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Vacation rentals with a pool in Old Orchard Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Old Orchard Beach

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.
Mar 10 – 17
$121 per night
4.99 out of 5 average rating, 260 reviews
Guest favorite
Cottage in Wells
Cozy Cottage with Ocean Views, Wells Maine
Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.
Dec 26 – Jan 2
$189 per night
4.93 out of 5 average rating, 135 reviews
Guest favorite
Cottage in York
Tiny house living close to Ogunquit center!
The cottage was completely remodeled in spring of 2018. It is one of 21 cottages built in 1920. The back of the cottage is a rolling meadow and woods. It feels secluded, yet you are only a mile from all the wonderful happenings in Downtown Ogunquit, Perkins Cove & Ogunquit beach. Come enjoy the beach, shopping and amazing restaurants. Check out the Nubble Lighthouse, shop the outlets in Kittery or walk around Portsmouth NH. This tiny cabin is convenient to so much. Come rejuvenate!
Aug 5 – 12
$175 per night
4.98 out of 5 average rating, 118 reviews

Popular amenities for Old Orchard Beach rentals with a pool

House rentals with a pool

Guest favorite
Home in Kennebunk
Kennebunk/Kennebunkport Beach House w/Pool!
Sep 24 – Oct 1
$905 per night
4.8 out of 5 average rating, 110 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 Old Orchard Beach
OOB Oasis - 5BR private Retreat w/ Pool
Feb 4 – 11
$494 per night
5.0 out of 5 average rating, 44 reviews
Guest favorite
Home in Old Orchard Beach
Our Beach House Getaway
Mar 30 – Apr 6
$475 per night
5.0 out of 5 average rating, 26 reviews
Guest favorite
Home in Wells
Cottage in Wells Maine
Sep 28 – Oct 5
$109 per night
4.9 out of 5 average rating, 10 reviews
Superhost
Home in Yarmouth
The Royal River Retreat
Mar 3 – 10
$555 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Old Orchard Beach
Faith Lane with community pool
Aug 25 – Sep 1
$556 per night
4.97 out of 5 average rating, 60 reviews
Guest favorite
Home in Wells
2BR, Sea & Relax w/ Wells Reserve View
May 9 – 16
$222 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Home in Wells
Summertime Oasis with Inground Pool!
Oct 28 – Nov 4
$372 per night
4.93 out of 5 average rating, 15 reviews
Guest favorite
Home in Scarborough
Private Cape with Spa minutes from beach/Portland
Aug 18 – 25
$400 per night
4.95 out of 5 average rating, 62 reviews
Guest favorite
Home in Arundel
Gorgeous Home Near Kennebunkport - Heated Pool!
Sep 7 – 14
$450 per night
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Ogunquit
Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
Nov 9 – 16
$745 per night
5.0 out of 5 average rating, 27 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 Wells
Drake's Island Beach Area Studio
Oct 2 – 9
$119 per night
4.86 out of 5 average rating, 28 reviews
Guest favorite
Condo in Wells
Newly Renovated Coastal Condo Steps To Wells Beach
May 25 – Jun 1
$246 per night
4.95 out of 5 average rating, 80 reviews
Guest favorite
Condo in Old Orchard Beach
Grand Victorian Ocean Rentals Oob310
Dec 19 – 26
$639 per night
4.89 out of 5 average rating, 9 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
Superhost
Condo in York
Little Nubble Nook - Beach Condo
May 12 – 19
$185 per night
4.81 out of 5 average rating, 37 reviews
Guest favorite
Condo in Ogunquit
Lovely Studio, Pool, Walk to Everything, .5-town!
Jun 14 – 21
$168 per night
5.0 out of 5 average rating, 22 reviews
Guest favorite
Condo in Wells
Starfish Condo Wells Beach
Oct 5 – 12
$275 per night
4.88 out of 5 average rating, 67 reviews
Guest favorite
Condo in York
Cozy One bedroom condo near the beach with pool.
May 23 – 30
$210 per night
5.0 out of 5 average rating, 9 reviews
Superhost
Condo in Wells
Quaint Condo at Nautical Mile Resort - 1 BR
Nov 11 – 18
$209 per night
4.53 out of 5 average rating, 15 reviews
Superhost
Condo in Old Orchard Beach
Ocean View Studio Beach Condo
Dec 28 – Jan 4
$50 per night
New place to stay

Quick stats about vacation rentals with a pool in Old Orchard Beach

Total rentals

110 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

80 properties are a good fit for families

Total number of reviews

1.7K reviews

Nightly prices starting at

$50 before taxes and fees

Destinations to explore