Some info has been automatically translated. Show original language

Holiday rentals with a pool in Cumberland

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Cumberland rentals with a pool

House rentals with a pool

Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 36 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

EliseRating, 5 stars1 day ago
Clean , comfortable...home away from home...would definitely rebook if I revisit Old Orchard Beach Elisa
Guest favourite
Home in Old Orchard Beach
4.98 out of 5 average rating, 84 reviews

Faith Lane with community pool

MariaRating, 5 stars1 week 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!
Superhost
Home in Bethel
4.9 out of 5 average rating, 10 reviews

Pleasant River 3 bed | 2 bath, Pool, Hot Tub

WilliamRating, 5 stars3 months ago
Josh's place was great. close to our activities, not far from restaurants. josh was very quick to respond and remedy the only issue we had, which was with the hot tub. the only thing we didn't have that I personally wish there was, was a broom. the place was clean but I hate feeling dirt on my feet inside, so I bought a broom, but that was my decision. great place, thanks Josh
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!
Guest favourite
Home in Bridgton
4.89 out of 5 average rating, 9 reviews

Peaceful Retreat

CarolRating, 5 stars4 months ago
Aimee’s place was amazing! Absolutely gorgeous inside and out. So much attention to every detail. Aimee was quick to respond with any questions I had. The games provided great entertainment for the kids during a snowy day. I highly recommend. We can’t wait to come back.
Guest favourite
Home in Wells
5 out of 5 average rating, 53 reviews

2BR, Sea & Relax w/ Wells Reserve View

KatherineRating, 5 stars5 days ago
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.
Guest favourite
Home in Arundel
5 out of 5 average rating, 9 reviews

Maritime Meadows – Charming Resort-Style Home!

JaneRating, 5 stars3 weeks ago
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.
Superhost
Home in Arundel
5 out of 5 average rating, 3 reviews

Spectacular 3 Bed Resort Cottage

RebeccaRating, 5 stars10 months ago
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!

Condo rentals with a pool

Guest favourite
Condo in Ogunquit
4.98 out of 5 average rating, 46 reviews

Lovely Seaglass Studio, Pool, Walk to Everything!

FaithRating, 5 stars5 days ago
Denise is an outstanding host! We couldn't believe that the kitchen was FULLY stocked! from the coffee keurig, to the teaspoons and everything one would need to cook dinner or breakfast or both. We were super impressed with the quality of kitchen items and how clean everything was. Even the bathroom was stocked with the "little things" like individual make up remover packs which I was most thankful for as I had forgotten mine! The linens were beautiful and there were 3 choices of pillows for the bed! We loved that she also had clear instructions regarding towels, checking out and the use of the keyless entry. The decor is warm and welcoming...very inviting. We loved that we could walk to everything in Ogunquit and Perkins Cove. Our stay in Maine was just wonderful and we would definitely book with Denise again.
Guest favourite
Condo in Wells
4.85 out of 5 average rating, 187 reviews

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

SusanRating, 5 stars2 weeks ago
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
Guest favourite
Condo in Wells
4.91 out of 5 average rating, 92 reviews

Starfish Condo Wells Beach

WendyRating, 5 stars1 month ago
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
Guest favourite
Condo in Wells
4.95 out of 5 average rating, 102 reviews

Relaxing Beachside Condo with Pool at Wells Beach

MaryRating, 5 stars1 month ago
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.
Superhost
Condo in Wells
4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars4 weeks ago
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.
Top Guest favourite
Condo in Conway
4.98 out of 5 average rating, 110 reviews

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

TrevorRating, 5 stars3 months ago
Jennifer's place is AMAZING! First, it's steps away from the ski lift. Not only can you make first tracks, but stopping for lunch/breaks/warm-up is super easy - ski to your door! Getting in was a breeze: pull up, get the FOB, grab a luggage rack and park in the designated spot by the door and you're done. No long walks hauling ski gear through endless parking lots. The condo is spacious, super comfortable, and great for hanging out. We had 4 adults and 4 kids (8-11) and we had plenty of room for game nights, dinners, and lounging after a long ski day. The bathrooms are big (and even a jet tub for bubble baths). And immaculately clean. Full kitchen equipped with everything you need. So great to have washer/dryer to get gear ready for the next day. And the heated pool/hot tub is a short walk, both are big and a hit with the kids and adults. And did I mention how clean the place was? The unit is on the end to give extra privacy and easy access. Six stars!
Top Guest favourite
Condo in Conway
4.96 out of 5 average rating, 111 reviews

Cozy, clean, 2nd floor condo in Conway, NH!

RachelRating, 5 stars5 months ago
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!
Guest favourite
Condo in Conway
4.92 out of 5 average rating, 122 reviews

Cozy Family Retreat with Saco River Access

JeanineRating, 5 stars4 months ago
Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.

Quick stats about holiday rentals with a pool in Cumberland

  • Total rentals

    20 properties

  • Nightly prices starting at

    $67 NZD before taxes and fees

  • Total number of reviews

    320 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore