
Vacation 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.

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

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!

"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

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

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

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!

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.

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.

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!

Romantic Bungalow w/ Pool, Hot Tub & Parking
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

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

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 Kennebunkport rentals with a pool
House rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Home Near Beaches & Fun

Ogunquit River Outlook

Faith Lane with community pool

The Lodge at Hidden Pines

Stunning Beach House with an in-ground pool!

Cozy Beach Cottage - Wells, ME

Cozy Maine Church Retreat Near Portland • Fire Pit

Walk to Downtown NoCo w Private pool and hot tub!
Condo rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

Ocean View - Steps to the Beach!

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Steps from Beach | Pool | Parking | Large Deck

Our Happy Place!

Elevate Your Adventure: Book Slope side Now!

Awesome get away spot in Wells!
Other vacation rentals with a pool

Cottage by the sea

Freshly Renovated, Family-Friendly Coastal Cottage

Charming Condo in Wells

Heron's Hide-Away

Beautifully renovated 2-bedroom cottage

Ogunquit Downtown- 5 Mins from Playhouse and Beach

Cabin in the woods with pool and lake access

Sleeps 6, Pool, Hot Tub, Arcade, Gym, Near Beach
Quick stats about vacation rentals with a pool in Kennebunkport

Total vacation rentals
Explore 20 vacation rentals in Kennebunkport

Nightly prices starting at
Kennebunkport vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

Verified guest reviews
Over 280 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
20 of Kennebunkport vacation rentals include wi-fi access

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

4.9 Average rating
Kennebunkport stays are highly rated by guests—averaging 4.9 out of 5!
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- Hampton Beach
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