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Vacation rentals with a pool in Cumberland County

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Top-rated rentals with a pool in Cumberland County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Guest suite in Portland
Sunny West End Guest Suite with Harbor Views
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. This garden oasis with stone walls and salt water pool (open seasonally) is walking distance to downtown. (Portland City Permit: 20185360-ST) Your safety is important to us! We are following strict guidelines for sanitizing all linens, towels, furniture, objects and surfaces. Airbnb has an incredibly thorough and helpful protocol! All doorknobs, light switches and hand-touched surfaces will also be alcohol sanitized for your arrival! Here is a link to the protocol we are following: https://www.airbnb.com/resources/hosting-homes/a/airbnbs-5-step-cleaning-process-explained-187. Please let us know if you have any questions! This guest suite is a private, two-floor space attached to our house. It has its own front and back entrances and is separated by locked doors upstairs and downstairs from the main part of the house. The suite is light and sunny and a wonderful place to rest. The downstairs sitting room has a table for two and built in seating for relaxing and enjoying the water views or watching tv. The bedroom and bathroom are upstairs with lovely views. You will given your unique code for the guest suite door which enables you to come and go on your own timing. Parking is always available in front of the house or within a block. Please note that parking is prohibited on our side of the street on Monday nights through Tuesday mornings the 2nd and 4th Monday of the month. You can park on the opposite side of the street. The guest suite is attached to our house, but with its own front and back entrances. The day before you arrive we will send you instructions about your arrival. There is a key code so you can enter on your own. We may see each other on the back deck or in the yard at the pool. We have two dogs and you might see them in the yard and also coming up the stairs to our back deck door. We are right next door if you need anything or have any questions, and are also very conscious of your privacy. Please feel free to reach out if you need anything. We love Portland! Just let us know if you would like advice on local hikes, beaches, entertainment or great food. Portland has incredible restaurants! Most within walking distance from the house. The house is in the historic West End neighborhood overlooking the working harbor of the Fore River. Within walking distance are Portland's Old Port and Arts Districts, as well as the Saturday Farmers' Market in Deering Oaks Park. Parking is very easy on the street in front of the house. You can drive to local spots like the beautiful lighthouse at Fort Williams in Cape Elizabeth or the beaches in Scarborough, but you can walk to downtown Portland in 15-20 minutes. It's great to visit Portland on foot. You can walk Danforth Street all the way down to the Old Port shopping area. Here are directions for a nice walk to the Old Port: Turn right on Danforth when leaving the house. Take your first left on Emery Street. At the four way stop, turn right on Spring Street. Take Spring Street for just over a mile. After passing Temple Street, take your first right onto Exchange Street. This is the heart of the Old Port. Have fun!! Please Note: All Guests agree to indemnify and hold the Property Owners harmless from any liability for personal injury or property damage sustained by Guest or parties invited onto the property by Guest.
Apr 21 – 26
$142 per night
4.99 out of 5 average rating, 260 reviews
Guest favorite
Loft in Falmouth
Loft Apartment on Tree-Lined Street in Falmouth
Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.
May 28 – Jun 4
$275 per night
4.95 out of 5 average rating, 531 reviews
Superhost
Tiny home in Harrison
MILLION$ views, HOT TUB, Crooked RIVER, 14 acres
Pets Welcome. Hot tub with a EPIC view. Escape to complete privacy on 14 acres of stunning riverfront property on the Crooked River. This A-frame cabin offers plenty of outdoor activities, a pond, riverfront access, and trails for picking berries. Relax by the river, go camping, or spot wildlife from the front porch or hot tub. The home is clean, modern, and tidy with a new bathroom and furniture. It also has air conditioning. Don't miss out on this unique getaway opportunity.
Aug 14 – 21
$460 per night
4.9 out of 5 average rating, 277 reviews

