Vacation rentals with a pool in Kennebunk

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kennebunk

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Guest favorite

Loft in Falmouth

4.95 out of 5 average rating, 545 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.

Nov 22 – 29

G$49,729 GYD per night

Guest favorite

Home in Kennebunk

4.81 out of 5 average rating, 114 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!

Feb 22 – Mar 1

G$117,782 GYD per night

Guest favorite

Condo in Bartlett

4.88 out of 5 average rating, 101 reviews

Cozy 1 BR Resort Condo; Fireplace; Amazing views

Located at one of Mount Washington Valley's Premier resorts, this 1 BR condo is the perfect destination for a family weekend or romantic getaway. Enjoy all that MWV has to offer and then return home to a cozy space to relax and unwind. Access to full resort amenities is available (add fee), incl. pools, rec room, trails and more. Minutes from Storyland and Jackson Village. Just a short drive to numerous downhill and x-country skiing venues as well as tax free shopping and dining in North Conway.

Mar 12 – 19

G$32,058 GYD per night

Guest favorite

Tiny home in Harrison

4.9 out of 5 average rating, 280 reviews

MILLION$ views, HOT TUB, Crooked RIVER, 14 acres

Pets Welcome. Hot tub with a EPIC view. Escape to complete privacy on 14 acres of stunning riverfront property on the Crooked River. This A-frame cabin offers plenty of outdoor activities, a pond, riverfront access, and trails for picking berries. Relax by the river, go camping, or spot wildlife from the front porch or hot tub. The home is clean, modern, and tidy with a new bathroom and furniture. It also has air conditioning and fast wifi. Don't miss out on this unique getaway opportunity.

Feb 12 – 19

G$100,312 GYD per night

Guest favorite

Cottage in Wells

4.93 out of 5 average rating, 135 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.

Sep 11 – 18

G$64,673 GYD per night

Guest favorite

Condo in Intervale

4.88 out of 5 average rating, 123 reviews

Top Floor! Incredible views/ close to town/hiking

Newly renovated cozy 1 king bedroom /1 bath condo less than 2 miles from the center of North Conway! 10 minute drive to Attitash and Cranmore ski resorts. Enjoy stunning views of Mount Washington Valley from your private deck. Relax by the cozy fireplace as you watch the sun set over the mountains. Head into town to enjoy local restaurants, shops, and breweries. Hiking trails/ cross country ski trails and downhill skiing just a short distance away. Living room has a queen sleeper sofa

Mar 3 – 10

G$27,861 GYD per night

Guest favorite

Cottage in York

4.98 out of 5 average rating, 118 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!

May 15 – 22

G$42,647 GYD per night

Guest favorite

Home in Scarborough

4.98 out of 5 average rating, 229 reviews

Swim spa under the starry night pool/hot tub/sauna

Dreams do come true! Stay here and experience the pleasure of your own private Solar powered and Eco friendly spa resort getaway in Maine! Experience your own private spa in a four season sunroom with a heated indoor fitness pool of 90 degrees and a hot tub at 101 degrees. Boost your immune system with hydrotherapy. With an outdoor sauna steps away, and a fire pit this is truly a treat. We are close to beaches, lighthouses and Portland's Old Port just minutes away.

Jan 31 – Feb 7

G$80,189 GYD per night

Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 394 reviews

Romantic Bungalow with Hot Tub & Parking

The Bungalow is a private, luxury en-suite 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

Aug 29 – Sep 5

G$56,282 GYD per night

Guest favorite

Guest suite in Saco

4.99 out of 5 average rating, 104 reviews

Secret Garden Suite

This completely remodeled private suite is in a quiet neighborhood just footsteps from Marston's Marina. We are a bikeable 1.5 miles to the Saco beaches and an easy 5 minute drive to the bustle of Old Orchard Beach, or you can avoid it completely. This apartment with kitchenette and bath is designed for two, but can also accommodate new parents with a baby or toddler. Relax on the balcony overlooking the gardens and heated pool or take a dip to cool off!

Jul 18 – 25

G$39,886 GYD per night

Guest favorite

Condo in Gilford

4.9 out of 5 average rating, 126 reviews

Lake or Ski Condo, close to Gunstock and the Lake

Location and Amenities! 10 min from Gunstock, couple hundred yards from the Lake, 50 yards from Gilford concert stage and the back entrance. Access to Barefoot Beach, Lake Winnipesaukee, outdoor pool, tennis courts, grill high speed WiFi and more. 1 Bedroom studio and a pull out couch, sleeps 4 comfortably. Large bathroom and shower. Ski 10 min away or ice fish 150 yards away. Laconia Bike week only Minutes away! 1 Free parking spot.

Sep 29 – Oct 6

G$41,625 GYD per night

Guest favorite

Condo in Bartlett

4.94 out of 5 average rating, 181 reviews

An Amazing Mountain Getaway!

Come and relax at our Nordic Village vacation condo! The 2-bedroom, 2-bath end unit features 2 stories with a spiral staircase, fireplace and a deck! Nordic Village amenities include pools, hot tubs, a sauna and more when you're not skiing at Attitash, Cranmore, Wildcat or Black Mountain! With Story Land 1 mile away, idyllic North Conway and all that's best of White Mountain National Forest within minutes, this getaway has it all!

Nov 12 – 19

G$37,014 GYD per night