Holiday rentals with a pool in Old Orchard Beach

Condo in Old Orchard Beach

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.

5 out of 5 average rating, 18 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)

Apartment in Cape Elizabeth

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.

4.87 out of 5 average rating, 590 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

5 out of 5 average rating, 54 reviews

Our Beach House Getaway

A great find describes this newly built spacious three bedroom cape style home located in peaceful private neighborhood setting with pool and parking conveniently located close to Maine Turnpike. Our home is only 1.2 miles from downtown Old Orchard Pier, Beach, shops and attractions! Step outside and catch a ride downtown on The Old Orchard Beach Seasonal Trolley or visit nearby restaurants and ice cream shop within walking distance! Our home offers many extras for a fun filled relaxing stay!

4.96 out of 5 average rating, 154 reviews

A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.

Home in North Deering

"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 shops and restaurants. 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

5 out of 5 average rating, 37 reviews

A charming two-story white house features a covered porch with railing and a central double-door entry. Lush greenery and colorful flower beds surround the property, enhancing the welcoming appearance. Large windows invite natural light, and the roof is adorned with shingles.

Condo in Kennebunkport

Luxury Oceanview Retreat | Mins from Dock Square

Minutes to Dock Square, beaches, and local restaurants. Escape to Cape Porpoise, Kennebunkport. Sea Glass is a luxury 1BR condo with ocean views, fire pit, designer interiors, a seasonal pool & LOCATION. Relax by the fire pit, walk to shops, explore the beaches, and enjoy a coastal retreat year-round. Perfect for getaways, remote work, or a classic Maine coast vacation. Experience Maine’s winter charm, spring beauty, beautiful summer and fall foliage at SeaGlass. Permit Number: STR-0008560

5 out of 5 average rating, 6 reviews

Home in Arundel

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.

Place to stay in Shapleigh

5 out of 5 average rating, 119 reviews

Historic Schoolhouse c1866 Winter & Summer Dates

Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

4.8 out of 5 average rating, 30 reviews

*Close to Beach*POOL* *5 Star Reviews*

New, beautiful 3BR/2.5BA home is ideal for your next family summer vacation! Located 1 mile from one of Maine's most popular beaches, this light & airy house is set up perfectly for a couple with main floor master bedroom & en suite bathroom, or plenty of room for the entire family with 2 comfortable bedrooms and bathroom upstairs. Amenities include community pool, wi-fi, Smart TV, and washer/dryer. Other nearby fun attractions include beach, golf courses, local shopping & fresh seafood.

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.

4.95 out of 5 average rating, 166 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.

Tiny home in Old Orchard Beach

A custom-built home is presented in warm red siding, featuring a welcoming porch with two red chairs positioned near the entrance. Large windows provide natural light, while a picnic table is located on the front yard. The driveway is paved and spacious.

5 out of 5 average rating, 20 reviews

Brand new 2 b/r tiny home, 5 minute walk to beach

This memorable place is anything but ordinary. It is a unique and family-friendly custom built home. This home includes a W/D, AC/Heat, and internet. Built in 2025, be our first guests! 5 minute walk to 7 miles of a white sand beach, amusement park and downtown with restaurants, shopping and the pier. You'll be welcome to also enjoy the swimming pool next door at Ne're Beach Family Campground. Dedicated parking for 2 cars. additional rentals: airbnb.com/h/17stjohn airbnb.com/h/21stjohn

4.95 out of 5 average rating, 136 reviews

OOB Oasis: 5BR Home w/ Private Pool Near Beach

Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built home 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.

4.97 out of 5 average rating, 593 reviews

An exterior view of The Bungalow showcases its charming design with a well-maintained greenish-yellow facade. Two black doors provide access, while vibrant flowering plants grow nearby. A small patio set with chairs and a table is prominently positioned in front, inviting outdoor relaxation.

Guesthouse in Rosemont

Private Bungalow w/ Hot Tub, Free Parking & Pool

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

Popular amenities for Old Orchard Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming two-story home features a green-shingled exterior and a gabled roof. Large windows allow natural light to fill the interior. A white front door stands at the center, with a covered entryway. A fenced area is visible in the foreground, alongside designated parking spaces.

5 out of 5 average rating, 48 reviews

Love OOB! NEW 3 BR, 2.5 BA Home Near Beaches & Fun

4.98 out of 5 average rating, 43 reviews

A covered porch is featured with wooden flooring and white railings. Two rocking chairs are positioned beside a small round table, which has a decorative pumpkin atop it. A green chair is also visible, accompanied by a colorful pillow displaying a house design.

Home in Wells

Pool and walking distance to beaches! Amenities!

4.98 out of 5 average rating, 58 reviews

Home in Biddeford

35x18Pool| Hot Tub| Private Oasis w/ Deck | Yard

4.97 out of 5 average rating, 61 reviews

Home in Standish

Unique Church Stay • Sebago Lake • Pool • Fire Pit

4.99 out of 5 average rating, 71 reviews

An open-concept living space features a well-equipped kitchen with bar seating and a cozy seating area. Natural light floods through the sliding glass doors, leading to an outdoor area. A ceiling fan hangs above, complemented by a neutral color palette and subtle decorative accents.

