Vacation 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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Guest favorite

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, 632 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 favorite

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.

Apartment in Cape Elizabeth

4.87 out of 5 average rating, 561 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

Guest favorite

Home in North Deering

4.96 out of 5 average rating, 134 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 favorite

The entrance sign of Ocean Park Meadows is prominently displayed, featuring wooden textures and flowing wave designs. The name 'Ocean Park Meadows' is artistically rendered in gold lettering, set against a blue background, surrounded by greenery and natural landscaping.

Condo in Old Orchard Beach

5 out of 5 average rating, 27 reviews

Lovely 2 bedroom condo, 400 ft from sandy beach

Enjoy a get away at this amazing 2 bedroom, full bathroom, condo located in one of Old Orchards Beach most popular condo communities. Relaxing 2 min. walk will bring you to miles of sandy beach. Modern kitchen with granite counter tops, private deck over looking salt water marsh. Take advantage of the many amenities with complimentary WIFI internet, air conditioning, washer/dryer, dishwasher, gas grill, linens furnished. Offers pool, pickleball, sauna, clubhouse, free parking, sorry no pets.

Guest favorite

A glass-enclosed sunroom features a heated indoor fitness pool beside a hot tub. Natural light floods the space, highlighting wooden decking and various potted plants. The view extends to a grassy outdoor area visible through transparent walls.

Home in Scarborough

4.89 out of 5 average rating, 18 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 favorite

The exterior of a charming three-story building is visible, adorned with a warm stucco finish. A seasonal pool in the foreground reflects the structure. Various patio seating options and an umbrella area create an inviting outdoor space, complemented by lush greenery in the surrounding garden.

Apartment in Rosemont

4.98 out of 5 average rating, 258 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.

Top guest favorite

Place to stay in Shapleigh

5 out of 5 average rating, 80 reviews

Historic Schoolhouse c1866 / Pets OK / Hot tub

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

Guest favorite

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, 153 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 favorite

A refreshing seasonal pool displays sparkling blue water, surrounded by a spacious deck and lawns. A colorful striped pool float rests on the surface, while the historic Chapman House is visible in the background, framed by tall trees and sunlight filtering through.

Guesthouse in Rosemont

4.96 out of 5 average rating, 524 reviews

Romantic Bungalow w/ Pool, Hot Tub & Parking

The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Guest favorite

A swimming pool is framed by a concrete deck, with lounge chairs positioned nearby. Colorful chairs are set along the fence, which provides a boundary. A serene evening sky with soft hues enhances the tranquil setting.

Guest suite in Standish

4.92 out of 5 average rating, 108 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.

Superhost

An aerial view captures the vibrant beach town, with the sandy shore, pier, and surrounding park visible. The second image shows the pool area, featuring a bright inflatable unicorn and a large pink float in clear water. A cozy room is displayed, featuring two full-size beds with white linens and light-colored accents.

Condo in Old Orchard Beach

5 out of 5 average rating, 3 reviews

Steps to Beach, Pier, Park | Condo with Pool • 3

Welcome to Sunset Suites, your ideal getaway in the heart of Old Orchard Beach! Each updated 1-bedroom suite features a kitchenette with a sink, fridge, and stove, a private bathroom with a shower, 2 full size beds. Enjoy our on-site pool or take advantage of the fantastic location: adjacent to a park with tennis courts, and just a short stroll to Playland Adventures, the famous pier, and the beach. Experience your perfect home away from home!

Superhost

A clear blue swimming pool is featured at the center, surrounded by lounge chairs on the sunbaked concrete deck. A fenced area and trees in the background provide a natural setting, with additional homes visible nearby, creating a welcoming community atmosphere.

Home in Old Orchard Beach

5 out of 5 average rating, 4 reviews

Family Fun with Community Pool

My 3rd property in this beautiful community. Please check my reviews on Faith Lane which has been listed for 3 years. Back patio will have 2 tables and grill for outdoor dining and fun. Newly built 3 bedroom in a beautiful community with a pool. 5 minute drive to the beach and great spot for family vacations. The beach trolley stop at Elmwood and Marcotte Motors Motel can take you right to the beach.