Vacation rentals with a pool in Portland

Find and book unique homes with a pool on Airbnb

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Popular amenities for Portland rentals with a pool

House rentals with a pool

Guest favorite
A charming two-story home features a green-shingled exterior and a gabled roof. Large windows allow natural light to fill the interior. A white front door stands at the center, with a covered entryway. A fenced area is visible in the foreground, alongside designated parking spaces.
Home in Old Orchard Beach
5 out of 5 average rating, 33 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

LoriRating, 5 stars8 months ago
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.
Top guest favorite
A cozy outdoor area is illuminated by soft string lights and features circular seating around a stone fire pit. The backdrop showcases a charming two-story home nestled among trees, with warm light glowing from the windows, creating an inviting ambiance for evening gatherings.
Home in Sebago
5 out of 5 average rating, 13 reviews

Treehouse Farm - Sebago

JasmineRating, 5 starstoday
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.
Superhost
A bright and airy living space is highlighted by large glass sliders, allowing natural light to fill the room. A comfortable sofa, a wooden side table, and a television create a cozy atmosphere, while the adjoining dining area is visible through the glass, featuring a patterned rug.
Home in Wells
5 out of 5 average rating, 3 reviews

210 Sea Castle Circle

VincentRating, 5 stars7 months ago
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!
Guest favorite
A charming beach home features a pitched roof and warm red siding. The covered front porch is accented with white railings, providing a welcoming entrance. Bright windows enhance natural light, while a neatly landscaped area surrounds the home, contributing to its overall appeal.
Home in Old Orchard Beach
4.97 out of 5 average rating, 34 reviews

Upscale OOB Beach House | Seasonal Heated Pool

MichaelRating, 5 stars1 week ago
Great place and an even better host! Everything was seamless and I was able to contact Jason with no issues at all!
Guest favorite
A refreshing swimming pool is surrounded by a spacious concrete deck, featuring blue lounge chairs and striped umbrellas. The pool’s inviting turquoise water reflects the overcast sky, while a community center can be seen in the background.
Home in Old Orchard Beach
5 out of 5 average rating, 58 reviews

The Happy Cottage w/Pool & Hot Tub

JanelleRating, 5 stars6 months ago
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.
Guest favorite
The backyard features an above-ground pool surrounded by a spacious deck, offering ample seating and relaxation areas. A shaded dining space is visible under an umbrella, while the two-story colonial home stands in the background, framed by lush greenery.
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars6 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 favorite
A two-story cape-style home is featured, showcasing a welcoming front porch with two blue chairs and potted plants. The exterior includes light brown siding and a gray roof, surrounded by a well-maintained yard and ample parking space.
Home in Old Orchard Beach
5 out of 5 average rating, 40 reviews

Our Beach House Getaway

JenniferRating, 5 stars7 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 favorite
An aerial view captures a spacious community area featuring a large swimming pool surrounded by lounge chairs. Lush greenery envelops the setting, enhancing the tranquil atmosphere. A small pond reflects the landscape, with walking paths guiding residents between the pool and neighboring homes.
Home in Arundel
5 out of 5 average rating, 7 reviews

Maritime Meadows – Charming Resort-Style Home!

GaryRating, 5 stars6 months ago
We thoroughly enjoyed our nearly two week stay at the Cottage Preserve. Franny was especially helpful with our questions.

Condo rentals with a pool

Top guest favorite
A serene view features a row of houses lining the water's edge, surrounded by natural greenery. The landscape includes telephone poles and nearby picnic tables, with the horizon showcasing a calm bay that reflects the soft light of the evening.
Condo in Wells
4.96 out of 5 average rating, 27 reviews

Cozy Beach Condo in Wells - Hot Tub & Pool!

BrianRating, 5 stars1 week ago
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.
Superhost
A spacious living area features a large red sectional sofa adorned with star decor. Natural light fills the room through multiple windows. A small white coffee table sits at the center, complemented by a decorative tray with snacks and two wine glasses.
Condo in Wells
4.5 out of 5 average rating, 6 reviews

>ONE MILE to Wells Beach< Barefoot | Beach Breeze

SharonRating, 5 stars8 months ago
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!
Guest favorite
A spacious saltwater pool area is surrounded by lounge chairs and umbrellas. The pool features a relaxing curve and clear blue water, set against a backdrop of well-maintained landscaping and neighboring buildings. The concrete deck provides ample space for sunbathing and relaxation.
Condo in Wells
4.91 out of 5 average rating, 90 reviews

Starfish Condo Wells Beach

Kay-LeeRating, 5 stars1 month ago
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 😁
Superhost
A serene outdoor area features a rectangular pool surrounded by a sun deck. Colorful lounge chairs and umbrellas are arranged around the pool, with a backdrop of lush green trees providing privacy. A pathway leads to the pool from the nearby building.
Condo in Wells
4.71 out of 5 average rating, 7 reviews

Awesome get away spot in Wells!

ManuelaRating, 5 stars6 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
An outdoor heated pool is framed by lounge chairs, providing a space for relaxation. The pool reflects the two-story building behind, with large windows visible. Umbrellas offer shade on sunny days, and well-maintained grass surrounds the pool area.
Condo in Wells
4.75 out of 5 average rating, 126 reviews

Generic Two Bedroom - Stair access only

Rose-MarieRating, 5 stars1 month ago
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.
Superhost
A clear swimming pool is framed by lounge chairs and vibrant greenery. A colorful towel featuring a flamingo and tropical designs is laid out on the poolside, providing a pop of color against the light concrete deck.
Condo in Wells
4.86 out of 5 average rating, 37 reviews

Drake's Island Beach Area Studio

EmilyRating, 5 stars7 months ago
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 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland
  6. Rentals with pools