Vacation rentals with a pool in Kennebunkport

Find and book unique homes with a pool on Airbnb

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Popular amenities for Kennebunkport rentals with a pool

House rentals with a pool

Guest favourite
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.
Superhost
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 favourite
Home in Old Orchard Beach
4.97 out of 5 average rating, 33 reviews

Upscale OOB Beach House | Seasonal Heated Pool

CaseyRating, 5 stars1 month ago
We had a great time! Great location and very clean space!
Top guest favourite
Home in Biddeford
5 out of 5 average rating, 27 reviews

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

AshleyRating, 5 stars6 months ago
Thank you for allowing us to stay at your beautiful home. The photos did it no justice! I can’t wait to be back, we will be stay here again.
Top guest favourite
Home in Fryeburg
4.97 out of 5 average rating, 30 reviews

The Lodge at Hidden Pines

JordannaRating, 5 stars1 month 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 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 favourite
Home in Portland
4.96 out of 5 average rating, 121 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Kathleen AudreyRating, 5 stars1 week ago
My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!
Superhost
Home in Conway
4.63 out of 5 average rating, 16 reviews

80-2 Locust Lane

KevinRating, 5 stars12 months ago
Our Family get together was a major success! Ned was friendly and kind and made the check in process as easy as possible. The entire home was beautiful and looked exactly like the pictures and the amenities were exactly what we wanted from the pool table to the Hot Tub it was all amazing, and we had more than enough room to accommodate everyone and made so many memories. We will definitely be visiting again in the future.

Condo rentals with a pool

Guest favourite
Condo in Conway
4.86 out of 5 average rating, 58 reviews

Cozy Mountain Condo 2bd/2bath in North Conway

SkylarRating, 5 stars2 months ago
This was the perfect spot for a couples trip. Right next to all of the activities we had planned, close to Zebs as well as the outlets. I will be booking with them in the future. They were very friendly and the check in was easy.
Guest favourite
Condo in Wells
4.84 out of 5 average rating, 178 reviews

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

EverRating, 5 stars1 week ago
100 percent recommended!!
Guest favourite
Condo in Conway
4.98 out of 5 average rating, 61 reviews

True Upscale Ski In & Out Condo with Pool & Hot Tu

BrianRating, 5 stars3 weeks ago
Condo was as advertised. Clean and great amenities. Great spot for ski weekend. Meredith was great host. We would definitely stay here again.
Guest favourite
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
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.
Top guest favourite
Condo in Conway
4.98 out of 5 average rating, 110 reviews

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

TrevorRating, 5 stars1 month ago
Jennifer's place is AMAZING! First, it's steps away from the ski lift. Not only can you make first tracks, but stopping for lunch/breaks/warm-up is super easy - ski to your door! Getting in was a breeze: pull up, get the FOB, grab a luggage rack and park in the designated spot by the door and you're done. No long walks hauling ski gear through endless parking lots. The condo is spacious, super comfortable, and great for hanging out. We had 4 adults and 4 kids (8-11) and we had plenty of room for game nights, dinners, and lounging after a long ski day. The bathrooms are big (and even a jet tub for bubble baths). And immaculately clean. Full kitchen equipped with everything you need. So great to have washer/dryer to get gear ready for the next day. And the heated pool/hot tub is a short walk, both are big and a hit with the kids and adults. And did I mention how clean the place was? The unit is on the end to give extra privacy and easy access. Six stars!
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 stars3 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!!!!
Guest favourite
Condo in Hampton Beach
4.96 out of 5 average rating, 56 reviews

Plum Pad: Luxury Condo Overlooking the Ocean

BethanyRating, 5 stars6 months ago
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

    $152 CAD before taxes and fees

  • Total number of reviews

    160 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Kennebunkport
  6. Rentals with pools