Vacation rentals with a pool in Kennebunkport

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Top-rated rentals with a pool in Kennebunkport

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Guest favorite

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

4.95 out of 5 average rating, 632 reviews

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.

Superhost

A campfire burns brightly near the shoreline, with flames reflecting off the calm water. Adirondack chairs are positioned nearby, providing a serene view of the sunset over the lake, framed by trees and a rocky edge.

Home in Barnstead

4.87 out of 5 average rating, 126 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

Leave the day-to-day behind & enjoy the beautiful scenery, the wildlife and all the fun of a lake-front vacation! There's so much to enjoy: from a nice cup o' Joe sitting on the deck facing the lake, to swimming, kayaking, paddle-boarding, to enjoying sunsets while making s-mores for the kids at the campfire, to grilling juicy burgers with family and friends, plus ping-pong, darts, board games, streaming your favorite shows near a cozy fireplace. And so much more in the awesome NH Lakes Region!

Guest favorite

A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.

Apartment in Cape Elizabeth

4.87 out of 5 average rating, 563 reviews

Portland & Beach & Lighthouses! Romantic! Lovely

Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

Guest favorite

An expansive in-ground pool is surrounded by a spacious wooden deck, featuring comfortable lounge chairs. The house, with gray siding, is visible in the background, flanked by trees that provide privacy. Soft clouds pass overhead, contributing to a tranquil outdoor setting.

Home in Kennebunk

4.84 out of 5 average rating, 149 reviews

Kennebunk/Kennebunkport Beach House w/Pool!

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!

Top guest favorite

A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.

Apartment in Back Cove

5 out of 5 average rating, 73 reviews

Luxe Eco Studio near Back Cove

2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

Top guest favorite

Place to stay in Shapleigh

5 out of 5 average rating, 81 reviews

Historic Schoolhouse c1866 / Pets OK / Hot tub

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 and tennis court.

Guest favorite

A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.

Cottage in Wells

4.94 out of 5 average rating, 153 reviews

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.

Guest favorite

A clear view of a heated pool surrounded by a spacious deck, featuring white lounge chairs and vibrant blue poolside furniture. Tall trees provide shade nearby, and a fence surrounds the pool area, ensuring privacy and safety. The open area beyond the pool includes green grass and additional cottage units.

Cottage in York

4.97 out of 5 average rating, 146 reviews

Tiny house living close to Ogunquit center!

The cottage was completely remodeled in spring of 2018. It is one of 21 cottages built in 1920. The back of the cottage is a rolling meadow and woods. It feels secluded, yet you are only a mile from all the wonderful happenings in Downtown Ogunquit, Perkins Cove & Ogunquit beach. Come enjoy the beach, shopping and amazing restaurants. Check out the Nubble Lighthouse, shop the outlets in Kittery or walk around Portsmouth NH. This tiny cabin is convenient to so much. Come rejuvenate!

Top guest favorite

A refreshing seasonal pool displays sparkling blue water, surrounded by a spacious deck and lawns. A colorful striped pool float rests on the surface, while the historic Chapman House is visible in the background, framed by tall trees and sunlight filtering through.

Guesthouse in Rosemont

4.96 out of 5 average rating, 528 reviews

Romantic Bungalow w/ Pool, 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

Superhost

An inviting entrance is framed by a white picket fence and an archway adorned with greenery. Stone pathways lead to the double front doors of the charming home, complemented by lush landscaping and mature trees, creating a welcoming coastal atmosphere.

Condo in Kennebunkport

5 out of 5 average rating, 4 reviews

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.

Guest favorite

A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.

Home in Kennebunkport

4.97 out of 5 average rating, 32 reviews

Lovely Beach house in GRB - Heated pool!

A classic Kennebunk beach house, just a few steps from Goose Rock Beach! The true definition of open concept is on the second floor with kitchen, dining and living areas. Two sliding doors lead to a huge deck with oceanviews for entertaining. Enjoy the heated saltwater swimming pool, open seasonally (scheduled to close in October 2024 and reopen in May 2025 - subject to change depending on weather conditions).

Top guest favorite

Home in Old Orchard Beach

4.96 out of 5 average rating, 112 reviews

OOB Oasis - 5BR private Retreat w/ Pool

Welcome to our stunning home, and your private oasis in Old Orchard Beach! Inside, this custom-built home features 3 suites (each with its own private bathroom), a gourmet kitchen w/ high-end appliances, a sprawling open floor plan, and ample parking for large groups. Outside, you'll find a large fenced backyard, deck with BBQ grill, and in-ground pool perfect for cooling off on hot summer days.