Holiday rentals with a pool in Old Orchard Beach

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Top-rated rentals with a pool in Old Orchard Beach

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Top guest favourite
The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.
Loft in Falmouth
4.95 out of 5 average rating, 652 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
An aerial view captures the condo community and its proximity to Old Orchard Beach. The clear blue ocean stretches in the background, with sandy shores visible. The surrounding area includes recreational facilities and parking, illustrating the convenient access to nearby attractions.
Apartment in Old Orchard Beach
5 out of 5 average rating, 12 reviews

Condo in Old Orchard Beach

Your Perfect Old Orchard Beach Getaway This beautiful condo (Unit 19), is the ideal retreat to experience the best of Old Orchard Beach! This family friendly property offers the perfect balance of comfort and convenience. Just a short walk to the pier, downtown, and the beach! Includes: - 2 bedrooms, each w/fan and balcony - Pool - Washer & Drier - 2 Smart TVs - Microwave - 4 burner cooktop - Kitchen Table - Sofa - Refrigerator - Toaster - Keurig - Parking for 1 vehicle (paid parking close by)

Guest favourite
A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.
Flat in Cape Elizabeth
4.88 out of 5 average rating, 576 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
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in North Deering
4.96 out of 5 average rating, 147 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

Top guest favourite
A living room displays a gray tufted sofa adorned with decorative pillows and a green accent pillow. A round wooden tray holds two white candles on a leather ottoman. Two elegant lamps provide soft lighting, complemented by large windows draped with sheer curtains.
Flat in Rosemont
4.97 out of 5 average rating, 450 reviews

Apt in Victorian Mansion w/ Hot Tub, Pool, Parking

Mixing contemporary styling with old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our pool or relax by the fire pit, our half-acre yard offers a tranquil space for all. The apartment has a chef's kitchen, dining, and living room with gas fireplace. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

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Home in Arundel
5 out of 5 average rating, 3 reviews

Designers Dream Home with Pool!

Discover this brand-new, beautifully appointed 2-bedroom home nestled within a secure, private community surrounded by 200 acres of preserved natural beauty. Enjoy full access to outdoor heated pools, a clubhouse featuring a game room (with ping pong, foosball, shuffleboard, and a poker room), and a fully equipped fitness center to keep you on routine. Mingle with fellow guests at the clubhouse or relax in your peaceful, private backyard, and enjoy the perfect balance of activity and serenity.

Top guest favourite
Flat in Rosemont
4.99 out of 5 average rating, 267 reviews

Maine Hacienda w/hot tub & 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
A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.
Cottage in Wells
4.94 out of 5 average rating, 162 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 favourite
A spacious living area features comfortable seating arranged around a central black coffee table. A large flat-screen TV is mounted on a built-in unit, while the room is illuminated by natural light from a doorway and recessed lighting. Decorative items enhance the neutral decor.
Home in Old Orchard Beach
4.97 out of 5 average rating, 123 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
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish
4.92 out of 5 average rating, 115 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.

Top guest favourite
A bright sitting room features large windows that invite natural light and offer views of the harbor. A round table with two chairs occupies the space, alongside a built-in seating area with cushions. A door leads to an outdoor deck, enhancing indoor-outdoor connectivity.
Guest suite in West End
4.99 out of 5 average rating, 350 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. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

Guest favourite
A serene community pool is surrounded by a spacious deck with lounge chairs for relaxation. Tall trees in the background provide a natural setting, while neighboring homes are visible, enhancing the sense of community.
Home in Old Orchard Beach
4.96 out of 5 average rating, 106 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 at Elmwood and Marcotte Motors Motel can take you right to the beach.

Popular amenities for Old Orchard Beach rentals with a pool

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

  • Total rentals

    160 properties

  • Nightly prices starting at

    £37 before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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