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, 617 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 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, 553 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

4.83 out of 5 average rating, 144 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!

Guest favorite

Home in North Deering

4.95 out of 5 average rating, 127 reviews

"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 eateries and breweries. 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

Guest favorite

A cozy bedroom features a spacious bed dressed in fresh white linens with a nautical-themed throw blanket. Two framed black-and-white photographs are displayed above the bed. Soft lighting is provided by two bedside lamps, creating a calm, restful environment.

Apartment in Wells

5 out of 5 average rating, 8 reviews

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

Welcome to 'Well Ashore', a charming 1-bedroom, 1-bathroom 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, plentiful benches, and an easy access to downtown Ogunquit.

Guest favorite

The exterior of a charming three-story building is visible, adorned with a warm stucco finish. A seasonal pool in the foreground reflects the structure. Various patio seating options and an umbrella area create an inviting outdoor space, complemented by lush greenery in the surrounding garden.

Apartment in Rosemont

4.98 out of 5 average rating, 254 reviews

Maine Hacienda w/hot tub & seasonal pool

Our renovated suite at the foot of Deering Highlands is a 10 minute drive to downtown Portland. A cozy, quiet, modern space with a maritime edge. A short walk to Woodford’s corner and Forest Ave - home to many restaurants & coffee shops. The space includes a seasonal pool and year-round hot tub. Ideal for singles, couples or couples with one or two small children. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.

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, 148 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, 137 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!

Superhost

An outdoor heated pool is framed by lounge chairs, providing a space for relaxation. The pool reflects the two-story building behind, with large windows visible. Umbrellas offer shade on sunny days, and well-maintained grass surrounds the pool area.

Condo in Wells

4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

Our two-bedroom units are located on the first, second or third floor in our all-stair property. All of our two-bedroom units have two bedrooms, with a varying number of beds, two bathrooms, full kitchen, living room, dining room and patio/balcony. They have a washer and dryer too! All kitchens come equipped with standard dishes, baking and cooking supplies, as well as full size appliances! Best for larger families to spread out! Room requests are accepted but not guaranteed.

Guest favorite

A sparkling outdoor pool is surrounded by lounge chairs on a sunlit patio. Lush green trees provide shade in the background, and blue umbrellas are positioned nearby. Clear water reflects the sunlight, creating a refreshing atmosphere.

Townhouse in Goose Rocks Beach

4.92 out of 5 average rating, 26 reviews

Goose Rocks Getaway

This cozy, beach-themed condo has everything you need for an amazing trip to southern Maine! Ground-floor condo (2 br, 1.5 ba, full kitchen) only 1 mi. from beautiful Goose Rocks beach and 3.5 mil. from Dock Square in KPort is great for a family vacation, romantic couple’s getaway, or trip with friends! Amenities: outdoor & indoor pool, hot tub, exercise room, outdoor grills & picnic tables, and sports courts. All beach necessities (towels,chairs, umbrellas, toys) included!

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, 512 reviews

Romantic Bungalow with Hot Tub, Pool & 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

Guest favorite

A swimming pool is framed by a concrete deck, with lounge chairs positioned nearby. Colorful chairs are set along the fence, which provides a boundary. A serene evening sky with soft hues enhances the tranquil setting.

Guest suite in Standish

4.93 out of 5 average rating, 104 reviews

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.