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

Ocean Beach Cottage Wells, ME
Your newly renovated unique private corner lot cottage offers spectacular unobstructed marsh views to ocean included in top 10 US beaches (Boston travel Ogunquit best beaches)Full kitchen, granite countertops, breakfast bar, new appliances, dishwasher, queen bed sleeps 2 adults, roomy L shaped sofa w/ additional sheets upon request for one child or one adult. Bassinet for infant under 20 lbs on request. Keurig/complimentary coffee, tea. Hairdryer, 2 smart TV's ready for streaming, private WIFI

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

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.

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!
Popular amenities for Kennebunk rentals with a pool
House rentals with a pool

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Faith Lane with community pool

Steps to Wells & views of Rachel Carson Preserve

The Lodge at Hidden Pines

Our Beach House Getaway

Cozy Beach Cottage - Wells, ME

Maritime Meadows - Charming Resort-Style Home!

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

Cozy Coastal Condo in Wells - Hot Tub & Pool!

NEW Classy Ogunquit Retreat! Pools, Walkable!

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

Little Nubble Nook - Beach Condo

Steps from Beach | Pool | Parking | Large Deck

Awesome get away spot in Wells!

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

Cozy Family Retreat with Saco River Access
Other holiday rentals with a pool

Beach Dreaming

Paradise Found Minutes from Ogunquit | Heated Pool

Beautifully renovated 2-bedroom cottage

Cottage in Wells Maine

Cabin in the woods with pool and lake access

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

Luxury Retreat In Back Cove | 10 Min to Downtown

Beach Dreams Cottage - Wells, ME
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £176 | £218 | £275 | £125 | £129 | £149 | £188 | £206 | £134 | £134 | £161 | £161 |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about holiday rentals with a pool in Kennebunk

Total holiday rentals
Explore 200 holiday rentals in Kennebunk

Nightly prices starting at
Kennebunk holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 4,110 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
200 of Kennebunk holiday 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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- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Scarborough Beach
- Crane Beach
- York Harbor Beach
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- Wolfe's Neck Woods State Park
- Crescent Beach State Park
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- Funtown Splashtown USA
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