
Vacation 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.

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
Welcome to your Ogunquit Oasis, a luxurious 5-bedroom beach house located on the edge of Ogunquit Village. Walk to the beach, restaurants, Perkins Cove, Marginal Way & everything in Ogunquit! The house features a heated pool that reaches 104 degrees, ideal for all seasons. Built in 2014, the house includes central air, three Ultra HD TVs, and wireless speakers. The dining table seats 10, with an outdoor living room, grill, & gas firepit. Each spacious bedroom offers plush bedding & ceiling fans.

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

"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 eateries and breweries. 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

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.

Everything's "Well Ashore"- 1 mile to Wells Beach!
Welcome to 'Well Ashore', a charming 1-bedroom, 1-bath efficiency condo just 1 mile from the breathtaking Wells Beach- One of Maine's 7 mile pristine sandy beaches. Ideal for couples or small families, this cozy retreat features a serene, nautical-inspired ambiance perfect for relaxation. Our condo is 4 miles from The Marginal Way, one of New England's most cherished coastal walks. This 1.25 mile scenic path offers stunning ocean views with benches, and an easy access to downtown Ogunquit.

Our Happy Place!
Our newly renovated coastal themed unit is located one mile from beautiful Wells Beach and directly behind Maine's famous Congdon's Doughnuts. The dining options are endless whether you're looking for something as casual as a food truck or overlooking the sunset from Billy's Chowder House; there's something for everyone. Please note, the pool, hot tub and outdoor amenities are typically available Memorial Day through early October. Guests must bring their own queen sheets and bath towels.

Romantic New England Historic Schoolhouse c1866
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

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.

OOB Oasis - Spacious 5BR private Retreat w/ Pool
Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built retreat 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.

Tower Suite w/ Hot Tub, W/D, & Parking
This newly renovated, gorgeous, spacious suite, located on the 3rd floor of our 1865 mansion, is just 10 mins to downtown and the airport. Relax by the firepit or soak in our hot tub and enjoy our gardens. We are owner-operated. The suite includes a newly renovated bath with rain shower and radiant floor heating; W/D; lounge and kitchenette w/ work table; and a large bedroom. Our half-acre yard provides ample space for privacy. Level 2 EV station is available #allarewelcome

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 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, beaches, and Goose Rocks Beach. Book your stay at 15 Langsford Road today for an unforgettable getaway!

Steep Falls Escape, river & falls just steps away
Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.
Popular amenities for Kennebunk rentals with a pool
House rentals with a pool

Treehouse Farm - Sebago

Faith Lane with community pool

Locke Lake Ski & Swim

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

Cozy Maine Church • Fire Pit • Hammock • WoodStove

The Goodwin House (East) 420 Friendly

2BR, Sea & Relax w/ Wells Reserve View

Old Falls Retreat-4BR w Gorgeous River View & Pool
Condo rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Stylish Designer Retreat on Langsford with Pool

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

Steps from Beach | Pool | Parking | Sleeps 6

Condo in Old Orchard Beach

Centrally located Ocean Towers condo in Ogunquit

The Ocean's Belle

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

Goose Rocks Getaway

Sea Salt Stay

Freshly Renovated, Family-Friendly Coastal Cottage

Cozy Beach Cottage - Wells, ME

"Secret Summer" Savings

Paradise Found Minutes from Ogunquit | Heated Pool

Summertime Oasis with Inground Pool!

Ogunquit Downtown- 5 Mins from Playhouse and Beach
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 199 | € 148 | € 199 | € 148 | € 153 | € 176 | € 222 | € 244 | € 158 | € 174 | € 128 | € 154 |
| 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 vacation rentals with a pool in Kennebunk

Total vacation rentals
Explore 190 vacation rentals in Kennebunk

Nightly prices starting at
Kennebunk vacation rentals start at € 52 per night before taxes and fees

Verified guest reviews
Over 4,120 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
190 of Kennebunk vacation rentals include wi-fi 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
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Sands Beach
- Popham Beach State Park
- Crane Beach
- Popham Beach, Phippsburg
- Weirs Beach
- Jenness State Beach
- Rye North Beach
- North Hampton Beach
- East End Beach
- Dunegrass Golf Club
- Funtown Splashtown USA
- Salisbury Beach State Reservation
- King Pine Ski Area
- Willard Beach
- Wolfe's Neck Woods State Park
- Short Sands Beach
- Wentworth by the Sea Country Club
- Cliff House Beach




