Holiday 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

Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 35 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

TrishRating, 5 stars1 week ago
we can't say enough about lovely our stay was at this beautiful house in OOB. the house is so clean and bright. its within walking distance to restaurants and stores. its right across from the heated pool. it really is such a gem!
Guest favourite
Home in Sebago
5 out of 5 average rating, 18 reviews

Treehouse Farm - Sebago

HollyRating, 5 stars1 month ago
Great backyard with a pool, hot tub, fire pit and privacy with the woods.
Superhost
Home in Windham
5 out of 5 average rating, 5 reviews

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More

KimRating, 5 stars3 weeks ago
We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!
Guest favourite
Home in Old Orchard Beach
4.9 out of 5 average rating, 10 reviews

Oceanfront Cottage 1

LoganRating, 5 stars2 months ago
We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars8 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 Fryeburg
4.97 out of 5 average rating, 30 reviews

The Lodge at Hidden Pines

JordannaRating, 5 stars3 months ago
The house was exactly as described and seen in the photos, a large, beautiful, authentic log cabin in the woods. The setting was quiet and beautiful though conviently right off the main road. We enjoyed cross country skiing, ice skating and a sleigh ride in Jackson (about 30 min away) and shopping in North Conway (about 20 min). Eileen made sure we were plowed and shoveled regularly during the snow storm so we enjoyed curling up by the fire and watching a movie on the large tv. My mother in particular enjoyed all the vintage decor which brought back childhood memories.
Top Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 40 reviews

Our Beach House Getaway

JenniferRating, 5 stars9 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.
Guest favourite
Home in Wells
5 out of 5 average rating, 51 reviews

2BR, Sea & Relax w/ Wells Reserve View

SamiraRating, 5 stars3 weeks ago
Jordanna’s place was beautiful and cozy! Perfect for a small family or girls trip up to 3 people. Place was spotless, lots to do in the area and will close proximity to Ogunquit and Kennebunkport. Would go back anytime!

Condo rentals with a pool

Top Guest favourite
Condo in Wells
4.97 out of 5 average rating, 30 reviews

Cozy Beach Condo in Wells - Hot Tub & Pool!

EmilyRating, 5 stars3 weeks ago
Kathleen’s Ogunquit Airbnb is perfect! She has thought of everything you may need and more. Kathleen was responsive when needed and communicated helpful details throughout our stay. The location is fantastic and made exploring the Maine coastline very convenient. Thank you, Kathleen!!!
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 favourite
Condo in Ogunquit
4.98 out of 5 average rating, 46 reviews

Pretty Boutique Studio, Pools, Walk to Everything!

MollyRating, 5 stars7 months ago
This was a great place to stay! My husband and I were very happy. Highly recommend!!
Guest favourite
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
Guest favourite
Condo in Wells
4.95 out of 5 average rating, 101 reviews

Relaxing Beachside Condo with Pool at Wells Beach

MaryRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Conway
4.96 out of 5 average rating, 110 reviews

Cozy, clean, 2nd floor condo in Conway, NH!

RachelRating, 5 stars5 months ago
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!
Top Guest favourite
Condo in Conway
4.95 out of 5 average rating, 21 reviews

Harmony Hideaway - A Tranquil Getaway on the Saco

LonRating, 5 stars3 months ago
Condo was clean, well stocked, and comfortable for our family on a winter stay. Clear instructions for making the stay comfortable and easy. A very easy drive to a restaurants, activities, and anything you’d need. Would stay again!
Guest favourite
Condo in Conway
4.92 out of 5 average rating, 122 reviews

Cozy Family Retreat with Saco River Access

JeanineRating, 5 stars3 months ago
Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.

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