Vacation rentals with a pool in Portland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Portland

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

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Guest favorite

Guest suite in West End

4.99 out of 5 average rating, 307 reviews

Sunny West End Guest Suite w/Harbor Views and Pool

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.

Guest favorite

Home in Kennebunk

4.82 out of 5 average rating, 132 reviews

Kennebunk/Kennebunkport Beach House w/Pool!

Perfect home for hosting and entertaining! Private in-ground pool, 600+ sq. ft. sprawling deck, large yard, and close proximity to beaches, restaurants, and shopping. Brand new renovations throughout! Amenities and features include: Newly renovated top to bottom 2 beautiful kitchens w/ granite, stainless steel appliances In-ground pool and 600 sq. ft. wrap-around deck Spacious 2 acre yard One mile from the beach Walking distance to Kennebunk Lower Village/Kennebunkport Dock Square Pet friendly!

Superhost

Home in South Berwick

4.7 out of 5 average rating, 10 reviews

Coastal Home Heated Pool, Hot Tub, Outdoor Kitchen

Spacious Log Home in private, peaceful setting- 5mi to Ogunquit beach! Pool, hot tub, outdoor dining, full outdoor kitchen. Packed with character, this home the perfect Maine getaway. After a long day at the beach, relax by the heated, saltwater pool or take a dip in the hot tub. Grill in the outdoor kitchen & sit around the firepit table. Stars are shining and deck & pool are glowing with string lights at night! 5 bedrooms, 3.5 baths- 2 are master suites w/ ensuite baths directly off the pool.

Superhost

Home in Kennebunk

4.82 out of 5 average rating, 34 reviews

Kennebunk's Charming Beach Home

Well located, our charming cozy home is just an easy stroll, less than 1 mile away from Mother's beach. 5 minutes drive from all the shop and restaurants of Kennebunkport. There are 5 comfortable bedrooms, 4 upstairs and 1 on the main floor and 2 bathrooms. The private backyard is perfect to enjoy and feel the sea breeze. Brand new hot tub and heated pool , volley ball court, fire pit, plenty of space for parking. A great place to create memories with your friends and family! Contact us!

Guest favorite

Cottage in Wells

4.94 out of 5 average rating, 146 reviews

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.

Guest favorite

Home in Arundel

5 out of 5 average rating, 5 reviews

Cheerful 2 Bdrm Home with Pool!

Immaculate 2 bdrm condo in private gated community. Unlimited access to 2 outdoor heated pools, clubhouse with game room (ping pong, foosball, shuffleboard, poker room) and fitness center. Enjoy social gatherings with other guests at the clubhouse or dine-in at your wooded backyard setting. Nestled within a 200-acre nature preserve in a modern community that has miles of walking/biking trails. A short drive away from Portland and Kennebunkport, ME and minutes to close by beaches.

Guest favorite

Home in Scarborough

4.98 out of 5 average rating, 257 reviews

Swim spa under the starry night pool/hot tub/sauna

Dreams do come true! Stay here and experience the pleasure of your own private Solar powered and Eco friendly spa resort getaway in Maine! Experience your own private spa in a four season sunroom with a heated indoor fitness pool of 90 degrees and a hot tub at 101 degrees. Boost your immune system with hydrotherapy. With an outdoor sauna steps away, and a fire pit this is truly a treat. We are close to beaches, lighthouses and Portland's Old Port just minutes away.

Superhost

Cottage in Ogunquit

4.79 out of 5 average rating, 14 reviews

1 bedroom with pool, walk to the beach.

Walk to everything and save time and money spent on parking. This peaceful and centrally-located condo is only a half mile to town and 3/4 mile to the main beach. It is flanked by Daddy's Home Made Ice Cream and the Lobster Pound Restaurant, & breakfast options are across the street. Angelina's Ristorante and the Beachfire Grill are just a brief walk north. Ogunquit is home to one of the most beautiful beaches in the world, less than a mile away from our cottage.

Superhost

Home in Windham

4.73 out of 5 average rating, 11 reviews

Gorgeous Maine House Close to Sebago Lake

Beautiful home nestled in quiet neighborhood near Sebago Lake. This home is in a great location close to ocean, lakes & the Portland area. With 4000 sq ft there is plenty of room for 1, 2 or 3 families. There are 3 family gathering spaces & 4 bedrooms. House includes hot tub/ pool, billiards, ping-pong, & INDOOR basketball courts. Wrap-around driveway makes easy in & out for boats, snowmobiles, & nearly any trailer. (NO POOL - Nov. 1st to June 1st)

Guest favorite

Home in Portland

4.95 out of 5 average rating, 104 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular eateries, breweries, and wineries in town. This centrally located home is perfect to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. City of Portland License #: STHR-004465-2022

Guest favorite

Home in Old Orchard Beach

4.98 out of 5 average rating, 80 reviews

Faith Lane with community pool

Newly built open concept with gorgeous quartz counters and vanities. 4 spacious bedrooms so large parties will be very comfortable. Deck with gas grill, table and chairs, and kids picnic table. Community pool and only minutes drive to the beach and pier. Located in the brand new Church Street Station community. The beach trolley stop is right at the entrance to the complex so makes for an easy quick ride to the beach.

Guest favorite

Cottage in Wells

4.94 out of 5 average rating, 16 reviews

Beautifully renovated 2-bedroom cottage

Your family will be close to everything (beach, restaurants, shopping and activities) when you stay at this centrally-located cottage with gorgeous water view of the Rachel Carson Reserve. Mike's Clam Shack, Congdon's, The Steakhouse, food trucks right across the street and more all within walking distance. One Mile to Wells Beach.