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, 397 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)

Superhost
An aerial view captures a serene lakeside setting, featuring a sandy beach lined with lounge chairs. Several boats are docked along the shore, while trees and buildings provide a natural backdrop, creating an inviting space for outdoor relaxation and activities.
Apartment in Gilford
4.9 out of 5 average rating, 249 reviews

Great Condo near Gunstock, Lake Access & Concerts

Location and Amenities! We are the closest condo to the concert path on Misty Harbor!! 10 min from Gunstock, couple hundred yards from the Lake, 50 yards from Gilford concert stage 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

Top guest favourite
Place to stay in Shapleigh
5 out of 5 average rating, 113 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
Flat in Charlestown
4.91 out of 5 average rating, 142 reviews

Lux 2BR Apt w/ Pool and Gym

Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

Top guest favourite
A cozy hotel room features a King bed adorned with a patterned blanket and wall-mounted artwork. A wooden bench sits at the foot of the bed, and a chair is positioned near the window, which offers natural light and a view of the surrounding landscape.
Apartment in Lincoln
4.93 out of 5 average rating, 108 reviews

Hotel Style room w/pool, stunning Mountain view

Stylishly renovated Hotel room at the Lodge at Lincoln Station resort. Sleeps 2. Featuring King bed, Microwave and coffee maker. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

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
4.84 out of 5 average rating, 224 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, 389 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
A bright sitting room features large windows that invite natural light and offer views of the harbor. A round table with two chairs occupies the space, alongside a built-in seating area with cushions. A door leads to an outdoor deck, enhancing indoor-outdoor connectivity.
Guest suite in West End
4.99 out of 5 average rating, 361 reviews

Sunny West End Guest Suite w/Harbor Views and Pool

Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

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, 129 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
The living area features a cozy seating arrangement with a stylish coffee table and a decorative wall adorned with snowshoes. Large windows provide a scenic view of the surrounding fall foliage and mountains, while a television is mounted above a warm fireplace.
Flat in Lincoln
4.92 out of 5 average rating, 167 reviews

Breathtaking View, <3mins to Loon, NEW Renovation!

Welcome to our cozy, modern and NEW renovated 2-bedroom property located in the beautiful town of Lincoln, New Hampshire. With comfortable sleeping arrangements for up to 4 guests and 1 bathroom, our property offers a convenient and comfortable base for exploring the stunning White Mountains region. Step outside and discover a world of adventure, from hiking to skiing, water sports to sightseeing.

Popular amenities for Kittery rentals with a pool

When is the best time to visit Kittery?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£90£86£76£88£122£142£191£263£173£141£79£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 £52 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