Holiday rentals with a pool in Kennebunk

4.93 out of 5 average rating, 246 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.

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

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, 34 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

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

Apartment 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, 118 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.

5 out of 5 average rating, 28 reviews

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.

Flat in Kennebunkport

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!

4.93 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

Ogunquit River Outlook is a delightful two-bedroom condo overlooking the Ogunquit River and the Atlantic Ocean. Enjoy a fully equipped home. Newly designed full bath and in-unit washer and dryer add convenience. Enjoy the sunrise on the deck or prepare meals in the kitchen. Community heated pool and Ogunquit River access for kayaking. Just steps from Ogunquit, local shops, eateries, and some of Maine's finest beaches. Parking for one car only

4.97 out of 5 average rating, 153 reviews

A charming cottage features light blue siding and white trim, complemented by a small porch with railing. Surrounding trees provide shade, while a picnic table and grill are positioned in the grassy yard. Stone landscaping offers a natural backdrop to the cottage.

Cottage in York

Tiny house living close to Ogunquit center!

This tiny house is one of 21 cottages built in 1920. The back of the cottage is a rolling meadow and woods. It feels secluded, yet you are only a mile from all the wonderful happenings in Downtown Ogunquit, Perkins Cove & Ogunquit beach. Come enjoy the beach, shopping and amazing restaurants. Check out the Nubble Lighthouse, shop the outlets in Kittery or walk around Portsmouth NH. This tiny cabin is convenient to so much. Come rejuvenate!

Popular amenities for Kennebunk rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 40 reviews

A cozy outdoor area is illuminated by soft string lights and features circular seating around a stone fire pit. The backdrop showcases a charming two-story home nestled among trees, with warm light glowing from the windows, creating an inviting ambiance for evening gatherings.

Home in Sebago

Treehouse Farm - Sebago

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

4.98 out of 5 average rating, 63 reviews

An indoor pool is surrounded by light blue walls and gray tile accents. Natural light filters in through large windows, illuminating the water's surface. Steps lead from the pool to a door that opens to the outside area.

Home in Hampton

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Superhost

A spacious living area features a classic red-brick fireplace as a focal point. Dark leather seating is arranged around a central coffee table, while a patterned area rug adds texture to the hardwood floor. Light from overhead fixtures illuminates the room.

Home in Hampton Beach

4.88 out of 5 average rating, 8 reviews

Ocean Breeze Hideaway

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!

4.95 out of 5 average rating, 21 reviews

A light-filled living room features a soft white couch adorned with blue and aqua cushions. A cozy navy chair complements a glass-top coffee table, which is surrounded by patterned poufs. An air conditioning unit and a television are positioned for convenience, enhancing the inviting space.

Home in Hampton

Sleeps 10-4/2 Cozy Beach Cottage, Pool, Porch, BBQ

Home in Old Orchard Beach

5 out of 5 average rating, 54 reviews

Our Beach House Getaway

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

Apartment 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.

Apartment in Wells

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Apartment in Old Orchard Beach

A cozy living area is presented with two stylish armchairs and a matching sofa, all decorated with patterned cushions. A round coffee table sits in the center, resting on a textured area rug. Large windows allow for natural light and views of the ocean.

4.83 out of 5 average rating, 59 reviews

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Apartment in Hampton Beach

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.

4.84 out of 5 average rating, 100 reviews

Steps from Beach | Pool | Parking | Large Deck

Apartment 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

5 out of 5 average rating, 14 reviews

The kitchen area features white cabinetry and a black countertop, with modern appliances including a refrigerator and microwave. A coffee maker and other cooking tools are arranged on countertops. A cozy seating area is highlighted by a sofa adorned with a decorative pillow.

Apartment in Ogunquit

Centrally located Ocean Towers condo in Ogunquit

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.

Apartment 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.

Apartment in Conway

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

4.92 out of 5 average rating, 138 reviews

A serene view of a calm river surrounded by lush greenery. Gentle slopes lead to sandy banks, while trees provide a natural border on either side. The water reflects the blue sky above, creating a peaceful ambiance ideal for outdoor relaxation.

Apartment in Conway

Cozy Family Retreat with Saco River Access

Other holiday rentals with a pool

4.92 out of 5 average rating, 37 reviews

A cozy bedroom features a spacious bed dressed in fresh white linens with a nautical-themed throw blanket. Two framed black-and-white photographs are displayed above the bed. Soft lighting is provided by two bedside lamps, creating a calm, restful environment.

Flat in Wells

Everything's "Well Ashore"- 1 mile to Wells Beach!

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

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, 92 reviews

A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.

Flat in Back Cove

Luxury Retreat In Back Cove | 10 Min to Downtown

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!

The exterior of a white cottage is presented, featuring a red wooden deck and a picnic table with benches. Two windows provide natural light, and a covered entryway leads into the home. The cottage is surrounded by well-kept grassy areas.