
Vacation 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.
Vacation rentals for every style
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Popular amenities for Boothbay Harbor rentals with a pool
House rentals with a pool

Upscale OOB Beach House | Seasonal Heated Pool
Jason was a fantastic host—responsive, helpful, and easy to communicate with. Although we encountered a few minor issues during our stay, he responded immediately and went above and beyond to ensure everything was resolved quickly. The space itself was absolutely beautiful and made for a wonderful stay. I would highly recommend this place to anyone and hope to return in the future!

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!

Luxe Liberty: Getaway with Heated Indoor Pool!
What a wonderful experience! Rebecca was an absolutely outstanding host, always quick to respond and went above and beyond to ensure we had everything we needed. My family and I had such a peaceful stay. The home and location were incredibly tranquil, perfect for a relaxing getaway. The house and property were absolutely beautiful, and we loved sipping our morning coffee on the amazing balconies with the breathtaking views. There is so much space, and every room in the house is well thought out, functional, and cozy. The pool is even better than we hoped, so big and clean and in immaculate condition. We spent most of our time swimming and relaxing by the pool. We also enjoyed playing pool and having so many rooms to gather in with the comfort of plenty of new comfy furniture. Highly recommend for anyone looking to unwind for a vacation away from all the noise and chaos of daily life. Every single area was as described in the listing and better. Thank you for an unforgettable stay!

Coastal Retreat with Pool and Cheerful Vibes
We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.

Lovely home with hot tub and pool
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!

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

Maritime Meadows – Charming Resort-Style Home!
A beautiful home in a quiet neighborhood with everything you could need. Located a short distance from the beaches, towns, shopping and restaurants. We were here the last week of May when the crowds were not too bad. The weather was perfect—60’s and 70’s. The hosts are extremely responsive. Would definitely stay here again.

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!
Condo rentals with a pool

Cozy Beach Condo in Wells - Hot Tub & Pool!
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!!!

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

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

Pretty Boutique Studio, Pools, Walk to Everything!
Perfect for an extended weekend getaway! The condo was super clean and exactly as pictured! Hoping to stay here again in the future!

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

Coastal 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.

Slope Side | Ground floor | Hot Tub, Pool, Sauna
Will was a great host before and during our stay. He communicated well with me ahead of time with simple and easy to follow directions to (and instructions for) his place. Will’s condo was perfect for our family of four (children aged 9 and 3). We came up for Spring skiing and enjoyed the annual end of season Pond Skim and festivities in South Ridge which was easy walking/skiing distance from his place. It was great to be able to ski home for lunch and to have a break in the middle of the day. The grounds at Fall Line were awesome as well: our kids loved the common room, games, the pool, and the snow out the back door where they played on a sled. Very comfortable, clean and perfect spot for our first, but not last, visit to Sunday River. Thanks Will.

Seaside Condo w/stunning views, 2 Queen sized beds
We really enjoyed our stay, despite the weather. The accommodation was clean and very comfortable, especially the beds. Evelyn was very attentive to our needs, and very friendly and helpful. We would recommend it as a nice place to stay, and Evelyn as a great host.
Quick stats about vacation rentals with a pool in Boothbay Harbor
Total rentals
40 properties
Nightly prices starting at
$110 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
- Surfside Beach
- Popham Beach State Park
- Fox Ridge Golf Club
- Pemaquid Beach
- Brunswick Golf Club
- East End Beach
- Belgrade Lakes Golf Club
- Samoset Resort
- Palace Playland
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Ferry Beach
- Freddy Beach
- Dunegrass Golf Club
- Funtown Splashtown USA
- Portland Country Club
- Portland Museum of Art
- Wolfe's Neck Woods State Park
- Maine Maritime Museum
- Crescent Beach State Park
- Head Beach
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