Holiday rentals with a pool in Biddeford

4.87 out of 5 average rating, 590 reviews

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

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

4.83 out of 5 average rating, 163 reviews

An expansive in-ground pool is surrounded by a spacious wooden deck, featuring comfortable lounge chairs. The house, with gray siding, is visible in the background, flanked by trees that provide privacy. Soft clouds pass overhead, contributing to a tranquil outdoor setting.

Home in Kennebunk

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!

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

A grassy area features seating made up of Adirondack chairs and a patio table set, facing a row of cottages with large windows. The clear sky above is dotted with clouds, complementing the peaceful surroundings.

4.93 out of 5 average rating, 210 reviews

Wells Maine Home with a View

Our Contemporary Cottages, at Seagull, gracefully sits on a grassy 11 acre bluff with panoramic views of the Rachel Carson Refuge and the Atlantic Ocean. This tastefully decorated cottages offer air conditioning, heat, ceiling fans, fully equipped kitchen with dishwasher, gas grill, cable TV, skylights, and a large screened in porch with sliding glass doors opening into the livingroom and master bedroom. Cottage has a great pool/hot tub. WIth ocean view and comfortably accommodates six guests.

Apartment in Kennebunkport

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.

5 out of 5 average rating, 36 reviews

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

4.98 out of 5 average rating, 58 reviews

Home in Biddeford

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

Relax with a private pool, spacious deck, and easy access to Maine’s beautiful seacoast. Perfect for families and groups to enjoy outdoor living. ✱ Sleeps 10–12, cozy with 12 ✱Private 35x18 pool with floaties and lounge chairs ✱Deck with grill, mini fridge, and seating ✱Spacious 2100 sq ft open layout ✱Fully stocked kitchen, coffee and tea ✱Fast WiFi and smart TVs ✱Foosball, games, and record player ✱Comfortable beds with quality linens ✱Crib and high chair available ✱Ample off street parking

4.9 out of 5 average rating, 102 reviews

Starfish Condo Wells Beach

Enjoy the amazing sunrise as well as marsh and ocean views from this spacious just renovated one and a half bedroom condo with queen bed and queen Murphy bed. Fully equipped kitchen with granite counter tops and stainless steel appliances. Updated full bath with tub. Located within walking distance to many local area restaurants. After a fun filled day on the beach relax by the salt water pool or in the hot tub. Shared gas grill, picnic area, playground and basketball hoop. Parking for one car

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.

4.97 out of 5 average rating, 483 reviews

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

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

Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by the fire pit, our half-acre yard offers a tranquil stay. The apartment has a chef's kitchen, radiant heat floors in the kitchen and bathroom. Use of the living room daybed linens may incur a charge. Please ask. There is a L2 EV charging outlet. #allarewelcome

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.

4.95 out of 5 average rating, 135 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.

4.93 out of 5 average rating, 132 reviews

The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.

Guest suite in East End

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Munjoy Hill is Portland's premiere neighborhood. Enjoy ocean views along the Promenade. Share our seasonal private pool/hot tub with us from May thru Oct (dates vary). We have a swing set, lounge chairs, grill, play cornhole, tennis (we supply racquets/balls) watch baseball, basketball or take a walk to the playground close by. A short walk to East End Beach and the waterfront trail lead you to the famous Old Port. This property is one of a kind in the city

Popular amenities for Biddeford 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

5 out of 5 average rating, 54 reviews

Our Beach House Getaway

4.97 out of 5 average rating, 61 reviews

Home in Standish

Unique Church Accommodation • Sebago Lake • Pool • Fire Pit

4.8 out of 5 average rating, 30 reviews

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

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, 6 reviews

Home in Arundel

Designers Dream Home with 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

Apartment rentals with a pool

Superhost

An aerial view showcases the single-level condo building set one block back from the beach. A pool is visible in the center, surrounded by greenery. The extensive beach stretches out in the background, with several beachgoers enjoying the sunny day.

Apartment in Old Orchard Beach

4.83 out of 5 average rating, 12 reviews

30 second walk to Beach- Pool-Outdoor Shower

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!

Apartment in Old Orchard Beach

An aerial view shows Old Orchard Beach, capturing sandy shores and the nearby pier. The image also features a heated saltwater pool with inflatable floaties, alongside a bright sleeping area with two full beds arranged with neutral linens and subtle decor.

5 out of 5 average rating, 11 reviews

Steps to Beach, Pier, Park | Condo with Pool • 11

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.

Apartment in York

Little Nubble Nook - Beach Condo

4.98 out of 5 average rating, 64 reviews

The spacious studio features light-colored walls and flooring, with two beds and a small dining area. Decorative coastal artwork adorns the walls, and a blue area rug adds a touch of color. A kitchenette and seating area are visible, enhancing functionality.

Apartment in Ogunquit

Pretty Boutique Studio, Pools, Walk to Everything!

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 serene view of the surrounding landscape is captured at sunset, with soft hues of orange and pink illuminating the sky. A lush green area is visible, with distant outlines of trees and water reflecting the tranquil scene.

4.92 out of 5 average rating, 26 reviews

Seaside Condo w/stunning views, 2 Queen sized beds

Superhost

A small dining area features a light wood table set with placemats, accompanied by two white chairs. Natural light is welcomed through two large windows adorned with soft, sheer curtains. A cozy seating area with a light-colored sofa is visible in the background.

4.86 out of 5 average rating, 44 reviews

Drake's Island Beach Area Studio

Other holiday rentals with a pool

4.97 out of 5 average rating, 58 reviews

A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.

Home in Kittery

Fantastic Kittery Home with Pool

Flat in Old Orchard Beach

4.87 out of 5 average rating, 63 reviews

Sea Salt Stay

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

5 out of 5 average rating, 9 reviews

A charming white cottage is depicted with a well-maintained lawn and surrounding greenery. A small porch is visible at the entrance, complemented by simple outdoor seating. The clear blue sky provides a bright backdrop, while the cottage features a symmetrical design with a gable roof.

Home in Wells

Cozy Beach Cottage - Wells, ME

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

5 out of 5 average rating, 10 reviews

A two-story condo is shown with a light blue exterior. Several green shrubs and plants surround the building, and a wooden staircase leads to an entrance on the upper level. The clear blue sky provides a bright backdrop.

Townhouse in Wells

Sleeps 6, Pool, Hot Tub, Arcade, Gym, Near Beach

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.

4.98 out of 5 average rating, 66 reviews

2 BR house, close to Ogunquit, w/ AC + golf cart!