Vacation rentals with a pool in Kennebunkport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kennebunkport
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Kennebunkport rentals with a pool
House rentals with a pool
Home in Old Orchard Beach
5 out of 5 average rating, 29 reviewsUpscale OOB Beach House | Seasonal Heated Pool
Great place to stay in Old Orchard Beach. The house was clean and had everything we needed. Jason was a great host as well! highly recommend staying at this cute house. I would definitely want to go back here and stay!
Home in Fryeburg
4.96 out of 5 average rating, 24 reviewsThe Lodge at Hidden Pines
Perfect Getaway! We had a fantastic stay at this Airbnb! The space was impeccably clean, beautifully decorated, and had all the amenities we needed for a comfortable stay. Eileen was incredibly welcoming and provided great local recommendations. The location was ideal - close to the Fryeburg Fair grounds and other attractions yet quite enough for a peaceful retreat. We highly recommend this place and hope to make a future trip back. Thank you for a wonderful experience!
Home in Standish
4.94 out of 5 average rating, 50 reviews6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK
Perfect place for a group or big family! Was much larger than expected, very private, and had so many cute touches and details that made our stay unforgettable. I could not recommend this place enough!
Home in Kittery
5 out of 5 average rating, 23 reviewsSummer Hill: Sweet New Englander on Maine Coast
This was the perfect place for a girl's weekend. Very close to Kittery and Portsmouth shops, great seafood restaurants and State Park beaches. We were lucky the temperature was cool, as a lot of the windows didn't have screens and were too hard to open. I assumed maybe the owners haven’t fully switched over to summer mode as it's been cold up till recently. Wonderful decor, very whimsical.
Home in Portland
4.95 out of 5 average rating, 108 reviews"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Thank you for such a beautiful, clean, extremely well stocked home. Our stay was very comfortable, with extra blankets for cozy evenings on the couch, huge dining table would easily fit 8, plenty of towels. This house had everything you would need and many extra touches. If you needed scissors, they had a pair, tape, chip clip, serving dishes, games, many streaming channels, dish soap, laundry detergent. The house was a perfect fit for our family. We initially chose the house for the location, such close proximity to everything, and once we arrived we discovered it offered so much more. We would love to stay again. Thank you
Home in Portland
4.82 out of 5 average rating, 109 reviewsThere's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!
Home in Sanford
4.93 out of 5 average rating, 28 reviewsMaine Pondfront Home Sleeps 22 - Pool & Hot Tub
This House is in a really pretty setting in Maine. The home is really large and fit our family well, as we were visiting with family and were able to all have our own spaces, and dining area has plenty of seating. Looks like they've been upgrading the property incrementally. Beautiful in the fall, probably amazing in the summer.
Home in Scarborough
4.98 out of 5 average rating, 260 reviewsSwim spa under the starry night pool/hot tub/sauna
We loved our stay! Beth left a nice welcome basket and lots of great instructions and recommendations. Would happily come back.
Condo rentals with a pool
Condo in Wells
4.96 out of 5 average rating, 24 reviewsCozy Beach Condo in Wells - Hot Tub & Pool!
Great Airbnb! We enjoyed our stay. Close to all the nearby towns. Kitchen and bathroom were well stocked and clean. Comfy bed. Kathleen is super friendly and helpful!
Condo in Wells
4.92 out of 5 average rating, 26 reviewsFamily Friendly Condo | Nautical Mile Resort #111
Hosts were very communicative any time I messaged them. Condo was clean and very comfortable.
Condo in Wells
4.84 out of 5 average rating, 170 reviewsNew Condo on the Wells/Ogunquit town-line
The condo was cozy, clean and easy to find. Christopher was very responsive and gave very clear directions about everything! We stayed in December, so the area was quiet and easy to get around. Perfect for a weekend away!
Condo in Conway
4.98 out of 5 average rating, 54 reviewsTrue Upscale Ski In & Out Condo with Pool & Hot Tu
Meredith’s Cranmore condo was exactly as described and shown! It was the perfect home base for us for our friend’s wedding weekend at Cranmore. Communication was great and she kindly let us check in early. Highly recommend staying here!
Condo in Wells
4.76 out of 5 average rating, 119 reviewsTwo Bedroom Suite Condo
This was a very nice location with friendly customer service. Easy to check in, and they made sure we had plenty of towels and toiletries. The space is cute and reminds me of staying at grandma’s beach condo. Plenty of space and everything you need for a vacation getaway. Thanks!
Condo in Conway
4.98 out of 5 average rating, 102 reviews3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
We have stayed here for 3 years running for Thanksgiving and it’s always a blast. We love being at the mountain, having snow some years, and being so close to Conway. Thanks Jennifer for the memories!!!
Condo in Conway
4.96 out of 5 average rating, 109 reviewsCozy, clean, 2nd floor condo in Conway, NH!
We were two couples and the condo was perfect. A great weekend was had in this very clean condo with a nice warm vibe. Diane was very responsive and flexible with our early check in, which was appreciated. We would definitely book this condo again if available.
Condo in Hampton Beach
4.96 out of 5 average rating, 56 reviewsPlum Pad: Luxury Condo Overlooking the Ocean
This was a lovely place to stay, very cute apartment with a killer view. Right on the beach and walkable to many activities and restaurants. Brenda was great, helpful and proactive communication very early on.
Quick stats about vacation rentals with a pool in Kennebunkport
Total rentals
20 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
300 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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