Home in Wells

2BR, Sea & Relax w/ Wells Reserve View

4.91 out of 5 average rating, 11 reviews

Home in Alfred

Old Falls Retreat-4BR w Gorgeous River View & Pool

5 out of 5 average rating, 14 reviews

An aerial view captures a community pool framed by lush greenery. The pool features a sandy area with scattered lounge chairs, while vibrant trees surround the space, enhancing the natural setting. Nearby buildings and pathways suggest a welcoming atmosphere for guests.

Home in Arundel

Maritime Meadows - Charming Resort-Style Home!

4.83 out of 5 average rating, 117 reviews

A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.

Home in Deering Center

There's No Place Like Home

Condo rentals with a pool

A serene view features a row of houses lining the water's edge, surrounded by natural greenery. The landscape includes telephone poles and nearby picnic tables, with the horizon showcasing a calm bay that reflects the soft light of the evening.

4.98 out of 5 average rating, 51 reviews

Cozy Coastal Condo in Wells - Hot Tub & Pool!

5 out of 5 average rating, 11 reviews

Condo in Ogunquit

NEW Classy Ogunquit Retreat! Pools, Walkable!

The kitchen features modern cabinetry with a light grey finish and granite countertops. Stainless steel appliances include a refrigerator, dishwasher, oven, and microwave. A window allows natural light to illuminate the space, and oak flooring runs throughout, providing a warm atmosphere.

4.87 out of 5 average rating, 217 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

4.85 out of 5 average rating, 73 reviews

A calm beach scene is captured at dusk, with gentle waves lapping against the shore. Soft, warm hues of orange and purple dominate the sky, reflecting on the wet sand. The shoreline is outlined by scattered rocks and seaweed, creating a serene coastal atmosphere.

Condo in York

Little Nubble Nook - Beach Condo

4.9 out of 5 average rating, 102 reviews

Starfish Condo Wells Beach

Superhost

A sign displaying 'Sea Breeze Village' and unit number 'C-310' is affixed to a light gray exterior wall. The sign features a simple design, including a small illustration of a lighthouse, providing clear identification for visitors.

4.86 out of 5 average rating, 14 reviews

Awesome get away spot in Wells!

A modern kitchen is showcased with white cabinetry and granite countertops. Stainless steel appliances include a refrigerator, microwave, and dishwasher. Kitchenware is neatly arranged, enhancing the functional space. A light blue wall adds a calm touch, while a throw pillow with 'BEACH.' text provides a decorative element.

4.96 out of 5 average rating, 114 reviews

Relaxing Beachside Condo with Pool at Wells Beach

A bright living area is showcased with a large blue sectional sofa and a stylish glass coffee table. Natural light enters through three windows, illuminating the wooden floor. A television is mounted on the wall, and nautical-themed decor adds a subtle charm to the space.

4.88 out of 5 average rating, 17 reviews

Barefoot in Maine

Other holiday rentals with a pool

Apartment in Kennebunkport

The living area features a modern design with a spacious gray sectional sofa and a sleek wooden coffee table. Soft lighting is provided by two standing lamps flanking the couch. A large window and glass doors allow natural light to fill the space, enhancing the cozy atmosphere.

5 out of 5 average rating, 32 reviews

Maine Coastal Village Getaway

4.91 out of 5 average rating, 77 reviews

Upscale OOB Beach House | Seasonal Heated Pool

A modern kitchen features white cabinetry paired with stainless steel appliances. A large island with four wooden stools provides ample space for dining or work. Natural light fills the area through a window, enhancing the clean, inviting design.

4.97 out of 5 average rating, 72 reviews

Freshly Renovated, Family-Friendly Coastal Cottage

Condo in Old Orchard Beach

A vibrant view captures the amusement park, featuring a large Ferris wheel and colorful attractions. The beach stretches in the background, illuminated by a soft, pastel sunset. A lively crowd gathers below, enjoying the bustling atmosphere of the town square.

5 out of 5 average rating, 19 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

A charming beach house is featured, surrounded by sandy areas and an inviting outdoor space. An aqua parasol provides shade over a picnic table, while white lounge chairs are arranged nearby. The wrap-around porch, adorned with seating, extends from the house, enhancing outdoor relaxation.

4.83 out of 5 average rating, 6 reviews

Oceanfront Cottage 3 in OOB

The cottage exterior features a welcoming entrance with a wooden porch and steps leading to a pink door. Large windows framed in white allow natural light to fill the space, surrounded by well-maintained landscaping with green grass and colorful flowers.

4.93 out of 5 average rating, 41 reviews

Beautiful 2 bedrm cottage in Beach Dreams complex

An outdoor heated pool is surrounded by lounge chairs, with a bright blue water surface reflecting the clear sky. Nearby, white cabanas provide shaded seating. Multi-story buildings are visible in the background, adding to the communal atmosphere of the space.

4.75 out of 5 average rating, 163 reviews

Generic Two Bedroom - Stair access only

A spacious living area features large windows with natural light entering from outside, highlighting the blue walls. Comfortable seating includes a sectional and a leather ottoman. A decorative lamp and stylish clock add to the serene ambiance, while views of the surrounding greenery are visible.