
Vacation rentals with a pool in Kennebunkport
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Kennebunkport

Total vacation rentals
Explore 30 vacation rentals in Kennebunkport

Nightly prices starting at
Kennebunkport vacation rentals start at ﺩ.ﺇ 588 per night before taxes and fees

Verified guest reviews
Over 340 verified reviews to help you choose

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

Wi-Fi availability
30 of Kennebunkport vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kennebunkport rentals

4.8 Average rating
Kennebunkport stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Kennebunkport
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

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.

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 · 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 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.

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

Newly Renovated Studio Downtown!
The newly-renovated, 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 artist, whose first professional gig was at the Ogunquit Playhouse just up the street, and appreciate your rental as a way to support local artists.

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

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!

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.

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 Kennebunkport rentals with a pool
House rentals with a pool

5 Bedroom Home Pool & Hot Tub

Faith Lane with community pool

Beach Plum-Elegant Coastal Escape

Unique Church Accommodation • Sebago Lake • Pool • Fire Pit

*Close to Beach*POOL* *5 Star Reviews*

2BR, Sea & Relax w/ Wells Reserve View

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

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

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Just Beachy New Rental

Lovely Ogunquit Studio, Pools, Walk to Everything!

LUXURY OCEANFRONT CONDO Best Location on the beach

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

Condo in Old Orchard Beach

Our Happy Place!

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

Four Story Townhouse With Ocean View 55

Freshly Renovated, Family-Friendly Coastal Cottage

Crosswinds Cottage 17

Steps to Wells & views of Rachel Carson Preserve

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

Studio Condo, Deck, Pool, Hot Tub, Playground

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

Paradise Found Minutes from Ogunquit | Heated Pool
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- Sebago Lake
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- North Hampton Beach
- Scarborough Beach
- Footbridge Beach
- Crane Beach
- Cape Neddick Beach
- Jenness Beach
- East End Beach
- Gooch's Beach
- Salisbury Beach
- Hills Beach
- Fortunes Rocks Beach
- Gunstock Mountain Resort
- King Pine Ski Area
- Wallis Sands Beach
- Popham Beach State Park





