
Holiday rentals with a pool in Kennebunkport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kennebunkport
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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

"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

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

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.

NoCo Village King/Jacuzzi.
Welcome to Village Place at the Eastern Slope Inn! Must be 21 to check-in, $40 authorization taken at check-in (not an actual charge), no cats. IF YOUR PUP IS JOINING YOU, please provide advanced notice, a $25/night pet fee for the first 4 nights, RABIES RECORDS, and a crate if you must leave them behind. One dog is permitted per room, no cats, thanks for understanding. Located halfway between The Eastern Slope Inn and Cranmore Mountain, this second floor unit is walking distance to it all!

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!*

KimBills’ on the Saco
KimBills' is a newly renovated, cozy, first floor condo located at Attitash Mtn. Village, just minutes from the Saco River. Full kitchen well stocked with necessities, gas fireplace, A/C, Murphy bed and pull-out sofa bed with new, comfortable mattresses. Cable/internet, 55" TV, & board games. Large deck with lighting. Guests enjoy full use of all Attitash Mtn. Village amenities including river access, pools, sauna, hot tubs, tennis & basketball. Close to shopping and area attractions.

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.

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 house living close to Ogunquit center!
The cottage was completely remodeled in spring of 2018. It 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!

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 Kennebunkport rentals with a pool
House rentals with a pool

Faith Lane with community pool

Upscale OOB Beach House | Seasonal Heated Pool

The Lodge at Hidden Pines

Stunning Beach House with an in-ground pool!

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

2BR, Sea & Relax w/ Wells Reserve View

The Goodwin House (East) 420 Friendly

There's No Place Like Home
Apartment rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

AttitashResort! 1-flr, studio, secure check-in

Slope-side White Mountain Oasis

Spectacular Mountain View’s

Elevate Your Adventure: Book Slope side Now!

•Spectacular Views•Modern•Spacious•Pools (in/out)

Relaxing Beachside Condo with Pool at Wells Beach

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
Other holiday rentals with a pool

Treehouse Farm - Sebago

Four Story Townhouse With Ocean View 66

Pool and walking distance to beaches! Amenities!

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront

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

Centrally located Ocean Towers condo in Ogunquit

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

Brand new 2 b/r tiny home, 5 minute walk to beach
Quick stats about holiday rentals with a pool in Kennebunkport

Total holiday rentals
Explore 20 holiday rentals in Kennebunkport

Nightly prices starting at
Kennebunkport holiday rentals start at € 119 per night before taxes and fees

Verified guest reviews
Over 230 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
20 of Kennebunkport holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kennebunkport rentals

4.8 Average rating
Kennebunkport stays are highly rated by guests – averaging 4.8 out of 5!
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