
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.

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

Wells Maine Home with a View
Our Contemporary Cottages, at Seagull, gracefully sits on a grassy 11 acre bluff with panoramic views of the Rachel Carson Refuge and the Atlantic Ocean. This tastefully decorated cottages offer air conditioning, heat, ceiling fans, fully equipped kitchen with dishwasher, gas grill, cable TV, skylights, and a large screened in porch with sliding glass doors opening into the livingroom and master bedroom. Cottage has a great pool/hot tub. WIth ocean view and comfortably accommodates six guests.

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only 10 min to downtown. Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by one of our fire pits, our half-acre yard offers a tranquil stay. The apartment boasts a newly renovated bathroom, radiant heated floors in both kitchen & bath, and a chef's kitchen. This grand apartment won't disappoint. L2 EV charging outlet on site #allarewelcome

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

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
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 seasonal 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, Goose Rocks Beach, and other beaches. Book your stay at 15 Langsford Road today for an unforgettable getaway!

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.

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
Popular amenities for Kennebunkport rentals with a pool
House rentals with a pool

Ogunquit River Outlook

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Fantastic Kittery Home with Pool

Pool and walking distance to beaches! Amenities!

Steps to Wells & views of Rachel Carson Preserve

Our Beach House Getaway

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

Maritime Meadows - Charming Resort-Style Home!
Apartment rentals with a pool

NEW Classy Ogunquit Retreat! Pools, Walkable!

Two-Bedroom Condo on the Wells/Ogunquit town-line

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Little Nubble Nook - Beach Condo

Steps from Beach | Pool | Parking | Large Deck

Condo in Old Orchard Beach

Awesome get away spot in Wells!

Cozy, clean, 2nd floor condo in Conway, NH!
Other holiday rentals with a pool

1 bedroom with pool, walk to the beach.

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

Beautiful 2 bedrm cottage in Beach Dreams complex

Beautifully renovated 2-bedroom cottage

Cabin in the woods with pool and lake access

Sleeps 6, Pool, Hot Tub, Arcade, Gym, Near Beach

Beach Dreams Cottage - Wells, ME

2 BR house, close to Ogunquit, w/ AC + golf cart!
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 € 102 per night before taxes and fees

Verified guest reviews
Over 300 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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- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Scarborough Beach
- Crane Beach
- York Harbor Beach
- Popham Beach State Park
- North Hampton Beach
- Willard Beach
- East End Beach
- Short Sands Beach
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Gunstock Mountain Resort
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Footbridge Beach
- Bear Brook State Park
- Funtown Splashtown USA
- Jenness Beach





