
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.

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.

Sanctum by the Lake
Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

"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

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.

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

2BR, Sea & Relax w/ Wells Reserve View

Designers Dream Home with Pool!

Downtown North Conway private pool-hot tub

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

Small ’N Moody | Near Moody Beach & Ogunquit

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

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
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

Studio Condo, Deck, Pool, Hot Tub, Playground

Newly Renovated Studio Downtown!

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





