
Holiday 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.

"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 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Luxury Oceanview 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

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.

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym
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, gym and tennis court.

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.

Cozy and private guest cottage near the beach
Spend a care-free week near the beach! Everything you need is right here in this cozy seasonal cottage within walking distance to the ocean, great ice cream, and centrally located to all the antique shops, restaurants, and site seeing you can imagine. And if you get tired of the beach, hang out in our fenced in yard with an in-ground pool and fire pit! There is a 2 adult limit, and there are NO pets allowed. Free parking, wifi, cable TV Please note: Cottage is not handicap accessible

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.

Cottage in Wells Maine
Welcome to “Sea-clusion”, Come and enjoy a weekend or the week in this newly updated attached studio. Sleeps up to four with a king size bed and a comfortable full size futon. The kitchen is fully equipped to cook your favorite meal or you may choose to enjoy one of the several options within walking distance. Relax after a day at the beach on the large enclosed porch or cook on your grill right outside the front door. Kayaks are right at the marina. We hope you enjoy your stay!

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!

Romantic Bungalow w/ Hot Tub & Parking
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

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.

Stylish Designer Retreat on Langsford with Pool
KPort Concierge warmly invites you to The Langsford, your ideal coastal retreat in Cape Porpoise. Immerse yourself in the quintessential coastal Maine experience with this luxury one-bedroom property in Cape Porpoise, a historic lobster village that beautifully blends history with modern charm. This upscale townhome features a stunning in-ground pool, fire pit, and grill, all set amidst gorgeous landscaping, providing an idyllic setting for relaxation.
Popular amenities for Kennebunk rentals with a pool
House rentals with a pool

Townhouse near Gunstock, Bank of NH Pav, Ellacoya

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

Beach Dreams Cottage w/ Central A/C

Sanctum by the Lake

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

There's No Place Like Home

Bear Brook House

River Access|Gas stove|Min to N. Conway, Attitash
Apartment rentals with a pool

Attitash Studio | 5min to Storyland| Pools

Ski Condo on Cranmore Mountain-Pool and Hot tub!

AttitashResort! 1-flr, studio, secure check-in

KimBills’ on the Saco

Elevate Your Adventure: Book Slope side Now!

An Amazing Mountain Getaway!

Peaceful Condo Near Storyland & Attitash Skiing

Mountain Views • Fireplace • Hot Tub • Pool Escape
Other holiday rentals with a pool

1 bedroom with pool, walk to the beach.

Freshly Renovated, Family-Friendly Coastal Cottage

Everything's "Well Ashore"- 1 mile to Wells Beach!

Cozy Beach Cottage - Wells, ME

Centrally located Ocean Towers condo in Ogunquit

Kennebunk's Charming Beach Home

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Seaside Condo w/stunning views, 2 Queen sized beds
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £168 | £125 | £168 | £126 | £129 | £149 | £188 | £206 | £134 | £134 | £161 | £161 |
| 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 holiday rentals with a pool in Kennebunk

Total holiday rentals
Explore 180 holiday rentals in Kennebunk

Nightly prices starting at
Kennebunk holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 4,150 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
60 properties have a dedicated workspace

Wifi availability
180 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Rentals with beach access Kennebunk
- Apartment rentals Kennebunk
- Rentals with breakfast Kennebunk
- Rentals with a kayak Kennebunk
- Rentals with outdoor seating Kennebunk
- Waterfront rentals Kennebunk
- Flat rentals Kennebunk
- Cottage rentals Kennebunk
- Pet-friendly rentals Kennebunk
- Private suite rentals Kennebunk
- Rentals with an EV charger Kennebunk
- Rentals with a firepit Kennebunk
- Beachfront rentals Kennebunk
- Rentals with a fireplace Kennebunk
- House rentals Kennebunk
- Rentals with a washing machine and dryer Kennebunk
- Family-friendly rentals Kennebunk
- Rentals with a patio Kennebunk
- Hotel rooms Kennebunk
- Cabin rentals Kennebunk
- Fitness-friendly rentals Kennebunk
- Rentals with a hot tub Kennebunk
- Guest house rentals Kennebunk
- Rentals with pools York County
- Rentals with pools Maine
- Rentals with pools United States
- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Weirs Beach
- Crane Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- North Hampton Beach
- King Pine Ski Area
- East End Beach
- Willard Beach
- Short Sands Beach
- Gooch's Beach
- Cape Neddick Beach
- Funtown Splashtown USA
- Gunstock Mountain Resort
- Bear Brook State Park
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Palace Playland




