Holiday rentals with a pool in Kennebunk

4.93 out of 5 average rating, 245 reviews

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

Sanctum by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

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, 589 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

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, 153 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, 34 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.

4.9 out of 5 average rating, 102 reviews

Condo in Wells

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, 117 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.

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.

Home in Old Orchard Beach

4.95 out of 5 average rating, 134 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.

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, 28 reviews

Maine Coastal Village Getaway

Experience tranquility at this beautiful condo in Cape Porpoise, Kennebunkport. It offers a modern kitchen, cozy living space, and a stunning deck overlooking Cape Porpoise Harbor. Enjoy the serene landscaping and shared pool. Close to a grocery store, top-notch restaurants, shops, and a scenic walk to Cape Porpoise pier. Just a short drive to Kennebunkport town center, beaches, and Goose Rocks Beach. Book your stay at 15 Langsford Road today for an unforgettable getaway!

4.92 out of 5 average rating, 129 reviews

A spacious living area features a comfortable sectional sofa with patterned upholstery, situated alongside large windows offering expansive views of the waterfront. Natural light floods the room, complemented by warm wooden accents on the ceiling and floor. A dining table for four is placed near the windows.

Cottage in Plum Island

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (open June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Popular amenities for Kennebunk rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 14 reviews

A comfortable living area is depicted, featuring a spacious beige couch adorned with textured pillows. A wooden coffee table is positioned in front, and a round dining table with two chairs is visible. Large glass doors provide an unobstructed view of the Ogunquit River and surrounding nature.

Home in Wells

Ogunquit River Outlook

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

Home in Old Orchard Beach

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.

4.96 out of 5 average rating, 106 reviews

Faith Lane with community pool

Superhost

Home in New Durham

4.71 out of 5 average rating, 17 reviews

Dog Friendly Private Waterfront Luxury Smarthome

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!

Home in Old Orchard Beach

5 out of 5 average rating, 54 reviews

Our Beach House Getaway

4.97 out of 5 average rating, 60 reviews

Home in Standish

Unique Church Stay • Sebago Lake • Pool • Fire Pit

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

Condo rentals with a pool

4.98 out of 5 average rating, 51 reviews

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.

Condo in Wells

Cozy Coastal Condo in Wells - Hot Tub & Pool!

5 out of 5 average rating, 11 reviews

Condo in Ogunquit

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

4.98 out of 5 average rating, 47 reviews

A view of the ocean is framed by large windows, displaying tranquil blue waters and sandy beaches. The image captures the shoreline and nearby buildings, offering a glimpse of the vibrant beach atmosphere.

Condo in Hampton Beach

Ocean View - Steps to the Beach!

4.84 out of 5 average rating, 100 reviews

An aerial view of Hampton Beach highlights the proximity of the condo to the beach and nearby attractions. The coastline stretches out with sandy shores and a vibrant blue ocean. Nearby buildings and roadways are visible, providing a sense of the community and access to the area.

Condo in Hampton Beach

Steps from Beach | Pool | Parking | Large Deck

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, 17 reviews

Condo in Old Orchard 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.

Condo in Wells

4.86 out of 5 average rating, 14 reviews

Awesome get away spot in Wells!

4.96 out of 5 average rating, 125 reviews

A living room showcases a cozy seating area with two black sofas facing a television. A coffee table is centrally placed, adorned with a candle and a snack. A brick fireplace adds warmth, while natural light filters through the dual windows, dressed with light curtains.

Condo in Conway

Cozy, clean, 2nd floor condo in Conway, NH!

5 out of 5 average rating, 18 reviews

Condo in Conway

Peaceful Pines Saco River Getaway

Other holiday rentals with a pool

4.93 out of 5 average rating, 55 reviews

Make this family-friendly cottage your summer spot

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

4.91 out of 5 average rating, 92 reviews

A weathered wooden dock extends over a tranquil pond, surrounded by lush greenery and trees. Flickering lanterns are placed along the edges, adding a soft glow to the quiet natural setting. The scene reflects the changing colors of foliage in the background.

Guest suite in Biddeford

Heron's Hide-Away

A modern kitchen features a sleek countertop with a variety of fresh ingredients arranged on plates. A coffee maker is visible in the background, alongside a stainless-steel kitchen appliance. Natural light enters through a window, illuminating the stylish grey and white color scheme.

4.9 out of 5 average rating, 29 reviews

Beautifully renovated 2-bedroom cottage

The exterior of the studio is shown, featuring a main entrance with large windows that provide natural light. A charcoal grill is positioned nearby, along with two blue adirondack chairs on a simple porch. The area is surrounded by gravel and concrete, with green grass visible in the background.

4.93 out of 5 average rating, 69 reviews

Cottage in Wells Maine

4.95 out of 5 average rating, 57 reviews

A serene saltwater pool is set within a natural landscape, featuring smooth stone borders and surrounded by green trees. The clear water reflects the blue sky, creating a calming environment for relaxation. Nearby, a stone patio is visible, enhancing the outdoor area.

Cabin in Wakefield

Cabin in the woods with pool and lake access

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