Vacation rentals with a pool in Kittery

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Top-rated rentals with a pool in Kittery

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

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Top 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, 662 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.

Top guest favorite
A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.
Home in Derry
4.93 out of 5 average rating, 233 reviews

Sanctum by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Top guest favorite
A living room displays a gray tufted sofa adorned with decorative pillows and a green accent pillow. A round wooden tray holds two white candles on a leather ottoman. Two elegant lamps provide soft lighting, complemented by large windows draped with sheer curtains.
Apartment in Rosemont
4.97 out of 5 average rating, 463 reviews

Apt in Victorian Mansion w/ Hot Tub & Parking

Mixing contemporary styling with old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our pool or relax by the fire pit, our half-acre yard offers a tranquil space for all. The apartment has a chef's kitchen, dining, and living room with gas fireplace. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

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.
Condo in Gilford
4.9 out of 5 average rating, 248 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 favorite
A charming red schoolhouse, dating back to 1866, is surrounded by tall trees and a well-kept grassy area. The structure features white trim, large entrance doors, and a bell tower, evoking a sense of history and nostalgia.
Place to stay in Shapleigh
5 out of 5 average rating, 108 reviews

Romantic New England Historic Schoolhouse c1866

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.

Top guest favorite
A welcoming entryway is framed by flowering shrubs and greenery. A small brick path leads to a light-colored door, accented by decorative lanterns. Potted plants add color, while a charming garden statue is positioned on the ground, contributing to the inviting exterior.
Guesthouse in Belmont
4.98 out of 5 average rating, 246 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

Top 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
4.95 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.

Top guest favorite
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!

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!

Guest favorite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish
4.92 out of 5 average rating, 116 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.

Guest favorite
A cozy loft area features a comfortable seating arrangement with a plush chaise lounge, inviting relaxation. Natural light filters through a skylight, highlighting warm wooden beams and connecting to a private deck that offers scenic mountain views.
Cabin in Campton
4.84 out of 5 average rating, 135 reviews

The Golden Eagle - Mountain Lodge

Stunning cabin in the heart of the White Mountains of NH. Cozy up in this beautiful luxury lodge which offers great views of the mountains and privacy throughout your stay. This gorgeous cabin boasts three bedrooms, three private decks, a loft for studying or relaxing with a dedicated work space, and a private outdoor area for grilling or having a campfire. Elegantly placed on the side of Campton Mountain the home is just minutes from I-93 and Waterville Valley.

Top guest favorite
A spacious living area features a stone fireplace, surrounded by windows offering views of the snowy landscape. Natural wood accents and warm tones create a cozy environment, while a comfortable chair and woolen blanket invite relaxation.
Chalet in Campton
4.9 out of 5 average rating, 406 reviews

Mountain cabin with views, privacy, and more.

Cabin in the woods with amazing mountain views. Situated on 2.5 acres and surrounded on 3 sides with 30 additional steep wooded acres; peace and privacy. NOTE: winter driving will require snow tires or 4wheel drive as the house is on an incline road. Skiing, Snowboarding: - 25 minute drive to Loon Mountain - 25 minute drive to Waterville Valley (discounted lift tickets available) Cabin professionally cleaned between stays w/extra attn on high touch areas.

Guest favorite
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.

Popular amenities for Kittery rentals with a pool

When is the best time to visit Kittery?

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Avg. price€ 103€ 99€ 87€ 100€ 140€ 163€ 220€ 302€ 198€ 129€ 135€ 117
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Quick stats about vacation rentals with a pool in Kittery

  • Total vacation rentals

    Explore 20 vacation rentals in Kittery

  • Nightly prices starting at

    Kittery vacation rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 1,340 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Kittery vacation rentals include wi-fi 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!

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