
Holiday rentals with a pool in Kennebunk
Find and book unique homes with a pool on Airbnb
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 €70 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!
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

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.

Summit Vista | 3br Mountain Paradise | Epic Views
Escape to Summit Vista, a classic chalet-style home in the heart of the White Mountains. With 3 bedrooms, 2 baths, a loft, and many thoughtful upgrades, this home is built for comfort, connection, and mountain adventure. Just minutes from Story Land, Attitash, and North Conway, Summit Vista offers access to top ski resorts, hiking trails, restaurants, and shopping. Blending mountain style with modern comfort, Summit Vista celebrates the natural beauty and timeless charm of the White Mountains.

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

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!

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

Faith Lane with community pool

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

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

Sanctum by the Lake

Ski Chalet|Ping-Pong|Fire Pit|5 min -> Slopes

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

Maritime Meadows – Charming Resort-Style Home!

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

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

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

Across from Storyland & Heated Pool

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

Bartlett Condo; Great Views, Resort Access

Spectacular Mountain Views, at Eagle Ridge !

North Conway, Skiing, Hiking, and Storyland

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P
Other holiday rentals with a pool

Maine Coastal Village Getaway

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Freshly Renovated, Family-Friendly Coastal Cottage

Studio Condo, Deck, Pool, Hot Tub, Playground

Walk to Wells Beach! July dates open!

Our Happy Place!

2 BR house, close to Ogunquit, w/ AC + golf cart!

Contemporary Cottage With Ocean View 32
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €211 | €261 | €329 | €150 | €155 | €178 | €225 | €247 | €160 | €160 | €192 | €192 |
| 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
- York Harbor Beach
- Willard Beach
- Crane Beach
- Short Sands Beach
- Scarborough Beach
- North Hampton Beach
- East End Beach
- Footbridge Beach
- Popham Beach State Park
- Cape Neddick Beach
- Gooch's Beach
- King Pine Ski Area
- Gunstock Mountain Resort
- Salisbury Beach
- Hills Beach
- Crescent Beach State Park
- Jenness Beach