Popular amenities for Cumberland County rentals with a pool

House rentals with a pool

Guest favorite
Home in Bridgton
Moose Pond Mountain Escape
May 28 – Jun 4
$167 per night
4.89 out of 5 average rating, 152 reviews
Superhost
Home in Yarmouth
The Royal River Retreat
Mar 14 – 21
$585 per night
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Gorham
Large Private Maine Home with Pool in Gorham
Dec 22 – 29
$520 per night
4.83 out of 5 average rating, 23 reviews
Guest favorite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Apr 16 – 23
$324 per night
4.94 out of 5 average rating, 67 reviews
Guest favorite
Home in Old Orchard Beach
OOB Oasis - 5BR private Retreat w/ Pool
May 7 – 14
$803 per night
5.0 out of 5 average rating, 44 reviews
Guest favorite
Home in Old Orchard Beach
Our Beach House Getaway
Oct 12 – 19
$575 per night
5.0 out of 5 average rating, 26 reviews
Guest favorite
Home in Standish
6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK
May 5 – 12
$540 per night
4.95 out of 5 average rating, 40 reviews
Guest favorite
Home in Old Orchard Beach
The Happy Cottage
May 18 – 25
$196 per night
5.0 out of 5 average rating, 42 reviews
Guest favorite
Home in Scarborough
Private Cape with Spa minutes from beach/Portland
Aug 19 – 24
$400 per night
4.95 out of 5 average rating, 62 reviews
Guest favorite
Home in Old Orchard Beach
Faith Lane with community pool
Jul 31 – Aug 7
$556 per night
4.97 out of 5 average rating, 60 reviews
Guest favorite
Home in Portland
There's No Place Like Home
Jul 22 – 29
$406 per night
4.82 out of 5 average rating, 98 reviews
Guest favorite
Home in Bridgton
3 mins to Pleasant Mt/Moose Pond w/hot tub & sauna
Feb 5 – 12
$390 per night
4.92 out of 5 average rating, 38 reviews

Condo rentals with a pool

Guest favorite
Condo in Old Orchard Beach
Gorgeous OceanView condo and Grand Victorian - #301
Oct 4 – 11
$345 per night
4.81 out of 5 average rating, 32 reviews
Guest favorite
Condo in Old Orchard Beach
CHowder Ocean Oasis @ Old Orchard Beach
Jul 13 – 20
$285 per night
4.84 out of 5 average rating, 19 reviews
Superhost
Condo in Old Orchard Beach
30 second walk to Beach- Pool-Outdoor Shower
Jun 15 – 22
$350 per night
4.83 out of 5 average rating, 6 reviews
Guest favorite
Condo in Old Orchard Beach
Grand Victorian Ocean Rentals Oob310
Dec 11 – 18
$639 per night
4.89 out of 5 average rating, 9 reviews
Superhost
Condo in Old Orchard Beach
Ocean View Studio Beach Condo
Dec 28 – Jan 4
$50 per night
New place to stay
Guest favorite
Condo in Old Orchard Beach
Summer 24 dates available Grand Victorian Condo
Sep 21 – 28
$457 per night
4.88 out of 5 average rating, 17 reviews
Condo in Old Orchard Beach
Maine, Beach front Condo! Vacation hotspot!
May 1 – 8
$300 per night
4.81 out of 5 average rating, 32 reviews
Condo in Old Orchard Beach
Steps to the beach, Pool, 3rd Floor ocean view
Mar 26 – Apr 2
$265 per night
4.75 out of 5 average rating, 8 reviews
Condo in Old Orchard Beach
*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM
Jun 10 – 17
$649 per night
4.82 out of 5 average rating, 39 reviews
Guest favorite
Condo in Old Orchard Beach
LUXURY OCEANFRONT CONDO Best Location on the beach
May 27 – Jun 3
$268 per night
5.0 out of 5 average rating, 11 reviews
Condo in Old Orchard Beach
Great beach condo in quaint Ocean Park, ME
Dec 7 – 14
$350 per night
4.67 out of 5 average rating, 3 reviews
Guest favorite
Condo in Old Orchard Beach
Lovely 2 bedroom condo, 400 ft from sandy beach
Sep 12 – 19
$277 per night
5.0 out of 5 average rating, 18 reviews

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