
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 220 holiday rentals in Kennebunk

Nightly prices starting at
Kennebunk holiday rentals start at $157 NZD per night before taxes and fees

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

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
220 of Kennebunk holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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.

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.
ValueLocationComfort
5.0 out of 5 average rating, 105 reviews
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
LocationFamilyCheckout
4.99 out of 5 average rating, 70 reviews
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.
FamilyLocationKitchen
4.97 out of 5 average rating, 34 reviews
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.
LocationFamilyPool
4.93 out of 5 average rating, 213 reviews
"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
FamilyValueDecor
4.96 out of 5 average rating, 178 reviews
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
FamilyLocationAccuracy
4.9 out of 5 average rating, 119 reviews
Beach House w/ Heated Pool · Fire Pit · Kennebunk
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 Heated 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!
LocationFamilyComfort
4.83 out of 5 average rating, 180 reviews
Newly designed one-bedroom condo- heart of OGT
The newly furnished condo is located right in the center of everything that beautiful Ogunquit has to offer. Just a five minute walk to the beach and even closer to Ogunquit's landmark restaurants and bars, this is the most desirable location to stay in Ogunquit. Enjoy free on-site parking, a BBQ and on-site pool access. I am an airbnb super-host and an artist, whose first dance gig was at the Ogunquit Playhouse just up the street. I appreciate your rental as a way to support local artists.
LocationFamilyWalkability
4.97 out of 5 average rating, 108 reviews
Lovely Beach house in GRB - Heated pool!
Goose Rocks Beach Retreat | Heated Saltwater Pool & Ocean Views Just steps from beautiful Goose Rocks Beach, this classic coastal retreat offers the perfect setting for a memorable Maine getaway. Designed for families and groups, the home features a bright open-concept living space, a large deck with ocean views, and a heated saltwater pool (seasonal, typically May-Oct weather permitting). Enjoy easy beach access, plenty of room to gather, and all the comforts needed for a relaxing stay!
ValueFamilyOutdoor spaces
4.98 out of 5 average rating, 58 reviews
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.
LocationFamilyWalkability
5.0 out of 5 average rating, 144 reviews
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.
ValueLocationGetting around
4.96 out of 5 average rating, 158 reviews
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!
ValueLocationView
4.96 out of 5 average rating, 131 reviewsPopular amenities for Kennebunk rentals with a pool
House rentals with a pool

Sanctum by the Lake
FamilyValueLong stay
4.93 out of 5 average rating, 284 reviews
Faith Lane with community pool
FamilyLocationCheck-in
4.96 out of 5 average rating, 123 reviews
Designers Dream Home with Pool!
FamilyLocationAccuracy
5.0 out of 5 average rating, 14 reviews
Maritime Meadows – Charming Resort-Style Home!
FamilyLocationAmenities
5.0 out of 5 average rating, 21 reviews
Peaceful Cape Porpoise Retreat (House Only)
FamilyValueBackyard
4.83 out of 5 average rating, 12 reviews
2BR, Sea & Relax w/ Wells Reserve View
FamilyLocationCheckout
4.99 out of 5 average rating, 85 reviews
The Hurkle Durkle House
FamilyLocationSleep quality
5.0 out of 5 average rating, 36 reviews
Fantastic Kittery Home with Pool
LocationFamilyWalkability
4.96 out of 5 average rating, 69 reviewsCondo rentals with a pool

Two-Bedroom Condo on the Wells/Ogunquit town-line
LocationFamilyQuiet
4.86 out of 5 average rating, 228 reviews
Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6
ValueLocationLayout
4.93 out of 5 average rating, 128 reviews
Cozy, clean, 2nd floor condo in Conway, NH!
LocationValueAir conditioning
4.96 out of 5 average rating, 134 reviews
3BR, 2BA condo in No. Conway, Close to everything!
LocationFamilyHeating
4.98 out of 5 average rating, 199 reviews
The Gibson Building 3BR
LocationFamilyCheck-in
4.97 out of 5 average rating, 124 reviews
Elevate Your Adventure: Book Slope side Now!
ValueFamilyCleanliness
4.84 out of 5 average rating, 122 reviews
Spectacular Mountain Views, at Eagle Ridge !
FamilyLocationCleanliness
5.0 out of 5 average rating, 112 reviews
3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
ValueLocationTV
4.98 out of 5 average rating, 125 reviewsOther holiday rentals with a pool

Maine Coastal Village Getaway
FamilyValueLaundry
4.98 out of 5 average rating, 54 reviews
Ocean Beach Cottage Wells, ME
ValueLocationDecor
4.95 out of 5 average rating, 75 reviews
Paradise Found Minutes from Ogunquit | Heated Pool
ValueLocationView
5.0 out of 5 average rating, 94 reviews
Walk to Wells Beach | Pool | Hot Tub
ValueFamilyAccuracy
4.93 out of 5 average rating, 56 reviews
Old Falls Retreat-4BR w Gorgeous River View & Pool
LocationValueLayout
4.82 out of 5 average rating, 22 reviews
The Lodge at Hidden Pines
LocationFamilyOutdoor spaces
4.97 out of 5 average rating, 59 reviews
Super cute one bedroom with hot tub and pool.
FamilyValuePool
4.98 out of 5 average rating, 91 reviews
Stunning Beach House with an in-ground pool!
FamilyLocationComfort
4.67 out of 5 average rating, 24 reviewsWhen is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $419 NZD | $519 NZD | $655 NZD | $435 NZD | $384 NZD | $382 NZD | $447 NZD | $491 NZD | $318 NZD | $318 NZD | $382 NZD | $382 NZD |
| 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 |
Destinations to explore
- Condo rentals Kennebunk
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- Rentals with pools York County
- Rentals with pools Maine
- Rentals with pools United States
- Sebago Lake
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- North Hampton Beach
- Scarborough Beach
- Cape Neddick Beach
- Footbridge Beach
- Crane Beach
- Jenness Beach
- Hills Beach
- Gooch's Beach
- East End Beach
- Fortunes Rocks Beach
- Salisbury Beach
- Wallis Sands Beach
- Pleasant Mountain Ski Area
- Gunstock Mountain Resort





