
Vacation rentals with a pool in Kennebunk
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Kennebunk

Total vacation rentals
Explore 220 vacation rentals in Kennebunk

Nightly prices starting at
Kennebunk vacation rentals start at $126 CAD per night before taxes and fees

Verified guest reviews
Over 4,240 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
220 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!
Top-rated rentals with a pool in Kennebunk
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
You 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, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Large Historic 7 Bedroom home with Pool & Hot Tub
Very Unique, large historial home in beautiful Falmouth, Maine. Originally built in 1725, this nearly Three-Hundred-Year old Federal-style farmhouse still retains some original features. In the early 1900's, this home served as a bootleg hard cider mill, and more recently, an oriental rug business. Great place for families with kids to stay while enjoying coastal Maine and Portland. Less than a mile from Portland and 4 miles from the historic Old Port district. (Hot tub open year-round)!

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

Luxury Coastal 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

Super cute one bedroom with hot tub and pool.
This cottage is ideally located just minutes from the beach and the beautiful Rachel Carson National Wildlife Refuge. You'll also find numerous local restaurants serving fresh Maine lobster and other coastal favorites nearby. Whether you're looking for adventure or relaxation, there are plenty of activities, including hiking, biking, kayaking, sunbathing, and scenic beach walks. From exploring nature trails to enjoying a sunset stroll along the shore, this location offers something for everyone.

Beach House w/ Pool · Fire Pit · Dual Kitchens
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!

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.

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.

OOB Oasis: 6BR 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, new hot tub and sparkling in-ground pool; perfect for summer fun, fall gatherings, or relaxing after a day at the beach.

Steps to Wells Beach + Pool | Coastal Retreat
Stay steps from Wells Beach in this renovated coastal condo with an onsite pool, clean modern interior, and prime walkable location off Atlantic Avenue. Walk to the sand in minutes, enjoy the ocean air from your patio, relax by the pool, and explore nearby shops, dining, playground, and arcade. Perfect for couples, small families, or a small group, this one bedroom condo makes an easy Southern Maine escape for visiting Wells, Ogunquit, Kennebunkport and the classic New England coast!
Popular amenities for Kennebunk rentals with a pool
House rentals with a pool

Faith Lane with community pool

Beach Plum-Elegant Coastal Escape

1 mile to OOB pier | Outdoor fire pit | Game room

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast

Sanctum by the Lake

2BR, Sea & Relax w/ Wells Reserve View

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

Downtown North Conway private pool-hot tub
Condo rentals with a pool

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

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

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Elevate Your Adventure: Book Slope side Now!

North Conway, Skiing, Hiking, and Storyland

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

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P

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

Maine Coastal Village Getaway

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Four Story Townhouse With Ocean View 55

Just Beachy New Rental

Freshly Renovated, Family-Friendly Coastal Cottage

Small ’N Moody | Near Moody Beach & Ogunquit

Studio Condo, Deck, Pool, Hot Tub, Playground

Paradise Found Minutes from Ogunquit | Heated Pool
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $336 CAD | $416 CAD | $526 CAD | $240 CAD | $247 CAD | $285 CAD | $359 CAD | $394 CAD | $255 CAD | $255 CAD | $307 CAD | $307 CAD |
| 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 |
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- Sebago Lake
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- North Hampton Beach
- Scarborough Beach
- Crane Beach
- Footbridge Beach
- Cape Neddick Beach
- East End Beach
- Gooch's Beach
- Popham Beach State Park
- Salisbury Beach
- King Pine Ski Area
- Jenness Beach
- Gunstock Mountain Resort
- Hills Beach
- Crescent Beach State Park





