
Vacation rentals with a pool in Kittery
Find and book unique homes with a pool on Airbnb
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 ﺩ.ﺇ 331 per night before taxes and fees

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Over 1,470 verified reviews to help you choose

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!
Top-rated rentals with a pool in Kittery
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Sunset Waterfront Retreat | Private Beach, Pool &
Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

Portland & Beach & Lighthouses! Romantic! Lovely
Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only 10 min to downtown. Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by one of our fire pits, our half-acre yard offers a tranquil stay. The apartment boasts a newly renovated bathroom, radiant heated floors in both kitchen & bath, and a chef's kitchen. This grand apartment won't disappoint. L2 EV charging outlet on site #allarewelcome

Starfish Condo Wells Beach
Enjoy the amazing sunrise as well as marsh and ocean views from this spacious just renovated one and a half bedroom condo with queen bed and queen Murphy bed. Fully equipped kitchen with granite counter tops and stainless steel appliances. Updated full bath with tub. Located within walking distance to many local area restaurants. After a fun filled day on the beach relax by the salt water pool or in the hot tub. Shared gas grill, picnic area, playground and basketball hoop. Parking for one car

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

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.

Basecamp in the White mountains
This small cabin has been re-built with new pine paneled walls and ceiling, bunk beds, carpeting, electricity, a new Eco-outhouse!, solar shower and It is located at the edge of a field about 100 yards from our home. It is a perfect base camp for hikers 12 miles south of Franconia notch trail heads and Appalachian Trail crossing. The cabin is most often used by hikers who want a base camp near many of the most popular hiking trails near Franconia Notch. It is a peaceful and quiet place.

Luxury Retreat In Back Cove | 10 Min to Downtown
Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

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.

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
House rentals with a pool

Beach Getaway Minutes from the Ocean!

Fantastic Kittery Home with Pool

Faith Lane with community pool

Modern Mountain Retreat at Waterville Estates

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast

Spacious vacation unit in premium suburban town

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Charming Lake Comm Bungalow - EV charging/86” tv
Condo rentals with a pool

Luxury Studio White Mtns Jacuzzi Pool Pond River

The Alpine Oasis

Cozy Condo in the Valley

Serenity by the Sea

Million $ View of Lake Winni Flexible check in/out

Steps to Wells Beach + Pool | Coastal Retreat

Cozy, clean, 2nd floor condo in Conway, NH!

Cozy Family Retreat with Saco River Access
Other vacation rentals with a pool

Hampton Beach Bailey's Resort

Little Nubble Nook - Beach Condo

Designers Dream Home with Pool!

Paradise Found Minutes from Ogunquit | Heated Pool

Forest Lodge at Haskell Gove Farm

Headers’ Haven

2 BR house, close to Ogunquit, w/ AC + golf cart!

Ocean Beach Cottage Wells, ME
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 323 | ﺩ.ﺇ 353 | ﺩ.ﺇ 397 | ﺩ.ﺇ 433 | ﺩ.ﺇ 606 | ﺩ.ﺇ 701 | ﺩ.ﺇ 948 | ﺩ.ﺇ 1,304 | ﺩ.ﺇ 856 | ﺩ.ﺇ 698 | ﺩ.ﺇ 393 | ﺩ.ﺇ 349 |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
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