
Holiday rentals with a pool in Boothbay Harbor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Boothbay Harbor
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Boothbay Harbor rentals with a pool
House rentals with a pool

Treehouse Farm - Sebago
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.

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

Oceanfront Cottage 1
We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!

2BR, Sea & Relax w/ Wells Reserve View
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.

House in the woods
Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

The Boathouse at Spruce Harbor
My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.

There'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!

Spectacular 3 Bed Resort Cottage
Beautiful home in a quiet, family-friendly community. We loved being able to walk up to the pool and play in the game room in the main clubhouse area. The house is a short drive to downtown Kennebunkport and local beaches. It is a quick 30 minute drive up to Portland. Our daughter loved sleeping in the private bedroom upstairs. The kitchen was fully stocked with appliances. The space was immaculate when we arrived. Steve was responsive to any needs we had during our stay. A great find!
Apartment rentals with a pool

*King Bed* Slope Side Condo at Sunday River
A very quick, 30 second walk to where you can strap on your skis or board, and ski to the nearest lift. This airbnb provides a true ski in/out experience. King bed was very comfortable. Huge TV. Lots of restaurants nearby. A perfect set up for a couple or individual.

Cozy Beach Condo in Wells - Hot Tub & Pool!
Thank you for a great stay, Kathleen! My husband and I were celebrating our anniversary and both of our birthdays that week and needed a little get away. This was perfect for us. I wish the weather was better, but you can’t do anything about that. We ate great food, went to a movie, shopped, went to the Nubble lighthouse and more. We would definitely use Kathleen again. She also made arrangements to have my favorite hoodie sent back to me as I mistakenly left it on the back of the door. Great host and super cute place!

Slopeside Sunday River Condo Brookside 2A210
Great place to stay with an awesome view of white heat!

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

6 miles from Sunday River with heated outdoor pool
Easy quick getaway for ski/snowboard trip

Starfish Condo Wells Beach
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

Generic Two Bedroom - Stair access only
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.

Relaxing Beachside Condo with Pool at Wells Beach
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.
Quick stats about holiday rentals with a pool in Boothbay Harbor
Total rentals
40 properties
Nightly prices starting at
₹9,520 before taxes and fees
Total number of reviews
60 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Sebago Lake
- Scarborough Beach
- Popham Beach State Park
- Surfside Beach
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Dunegrass Golf Club
- Wolfe's Neck Woods State Park
- Freddy Beach
- Crescent Beach State Park
- Portland Museum of Art
- Maine Maritime Museum
- Prouts Neck Country Club
- Bradbury Mountain State Park