
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 €78 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

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

Four Story Townhouse With Ocean View 55
Our newly re-done townhouse is available year-round featuring a beautiful kitchen/living area with gas fireplace and relaxing balconies. This townhouse is equipped with gas heat, central air conditioning, ceiling fans, a fully equipped kitchen with a dishwasher, a gas grill, cable TV, Wi-Fi, and more! The 3-bedroom townhouses come with an additional Bedroom on the 4th floor. Feature 2-1/2 bathrooms and a washer and dryer. Private parking for 2 vehicles. Pools/hot tub are shared with community.

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!

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.

Luxury Retreat In Back Cove | 10 Min to Downtown
Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Kennebunk's Charming Beach Home
Exceptionally 2 weeks left this summer! Book fast! Well located, our charming cozy home is just an easy stroll, less than 1 mile away from Mother's beach. 5 min. drive from all the Kennebunkport shops and restaurants. 5 comfortable bedrooms and 2 1/2 bathrooms. The private backyard is perfect to enjoy and feel the sea breeze. Enjoy the hot tub and the heated pool, volley ball court, fire pit, plenty of space for parking. A great place to create memories with yours!
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

The Lodge at Hidden Pines

BRAND NEW 2026: East Coastin' 2 bed/1 bath Cottage

Sanctum by the Lake

2BR, Sea & Relax w/ Wells Reserve View

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Condo rentals with a pool

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

Small ’N Moody | Near Moody Beach & Ogunquit

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

Spectacular Mountain Views, at Eagle Ridge !

Elevate Your Adventure: Book Slope side Now!

•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

Freshly Renovated, Family-Friendly Coastal Cottage

Steps to Wells & views of Rachel Carson Preserve

Painted Tides Cottage in Wells | Pool | Near Beach

Studio Condo, Deck, Pool, Hot Tub, Playground

Surf Inn #2

Paradise Found Minutes from Ogunquit | Heated Pool

Luxurious Penthouse- Ski-In/Out Condo at Cranmore

Cottage in Wells Maine
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €209 | €258 | €326 | €216 | €191 | €190 | €222 | €244 | €158 | €158 | €190 | €190 |
| 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
- Short Sands Beach
- York Harbor Beach
- North Hampton Beach
- Scarborough Beach
- Crane Beach
- Footbridge Beach
- Cape Neddick Beach
- East End Beach
- Gooch's Beach
- Jenness Beach
- Salisbury Beach
- King Pine Ski Area
- Hills Beach
- Gunstock Mountain Resort
- Popham Beach State Park
- Wolfe's Neck Woods State Park





