Holiday rentals with a pool in South Portland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in South Portland

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

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Superhost

Home in Kennebunk

4.82 out of 5 average rating, 39 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. Enjoy the hot tub and the 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!

Top guest favourite

Home in Ogunquit

5 out of 5 average rating, 55 reviews

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Welcome to your Ogunquit Oasis, a luxurious 5-bedroom beach house located on the edge of Ogunquit Village. Walk to the beach, restaurants, Perkins Cove, Marginal Way & everything in Ogunquit! The house features a heated pool that reaches 104 degrees, ideal for all seasons. Built in 2014, the house includes central air, three Ultra HD TVs, and wireless speakers. The dining table seats 10, with an outdoor living room, grill, & gas firepit. Each spacious bedroom offers plush bedding & ceiling fans.

Guest favourite

Home in Kennebunk

4.83 out of 5 average rating, 143 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.

Guest favourite

Cabin in Wakefield

4.93 out of 5 average rating, 42 reviews

Lakeside cabin in the woods

Relax with the whole family at this peaceful four-season cabin. Access to private association beach and public boat launch. Open floor plan with cathedral ceilings and spiral stairs to second floor or full basement. Enjoy dinner inside the private fenced yard beside the saltwater pool (mid May-Oct) and s’mores at the fire pit beside the screened pool house. Explore your own private nature trails on the property’s 10 acres with educational signs or sip coffee in the morning as the deer graze.

Guest favourite

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.

Superhost

Cottage in Wells

4.89 out of 5 average rating, 57 reviews

Cozy beach cottage with pool & hot tub

Relax and enjoy the beauty of Wells Beach and surrounding area in our cozy cottage. We are part of a community complete with a heated pool, hot tub, play ground, & more! Wells Beach is less than 2 miles away. Our cottage is most comfortable for 2-3 people. *For sanitary reasons, we do not provide blankets. We ask that you please bring your own. Sheets and pillowcases will be left on the full bed and additional linens for the other beds can be rented from the main office

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.

Guest favourite

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.

Top guest favourite

Home in Old Orchard Beach

5 out of 5 average rating, 106 reviews

OOB Oasis - 5BR private Retreat w/ Pool

Welcome to our stunning home, and your private oasis in Old Orchard Beach! Inside, this custom-built home features 3 suites (each with its own private bathroom), a gourmet kitchen w/ high-end appliances, a sprawling open floor plan, and ample parking for large groups. Outside, you'll find a large fenced backyard, deck with BBQ grill, and in-ground pool perfect for cooling off on hot summer days.

Guest favourite

Home in Wells

5 out of 5 average rating, 48 reviews

2BR, Sea & Relax w/ Wells Reserve View

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 Wells National Reserve. Mike's Clam Shack, Congdon's, The Steakhouse, Fish Camp and more all within walking distance. 1.3 Miles to Wells Beach. Less than 4 miles (6 min drive!) to Ogunquit Beach.

Guest favourite

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.