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Vacation rentals with a pool in Boothbay

Find and book unique homes with a pool on Airbnb

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Popular amenities for Boothbay 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.
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 stars2 weeks 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 stars7 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 oceanfront cottage features a large wrap-around double deck porch and multiple outdoor seating areas. The sandy beach extends directly to the base, while stairs lead up to the entrance. The inviting structure is surrounded by a relaxing atmosphere, enhanced by the presence of nearby dunes.
Home in Old Orchard Beach
4.9 out of 5 average rating, 10 reviews

Oceanfront Cottage 1

LoganRating, 5 stars1 month ago
We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!
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 stars8 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.
Superhost
An in-ground pool is framed by a spacious deck, featuring lounge chairs and seating areas. Surrounding greenery provides a sense of privacy. A light-colored exterior of the house can be seen in the background, contributing to the relaxing ambiance of the outdoor space.
Home in Rockport
4.96 out of 5 average rating, 52 reviews

Dog Friendly Midcoast Cape

SarahRating, 5 stars6 months ago
BEAUTIFUL Home!! Tons of space to relax and spread out with our family! The beds were very comfortable! We really appreciated all of the bathrooms for our group! The kitchen was huge and so handy for preparing meals! I absolutely loved the style and atmosphere of this wonderful home! We also loved being able to bring our dogs!! We had a lovely time and we would most definitely come back!!! 🥰
Guest favorite
An aerial view of a spacious backyard showcases a well-maintained heated pool surrounded by a patio area with seating. Lush greenery and trees frame the property, enhancing the outdoor space, while a shaded fire pit area and landscaped garden beds are visible.
Home in Portland
5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

DanielRating, 5 stars6 months ago
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

Condo rentals with a pool

A sparkling swimming pool is surrounded by a fence, with four white chairs arranged nearby. Sunlight reflects off the calm water, creating a serene atmosphere. The view includes a clear sky and a distant building, enhancing the outdoor environment.
Condo in Old Orchard Beach
4.78 out of 5 average rating, 9 reviews

30 second walk to Beach- Pool-Outdoor Shower

AleeshaRating, 5 stars9 months ago
place is perfect for my parents who are older and can easily get in and out of the condo. fellow people at the condo are nice and respectful.
A clear blue sky overlooks a serene swimming pool surrounded by a white picket fence. The pool area features lounge chairs and is framed by lush green grass. In the background, a two-story building with multiple windows is visible, set among trees.
Condo in Damariscotta
4.74 out of 5 average rating, 53 reviews

Beautiful Midcoast Maine Condo with inground pool

MarieRating, 5 stars7 months ago
This is the second time that we stayed at Allen's place, and we have already booked a stay for 2025. The condo is clean, tastefully decorated, and equipped with everything we needed for our stay. It is located in a great location to explore the coast, head north one day, and south the next, etc. It is quiet and secure and Allen and Cheryl are quick to answer questions. I can't recommend their place highly enough!!
Top guest favorite
A vibrant view captures the amusement park, featuring a large Ferris wheel and colorful attractions. The beach stretches in the background, illuminated by a soft, pastel sunset. A lively crowd gathers below, enjoying the bustling atmosphere of the town square.
Condo in Old Orchard Beach
5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars9 months ago
This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!
The community pool is surrounded by a deck featuring numerous lounge chairs and tables with umbrellas for shade. Lush greenery lines the perimeter, providing a serene backdrop, while the crystal-clear water invites relaxation.
Condo in Old Orchard Beach
4.83 out of 5 average rating, 30 reviews

Great Vacation-2 BR Condo, Beach, Amenities, Fun!

BrianRating, 5 stars44 months ago
Alice’s condo in Old Orchard Beach is exactly as advertised. It was in sparkling condition when we arrived, it’s a very short walk to the beach (when we were able to tear the kids away from the pool!), and it is the perfect distance from the center of town: close enough to walk, but far enough away to enjoy some privacy and distance from the crowds. We even managed to squeeze in a quick workout in the small gym. We would absolutely stay here again. Thank you so much, Alice!
A spacious outdoor pool is surrounded by a textured deck, featuring numerous blue lounge chairs and shaded umbrellas. Trees provide a natural backdrop, and a nearby building complements the inviting environment. Clear water sparkles under sunlight, creating a refreshing atmosphere for relaxation.
Condo in Old Orchard Beach
4.82 out of 5 average rating, 11 reviews

Family Vacation Home walking distance to Beach

LaraRating, 5 stars20 months ago
This was our second year staying at Chandra’s place during our annual week in Maine and it was, once again, terrific. Quiet, clean and within walking distance to the beach and all Ocean Park/Old Orchard attractions. When the washing machine wasn’t working, Chandra was very responsive and immediately offered to cover our costs of using the laundromat (which she did at the end of the week). We would definitely go back again next year!
An indoor pool area features clear water surrounded by spacious tiled flooring. Comfortable red loungers are positioned around the pool, with large windows offering views of the outside. Potted plants add touches of greenery, enhancing the tranquil setting.
Condo in Old Orchard Beach
4.78 out of 5 average rating, 37 reviews

Gorgeous OceanView condo and Grand Victorian - #301

JonRating, 5 stars8 months ago
Check in is super simple and quick with friendly front desk staff. The condo has an open concept kitchen/living room which allows continuous interaction with family. 2 full bathrooms were more than enough to accommodate 4 adults and 2 children. Both bedrooms were very accommodating for all of us. You will have your own parking spot the entire length of your stay, a 2nd car will have to park in a separate lot about a block away from the actual condo. Everything you could need is in walking distance unless you want to travel outside of old orchard, you won’t need to touch your car. The best part for us with young children was how close the beach was this was a MUST for us and it was perfect. Thank you for allowing us to stay in your home. We would definitely come back if you would have us again.
A panoramic view of the beach is captured from a balcony, featuring gentle waves lapping at the shore under a bright sun. The shimmering water reflects sunlight, while a sandy area stretches across the foreground, enhancing the coastal atmosphere.
Condo in Old Orchard Beach
4.67 out of 5 average rating, 3 reviews

Old Orchard Beach Oceanfront Condo w/ Pool

MartinRating, 5 stars7 months ago
Great place to enjoy the beach and the neighborhood 😃

Quick stats about vacation rentals with a pool in Boothbay

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ404 before taxes and fees

  • Total number of reviews

    130 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Lincoln County
  5. Boothbay
  6. Rentals with pools