
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.

Loft Apartment on Tree-Lined Street in Falmouth
Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

"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.

Apt in Victorian Mansion w/ Hot Tub & Parking
Mixing contemporary styling with old-world charm, the Apartment in the Registered Chapman House offers a relaxing private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by the fire pit, our half-acre yard offers a tranquil experience. The apartment has a chef's kitchen, dining, and living room with gas fp. NB., use of the living room bed may incur a charge. Please ask There is a L2 EV charging outlet. #allarewelcome

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.

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.

Paradise Found Minutes from Ogunquit | Heated Pool
Your Year-Round Oasis in Seaglass Village close to Ogunquit Maine! Nestled within a picturesque resort community in the heart of Maine, "Paradise Found" is more than just a cottage; it's your ultimate year round retreat. Immerse yourself in comfort and convenience with newly updated furniture, a modern kitchen featuring granite countertops, central AC and heating throughout the home, an in unit washer and dryer, wifi, cable and a delightful golf cart to explore this coastal haven.

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

Heated Pool & Ocean Access | 15 Mins to Portland

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

Beach Dreams Cottage w/ Central A/C

Our Beach House Getaway

Cozy Beach Cottage - Wells, ME

Cozy Maine Church Retreat Near Portland • Fire Pit

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

Walkable Downtown North Conway w private hot tub!
Condo rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Ski Condo on Cranmore Mountain-Pool and Hot tub!

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

Steps from Beach | Pool | Parking | Large Deck

Condo in Old Orchard Beach

Centrally located Ocean Towers condo in Ogunquit

Cozy, clean, 2nd floor condo in Conway, NH!

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
Other holiday rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Home Near Beaches & Fun

1 bedroom with pool, walk to the beach.

Freshly Renovated, Family-Friendly Coastal Cottage

Pool and walking distance to beaches! Amenities!

"Secret Summer" Savings

Beautiful 2 bedrm cottage in Beach Dreams complex

Heron's Hide-Away

Cottage 2 @ Coast Village Inn
When is the best time to visit Kennebunk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $386 NZD | $286 NZD | $386 NZD | $288 NZD | $296 NZD | $342 NZD | $431 NZD | $473 NZD | $307 NZD | $307 NZD | $369 NZD | $369 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 |
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 $84 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
180 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!
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