
Holiday rentals with a pool in Kittery
Find and book unique homes with a pool on Airbnb
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 £128 per night before taxes and fees

Verified guest reviews
Over 1,520 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!
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

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

Newly Renovated Studio Downtown!
The newly-renovated, newly furnished condo is located right in the center of everything that beautiful Ogunquit has to offer. Just a five minute walk to the beach and even closer to Ogunquit's landmark restaurants and bars, this is the most desirable location to stay in Ogunquit. Enjoy free on-site parking, a BBQ and on-site pool access. I am an artist, whose first professional gig was at the Ogunquit Playhouse just up the street, and appreciate your rental as a way to support local artists.

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.

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!)

OOB Oasis: 6BR Home w/ Private Pool Near Beach
Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built home offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, new hot tub and sparkling in-ground pool; perfect for summer fun, fall gatherings, or relaxing after a day at the beach.

Steps to Wells Beach + Pool | Coastal Retreat
Stay steps from Wells Beach in this renovated coastal condo with an onsite pool, clean modern interior, and prime walkable location off Atlantic Avenue. Walk to the sand in minutes, enjoy the ocean air from your patio, relax by the pool, and explore nearby shops, dining, playground, and arcade. Perfect for couples, small families, or a small group, this one bedroom condo makes an easy Southern Maine escape for visiting Wells, Ogunquit, Kennebunkport and the classic New England coast!

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.

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!
Popular amenities for Kittery rentals with a pool
House rentals with a pool

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Faith Lane with community pool

Theatre | Arcade | Pool w. Free 3 Car Parking

Spacious vacation unit in premium suburban town

Designers Dream Home with Pool!

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

The Stunning Melita Farms Geodesic Dome Farmhouse

Spacious Cape Neddick Coastal Home !
Apartment rentals with a pool

The Alpine Oasis

Serenity by the Sea

Small ’N Moody | Near Moody Beach & Ogunquit

Two-Bedroom Condo on the Wells/Ogunquit town-line

Little Nubble Nook - Beach Condo

Million $ View of Lake Winni Flexible check in/out

Neighborhood Nest | 10 minutes to Beach & Downtown

Lake Views | Pool | Walk to Weirs & Pavilion
Other holiday rentals with a pool

Maine Coastal Village Getaway

Surfview Two Bedroom w/ Pool Access

Beach Plum-Elegant Coastal Escape

Winnipesaukee All Season Getaway

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

Studio Condo, Deck, Pool, Hot Tub, Playground

BRAND NEW 2026: East Coastin' 2 bed/1 bath Cottage

Paradise Found Minutes from Ogunquit | Heated Pool
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £66 | £72 | £81 | £89 | £124 | £143 | £194 | £267 | £175 | £143 | £80 | £71 |
| 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 |
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Rentals with a hot tub Kittery
- Boutique hotels Kittery
- Rentals with breakfast Kittery
- Rentals with a firepit Kittery
- Beachfront rentals Kittery
- Rentals with a patio Kittery
- Fitness-friendly rentals Kittery
- Family-friendly rentals Kittery
- Rentals with a fireplace Kittery
- Waterfront rentals Kittery
- Cabin rentals Kittery
- Rentals with a washing machine and dryer Kittery
- Flat rentals Kittery
- Apartment rentals Kittery
- House rentals Kittery
- Rentals with outdoor seating Kittery
- Rentals with beach access Kittery
- Pet-friendly rentals Kittery
- Cottage rentals Kittery
- Rentals with pools York County
- Rentals with pools Maine
- Rentals with pools United States
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Long Sands Beach
- Canobie Lake Park
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- North Hampton Beach
- Crane Beach
- Scarborough Beach
- Footbridge Beach
- Cape Neddick Beach
- East End Beach
- Gooch's Beach
- Snhu Arena
- Good Harbor Beach
- Jenness Beach
- Salem Willows Park
- Salisbury Beach
- Gunstock Mountain Resort
- Hills Beach
- Salem Witch Museum
- Things to do Kittery
- Things to do York County
- Tours York County
- Nature and outdoors York County
- Sports activities York County
- Art and culture York County
- Food and drink York County
- Sightseeing York County
- Things to do Maine
- Sightseeing Maine
- Food and drink Maine
- Sports activities Maine
- Art and culture Maine
- Tours Maine
- Nature and outdoors Maine
- Things to do United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States







