
Vacation rentals with a pool in Boothbay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Boothbay
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 rentals with a pool
House rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home
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.

Upscale OOB Beach House | Seasonal Heated Pool
Great place and an even better host! Everything was seamless and I was able to contact Jason with no issues at all!

The Happy Cottage w/Pool & Hot Tub
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.

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

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!

Our Beach House Getaway
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.

Dog Friendly Midcoast Cape
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!!! 🥰

The Hill's on Buttonwood
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

30 second walk to Beach- Pool-Outdoor Shower
Séjour très agréable au condo de Mary qui est accommodant, bien équipé et confortable. La proximité de la plage et l’accès à une piscine ont été appréciés! Ce fut un moment de vacances très agréable!

Beautiful Midcoast Maine Condo with inground pool
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!!

LUXURY OCEANFRONT CONDO Best Location on the beach
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!

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

Family Vacation Home walking distance to Beach
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!

Gorgeous OceanView condo at Grand Victorian - #301
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.

Old Orchard Beach Oceanfront Condo w/ Pool
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
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- East End Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Popham Beach State Park
- Samoset Resort
- Ferry Beach
- Cliff House Beach
- Palace Playland
- Portland Museum of Art
- Wolfe's Neck Woods State Park
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- West Shore Sandy Beach
- Funtown Splashtown USA
- Dunegrass Golf Club
- Pemaquid Point Lighthouse
- Narrow Place Beach
- Freddy Beach
- Western Beach
- Aquaboggan Water Park
- Big Beach