
Home in Portland
5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

DanielRating, 5 stars7 months ago
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

Condo rentals with a pool

Superhost
Condo in Ogunquit
4.74 out of 5 average rating, 19 reviews

Lovely 1 Bedroom condo with amazing ocean view

FrankRating, 5 stars10 months ago
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!
Superhost
Condo in Ogunquit
4.67 out of 5 average rating, 3 reviews

Footbridge Escape A Comfy Condo w/ Pool, the Beac

JimRating, 5 stars20 months ago
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!
Superhost
Condo in Ogunquit
5 out of 5 average rating, 3 reviews

Ogunquit one bedroom walk to beach

MimiRating, 5 stars11 months ago
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!
Guest favorite
Condo in Wells
4.85 out of 5 average rating, 188 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 weeks ago
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
Guest favorite
Condo in Wells
4.91 out of 5 average rating, 92 reviews

Starfish Condo Wells Beach

WendyRating, 5 stars1 month ago
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
Superhost
Condo in Wells
4.69 out of 5 average rating, 32 reviews

2 Bdrm condo with a pool 1/2 mile from beach

JessicaRating, 5 stars8 months ago
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!!
Superhost
Condo in Wells
4.71 out of 5 average rating, 7 reviews

Awesome get away spot in Wells!

ManuelaRating, 5 stars8 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
4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars1 month ago
Great place to stay for our family of 4. I asked for 3 beds and that request was made possible. I enjoyed the area and it was quiet and peaceful place to rest after walking around the beaches and or state parks. Amenities were very good and communication with the check in team was excellent.

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