Vacation rentals with a pool in Kennebunk

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Top-rated rentals with a pool in Kennebunk

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
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, 658 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 favourite
A two-story home is set amidst a landscaped lawn featuring flowering shrubs. The gray exterior is complemented by white window shutters and a front porch. A paved driveway curves around the property, leading to a side entrance, surrounded by mature trees under a partly cloudy sky.
Home in Kennebunk
4.78 out of 5 average rating, 51 reviews

Kennebunk's Charming Beach Home

Well located, our charming cozy home is just an easy stroll, less than 1 mile away from Mother's beach. 5 minutes drive from all the shop and restaurants of Kennebunkport. There are 5 comfortable bedrooms, 4 upstairs and 1 on the main floor and 2 bathrooms. The private backyard is perfect to enjoy and feel the sea breeze. Enjoy the hot tub and the heated pool, volley ball court, fire pit, plenty of space for parking. A great place to create memories with your friends and family! Contact us!

Guest favourite
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, 582 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

Top guest favourite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in North Deering
4.96 out of 5 average rating, 150 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

Top guest favourite
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.
Apartment in Rosemont
4.97 out of 5 average rating, 457 reviews

Apt in Victorian Mansion w/ Hot Tub & Parking

Mixing contemporary styling with old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our pool or relax by the fire pit, our half-acre yard offers a tranquil space for all. The apartment has a chef's kitchen, dining, and living room with gas fireplace. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

Guest favourite
A bright studio space features light blue walls and a combination of yellow and navy decor. A spacious bed with a navy bedspread is positioned next to a cozy gray couch. Natural light floods the room from large windows and a door providing access to the outdoors.
Apartment in Wells
5 out of 5 average rating, 9 reviews

Studio Condo, Deck, Pool, Hot Tub, Playground

Seabreeze Studio is a cozy and comfortable studio condo that sleeps up to 4 guests with a queen bed and a sleeper sofa. It features a small kitchen and a large deck, where you can enjoy your morning coffee or dinner outside. A grill is also provided. Community has an in-ground pool and hot tub, playground, basketball court, horseshoes, and more. Conveniently located on Route 1 in Wells, just 1.5 miles from the beach and within walking distance to restaurants, shopping, and local attractions.

Guest favourite
Home in Arundel
5 out of 5 average rating, 5 reviews

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.

Guest favourite
A sandy beach area is visible, surrounded by several red adirondack chairs arranged around a small fire pit. A black lounge chair sits nearby. A pontoon boat is docked on the water, with a paddle board lying on the grass beside the seating area.
Home in Barnstead
4.86 out of 5 average rating, 115 reviews

Locke Lake Ski & Swim

Completely renovated home with private beach and waterfront. The water drops off gently making it great for young children. Variety of rafts, beach toys, kayaks, paddle boards, pedal and row boat available for use. Great fishing in the summer, and ice fishing in the winter. Outdoor deck is wonderful for entertaining. Seasonal game room in garage with shuffleboard and more. Located about 15 mins south of Lake Winnipesaukee and 30 mins from Gunstock Mountain. *Linens and Towels now included!*

Guest favourite
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.
Apartment in Wells
4.91 out of 5 average rating, 33 reviews

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

Welcome to 'Well Ashore', a charming 1-bedroom, 1-bath efficiency condo just 1 mile from the breathtaking Wells Beach- One of Maine's 7 mile pristine sandy beaches. Ideal for couples or small families, this cozy retreat features a serene, nautical-inspired ambiance perfect for relaxation. Our condo is 4 miles from The Marginal Way, one of New England's most cherished coastal walks. This 1.25 mile scenic path offers stunning ocean views with benches, and an easy access to downtown Ogunquit.

Top guest favourite
A charming red schoolhouse, dating back to 1866, is surrounded by tall trees and a well-kept grassy area. The structure features white trim, large entrance doors, and a bell tower, evoking a sense of history and nostalgia.
Place to stay in Shapleigh
5 out of 5 average rating, 101 reviews

Romantic New England Historic Schoolhouse c1866

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.

Top guest favourite
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
4.95 out of 5 average rating, 165 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.

Guest favourite
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.
Apartment in Kennebunkport
5 out of 5 average rating, 14 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!

Popular amenities for Kennebunk rentals with a pool

When is the best time to visit Kennebunk?

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Avg. price$320 CAD$238 CAD$320 CAD$239 CAD$246 CAD$284 CAD$358 CAD$393 CAD$255 CAD$280 CAD$206 CAD$248 CAD
Avg. temp-4 °C-3 °C1 °C7 °C13 °C18 °C21 °C21 °C16 °C10 °C4 °C-1 °C

Quick stats about vacation rentals with a pool in Kennebunk

  • Total vacation rentals

    Explore 190 vacation rentals in Kennebunk

  • Nightly prices starting at

    Kennebunk vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 4,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    190 of Kennebunk vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Kennebunk rentals

  • 4.8 Average rating

    Kennebunk stays are highly rated by guests—averaging 4.8 out of 5!

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