Holiday rentals with a pool in Cumberland County

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Popular amenities for Cumberland County rentals with a pool

House rentals with a pool

Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 35 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

TrishRating, 5 stars1 week ago
we can't say enough about lovely our stay was at this beautiful house in OOB. the house is so clean and bright. its within walking distance to restaurants and stores. its right across from the heated pool. it really is such a gem!
Guest favourite
Home in Sebago
5 out of 5 average rating, 19 reviews

Treehouse Farm - Sebago

TheresaRating, 5 starstoday
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.
Guest favourite
Home in Old Orchard Beach
4.98 out of 5 average rating, 83 reviews

Faith Lane with community pool

MariaRating, 5 stars6 days ago
We had a wonderful stay- place was pristine and welcoming, looks exactly like the photos. Of course being closer to water is always great and can’t beat it for the price. Many OOB hotels leave much to be desired and are outrageously expensive for what you get. After some less than stellar experiences, to be somewhere clean, free of bugs and animals was a relief. Easy uber ride or trolley to boardwalk. Definitely would rent there again!
Guest favourite
Home in Old Orchard Beach
4.98 out of 5 average rating, 41 reviews

Upscale OOB Beach House | Seasonal Heated Pool

BonnieRating, 5 stars2 weeks ago
This was the perfect home base for exploring various parts of the Maine coast. Beds were comfy, and each room had a wall unit to make it the temperature you like. Our kids loved being upstairs in the 3 beds room and having their own space. WiFi worked great, and that was with 7 of us on it doing various things - adults working, kids streaming. Would definitely stay here again.
Top guest favourite
Home in Bridgton
5 out of 5 average rating, 19 reviews

Cozy Knights Hill Home

KellyRating, 5 stars3 months ago
We had a great stay at the house. Chris and Nadine were very responsive and helpful with information. The house is so comfortable in terms of layout and has everything you need. We enjoyed sitting by the fire and relaxing at the end of the day. Would highly recommend this home if you are staying in the area.
Superhost
Home in Old Orchard Beach
4.82 out of 5 average rating, 11 reviews

Oceanfront Cottage 1

LoganRating, 5 stars3 months ago
We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!
Top guest favourite
Home in Biddeford
4.97 out of 5 average rating, 34 reviews

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

JennaRating, 5 stars3 days ago
The house was spotless and centrally located for what we wanted to do in southern Maine. It was well stocked with quality toilet paper, napkins and Kleenex. We had plenty of towels for the hot tub and pool. It is updated and well taken care of. The hosts were extremely helpful and we didn’t see them at all, so the place felt very private. This was an amazing house and our kids had so much fun in the pool and playing corn hole on the large deck. Would recommend this house for families and couples in a heartbeat!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 20 reviews

Lovely home with hot tub and pool

ErnieRating, 5 stars4 days ago
I had a wonderful stay., they were fantastic in accommodations for me and my service dog who loved the yard. The home is beautiful and the host was very accommodating. communication was great. I look forward to staying there when I’m in that area again.

Apartment rentals with a pool

Top guest favourite
Apartment in Old Orchard Beach
5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars11 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!
Apartment in Old Orchard Beach
4.81 out of 5 average rating, 48 reviews

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

CaseyRating, 5 stars9 months ago
Located right in the middle of all the action! Perfect beach access and my kids had a blast at palace playland. Unit had everything we needed.
Apartment in Old Orchard Beach
5 out of 5 average rating, 4 reviews

Just steps to the beach

GingerRating, 5 stars10 months ago
This was exactly what we needed! What a perfect little place. It’s a 30-second walk to the beach and an easy 1.3 mile walk to the downtown area. We walked everywhere and clocked 15 miles per day between the beach stroll in the AM, scooter/jog with my kids to the arcade at 10am, and afternoon/evening walks to the nonstop carnival. The apartment has everything you need and the kitchen is so well stocked with the basics. Such a great place! Perfect for a family visit to the beach. Also, I was surprised by how clean and safe the downtown felt. Ideal for families and young kids. Thank you, Julie!
Superhost
Apartment in Old Orchard Beach

Ocean View Studio Beach Condo

MargaretRating, 5 stars30 months ago
It was such a cozy, wonderful condo with ocean sounds and breezes right from the front door. Neighbors very kind and welcoming; never felt like a stranger from the first day! Although just a studio, quite spacious and very comfortable even when my husband and child came to visit! David always responded to any questions rather about the condo, condo building, or just a good place to eat! Just a lovely all around stay! All my classmates were jealous! :)
Apartment in Old Orchard Beach
4.83 out of 5 average rating, 36 reviews

Maine, Beach front Condo! Vacation hotspot!

SydneyRating, 5 stars9 months ago
Lovely place! Fully stocked with everything you could ever need! King bed was extremely comfortable. Tammy was very friendly and responsive! Will definitely be back in the future!
Apartment in Old Orchard Beach
4.82 out of 5 average rating, 11 reviews

Family Vacation Home walking distance to Beach

LaraRating, 5 stars22 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!
Apartment in Old Orchard Beach
4.78 out of 5 average rating, 37 reviews

Gorgeous OceanView condo at Grand Victorian - #301

JonRating, 5 stars9 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.
Apartment in Old Orchard Beach
4.5 out of 5 average rating, 8 reviews

Cape Cod style 2BR Waterview | Patio | Pool

MonicaRating, 5 stars34 months ago
The townhouse complex is really nice, has a pool and it's a short walk to the beach. The space is comfortable, the balcony is nice, the kitchen is really well equipped with everything you need. We had a very relaxing stay! It's really quiet and relaxing after a beach day or exploring nearby Portland. (if you're sensitive to noise - there's train that goes by a few times a day that you'll likely hear)

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