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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Guest favourite

Loft in Falmouth

4.95 out of 5 average rating, 639 reviews

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.

Guest favourite

Apartment in Cape Elizabeth

4.87 out of 5 average rating, 568 reviews

Portland & Beach & Lighthouses! Romantic! Lovely

Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

Top Guest favourite

Home in Portland

4.96 out of 5 average rating, 138 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 and breweries. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Guest favourite

Home in Standish

4.95 out of 5 average rating, 41 reviews

Unique Church Firepit Hammock Stock Tank Pool

Holy Shiitake House a Renovated Church in Sebago Lake, Maine! Escape & discover a unique vacation rental in this stunningly renovated church, historic retro charm with modern luxuries w/a full kitchen. Pond w/outdoor entertaining, grill, firepit, ST pool, hammock, games & more. Close to snowmobile/ATV trails, hiking & skiing. One-of-a-kind property offers a truly memorable stay for families, friends, or anyone looking for a special retreat. Miles to: Sebago 4 | Portland 22 | Pleasant Mt 28

Top Guest favourite

Apartment in Portland

5 out of 5 average rating, 78 reviews

Luxe Eco Studio near Back Cove

2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

Guest favourite

Home in Scarborough

4.92 out of 5 average rating, 24 reviews

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches

Experience the luxury of your own solar-powered, eco-friendly spa getaway in Maine! Enjoy a private spa in a four-season sunroom, featuring a heated indoor fitness pool and hot tub. Boost your immune system with hydrotherapy, then step outside to a sauna and fire pit -a truly indulgent retreat. Plus, we’re just minutes from beaches, lighthouses, and Portland’s Old Port! Enjoy complimentary access to beautiful local beaches and parks with our included beach pass—yours to use during your stay!

Top Guest favourite

Apartment in Portland

4.98 out of 5 average rating, 260 reviews

Maine Hacienda w/hot tube & seasonal pool

Our renovated suite at the foot of Deering Highlands is a 10 minute drive to downtown Portland. A cozy, quiet, modern space with a maritime edge. A short walk to Woodford’s corner and Forest Ave - home to many restaurants & coffee shops. The space includes a seasonal pool and year-round hot tub. Ideal for singles, couples or couples with one or two small children. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.

Guest favourite

Cottage in Wells

4.94 out of 5 average rating, 158 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.

Top Guest favourite

Home in Old Orchard Beach

4.97 out of 5 average rating, 115 reviews

OOB Oasis - Spacious 5BR private Retreat w/ Pool

Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built retreat offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, and sparkling in-ground pool—perfect for summer fun, fall gatherings, or simply relaxing after a day at the beach.

Guest favourite

Home in Portland

4.83 out of 5 average rating, 115 reviews

There's No Place Like Home

Our home is filled with cozy spaces to relax and unwind. From the outside deck and pool to the quaint private bedrooms! This family friendly BnB provides a kitchen, dining room and two living areas for a vacation haven . This home has the feel of a true BnB, yet the entire space is dedicated to our guests. We are on site in our in-law quarters, so are close at hand for questions and help if needed. Our home is located in a convenient, quiet and safe neighborhood with off street parking.

Top Guest favourite

Apartment in Portland

4.99 out of 5 average rating, 308 reviews

Tower Suite w/ Hot Tub, W/D, Pool & Parking

This newly renovated, gorgeous, spacious suite, located on the 3rd floor of our 1865 mansion, is just 10 mins to downtown and the airport. Relax by the firepit or soak in our hot tub and enjoy our gardens. We are owner-operated. The suite includes a newly renovated bath with rain shower and radiant floor heating; W/D; lounge and kitchenette w/ work table; and a large bedroom. Our half-acre yard provides ample space for privacy. Level 2 EV station is available #allarewelcome

Guest favourite

Guest suite in Standish

4.92 out of 5 average rating, 110 reviews

Steep Falls Escape, river & falls just steps away

Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.