Holiday 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 favourite
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, 667 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
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, 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, 109 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.

Top Guest favourite
Home in Campton
5 out of 5 average rating, 109 reviews

Stylish Mtn Home-Ski/ Pools/ Hot Tubs & Fire Pit

Imagine waking up in a luxurious 3-bedroom retreat in Waterville Estates, surrounded by the White Mountains. Spend your day exploring nearby hiking trails, swimming in pools, or relaxing in the hot tub and sauna. Enjoy a BBQ on the gas grill, play cornhole in the backyard, and end your day stargazing by the stone fire pit. With modern, high-end finishes and rustic charm, plus access to a ski lodge, game room, restaurant, and Community Center just a 2-minute walk away, this property has it all!

Top Guest favourite
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, 467 reviews

Apt in Victorian Mansion w/ Hot Tub & Parking

Mixing contemporary styling with old-world charm, the Apartment in the 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 seasonal pool, or relax by the fire pit, our half-acre yard offers a tranquil experience. The apartment has a chef's kitchen, dining, and living room with gas fp. NB., use of the living room bed may incur a charge. Please ask There is a L2 EV charging outlet. #allarewelcome

Top Guest favourite
A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.
Home in Kittery
4.97 out of 5 average rating, 58 reviews

Fantastic Kittery Home with Pool

Modern New Englander boasting a large, private backyard with pool (seasonal, from May to Oct, approx). Our comfortable, 3-bedroom home is a commuter's dream. Working from home? Use our separate dedicated office space with 1 gig WiFi. Playing hooky? So many options! Walk or bike to the fabulous eateries, shopping or breweries our area has to offer! Enjoy our pool or take a short drive to the beach! (Please note, our pool is normally unheated. For an additional $40 a day we'll heat it!)

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
The living area features a stone fireplace as a focal point, accompanied by a comfortable dark sofa and armchair. A wooden coffee table is centered on a patterned rug. A flat-screen TV is mounted on the wall, while decorative accents like a wall-mounted ladder and artwork complement the space.
Condo in Campton
4.9 out of 5 average rating, 312 reviews

The Alpine Oasis

Escape, relax and enjoy White Mountain views and postcard quality sunsets from our cozy mountainside condo. Bordering the White Mountain National forest with over twelve hundred miles of hiking trails. We are minutes from New Hampshire's world famous outdoor playground. Ski, snowboard or tube at one of three ski areas within a 25 minute drive; Waterville Valley, Loon and Tenney. We humbly invite you to come and stay, unwind and make friends with yourself again.

Guest favourite
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, 410 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 - 25 minute drive to Tenney Mountain Resort Cabin professionally cleaned between stays w/extra attn on high touch areas.

Guest favourite
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 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!

Popular amenities for Kittery rentals with a pool

When is the best time to visit Kittery?

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Avg. price$204 NZD$195 NZD$172 NZD$199 NZD$278 NZD$321 NZD$434 NZD$597 NZD$392 NZD$256 NZD$267 NZD$232 NZD
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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 $118 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Wi-Fi availability

    20 of Kittery holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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