Holiday rentals with a pool in Kittery

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kittery

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Flat in Waltham
4.97 out of 5 average rating, 393 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Top guest favourite
Place to stay in Shapleigh
5 out of 5 average rating, 112 reviews

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.

Guest favourite
A cozy living area features a dark blue sofa adorned with decorative pillows. A light-colored coffee table sits in front, while natural light enters through a large window framed by light curtains. A small cart and lamp complement the space, enhancing the inviting atmosphere.
Apartment in Bartlett
4.91 out of 5 average rating, 181 reviews

Cozy Condo at Attitash!

Enjoy activities & beautiful scenery offered at Attitash Mountain Village, in the White Mountains! This cozy one bedroom, 2nd floor condo sleeps four, and includes a completely renovated kitchen/living area and bathroom! You will be just steps away from a beautiful pool pavilion, tennis courts, playgrounds, the Saco River Beach, hot tubs, fire pits, an arcade, and a fitness center. Nestled among all the summer attractions of the area- 10 minutes to Story Land! Always something fun to do!

Top guest favourite
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
4.95 out of 5 average rating, 166 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 favourite
A spacious studio apartment is presented, featuring a full bed with soft linens and decorative pillows. Natural light fills the room through large windows, which are dressed with elegant curtains. A modern seating area includes a sleek black sofa and an armchair, creating a comfortable relaxation space.
Flat in Beachmont
4.85 out of 5 average rating, 221 reviews

Stylish and Cozy at Revere Beach

Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Top guest favourite
Apartment in North Woodstock
4.92 out of 5 average rating, 386 reviews

Luxury Suite Jacuzzi Pool White Mtns. River Front

Amazing location in heart the White Mountains Clubhouse, Beach, Lake, Pool, Hot Tub, River, Tennis, Racquetball, Gym, Sauna, Wally-ball, Game rooms, Grills, nature trails on site, Ice skating, and more. Shuttle to Loon River View Best Amenities In the Area Perfect for Romantic Retreat/Skiing/ Hiking. Jacuzzi tub, spa shower and zen design in unit! Close to-Scenic Kancamagus, hikes, Loon, waterpark, and Ice Castles. Walk to Cafe Lafayette Dinner Train & Woodstock Inn Brewery.

Top guest favourite
An exterior view of The Bungalow showcases its charming design with a well-maintained greenish-yellow facade. Two black doors provide access, while vibrant flowering plants grow nearby. A small patio set with chairs and a table is prominently positioned in front, inviting outdoor relaxation.
Guest house in Rosemont
4.97 out of 5 average rating, 575 reviews

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

Top guest favourite
Apartment in Lincoln
4.95 out of 5 average rating, 152 reviews

White Mountain Resort Pool/HotTub Shuttle to Loon

Perfect for a single or couple Luxurious but affordable Private but located inside a resort with top notch amenities Quiet & Clean Queen bed with sofa bed suitable for a child Updated / Modern Studio Condo directly on “ The Kanc” Main Street Lincoln Walking to restaurants, pubs and shops, easy access to The White Mountains - Lincoln NH Hiking skiing, zip-lining, ice castles, shopping, Clarks Trading Post, Cannon and Loon Mountain, Santa’s Village, and more

Guest favourite
A spacious living area features a comfortable sectional sofa with patterned upholstery, situated alongside large windows offering expansive views of the waterfront. Natural light floods the room, complemented by warm wooden accents on the ceiling and floor. A dining table for four is placed near the windows.
Cottage in Plum Island
4.92 out of 5 average rating, 127 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (open June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Top guest favourite
A charming cottage features light blue siding and white trim, complemented by a small porch with railing. Surrounding trees provide shade, while a picnic table and grill are positioned in the grassy yard. Stone landscaping offers a natural backdrop to the cottage.
Cottage in York
4.97 out of 5 average rating, 153 reviews

Tiny house living close to Ogunquit center!

This tiny house 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 favourite
Guest suite in Manchester
4.95 out of 5 average rating, 175 reviews

The Haven at Doherty Homestead

Our pricing is transparent; there are no cleaning fees or surprise costs. Looking for a cozy place to crash after adventuring about? One hour from Boston, the ocean or the mountains, we are 10 minutes from city life as well as local hiking spots. Prefer a restful respite? Our backyard is your oasis; firepit, meditation treehouse, hammocks and patio area complete with a dining table, outdoor TV and lounge furniture.

Top guest favourite
The open kitchen features modern stainless steel appliances, including a refrigerator and stove. A spacious island with Quartz countertops provides seating for four, complemented by white bar stools. The dining area is visible, showcasing a dining table set for six, with natural light flowing in from nearby windows.
Townhouse in North Conway
4.96 out of 5 average rating, 370 reviews

Family friendly + Mountain Views @amountainplace

Our Family-Friendly, Mountain View Townhouse is tucked away but just an 8 minute drive to downtown North Conway. Relax by the gas fireplace, soak in the views, cook in the updated kitchen, swim in the heated outdoor pool (open Memorial Day to Labor Day) or head out the backyard to find hiking trails. Great proximity to all the White Mountains has to offer. Don’t miss out!

Popular amenities for Kittery rentals with a pool

When is the best time to visit Kittery?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£89£85£75£86£121£140£189£260£171£139£78£70
Avg. temp-5°C-3°C1°C7°C13°C18°C21°C20°C16°C10°C4°C-1°C

Quick stats about holiday rentals with a pool in Kittery

  • Total holiday rentals

    Explore 20 holiday rentals in Kittery

  • Nightly prices starting at

    Kittery holiday rentals start at £51 per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Wifi availability

    20 of Kittery holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kittery rentals

  • 4.9 Average rating

    Kittery stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Kittery
  6. Rentals with pools