
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.

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.

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
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

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.

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.

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!

Mountain Paradise,Views,Hot Tub,Waterville Estates
Gorgeous New Home, Contemporary Rustic Style, everything you could wish for including HOT TUB on the covered part of the deck! Upscale everything with breathtaking views of Campton Valley, Golf Course and all Mountains in the Region from 60+ deck and every room in the house! Westerly exposure gives you opportunity to enjoy unforgettable sunset every night! Immaculately decorated with too many beautiful features to count. Brand new Weber grill and gas Fire pit on the deck.

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.

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.

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.

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.

Nana-tucket Inn
Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!
Popular amenities for Kittery rentals with a pool
House rentals with a pool

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Cozy Hideaway at Waterville Estates!

Rockport Pool House|4BR/3BA Walk to Bearskin Neck

Sleeps 10-4/2 Cozy Beach Cottage, Pool, Porch, BBQ

Spectacular log home with private pool and hot tub

There's No Place Like Home

Solar Plant Pool House

Kennebunk's Charming Beach Home
Condo rentals with a pool

The Alpine Oasis

Stylish Designer Retreat on Langsford with Pool

Studio condo, 2 queen beds, Laundry, restaurants

Ocean View - Steps to the Beach!

Hampton Beach Bailey's Resort

Condo in Old Orchard Beach

Starfish Condo Wells Beach

Relaxing Beachside Condo with Pool at Wells Beach
Other holiday rentals with a pool

Four Story Townhouse With Ocean View 55

North Shore Getaway for Adults

Bauhaus Retreat in Nature Preserve

Friends & Family Getaway • Pools • Views • Fire

Beachside Bliss: Hampton North Beach Condo

2BR, Sea & Relax w/ Wells Reserve View

Maritime Meadows - Charming Resort-Style Home!

Heron's Hide-Away
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 NZD | $200 NZD | $176 NZD | $203 NZD | $284 NZD | $329 NZD | $444 NZD | $611 NZD | $401 NZD | $262 NZD | $274 NZD | $238 NZD |
| 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 |
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 $17 NZD per night before taxes and fees

Verified guest reviews
Over 1,340 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Cottage rentals Kittery
- Cabin rentals Kittery
- Rentals with a washing machine and dryer Kittery
- Condo rentals Kittery
- Apartment rentals Kittery
- House rentals Kittery
- Rentals with outdoor seating Kittery
- Rentals with beach access Kittery
- Pet-friendly rentals Kittery
- Fitness-friendly rentals Kittery
- Waterfront rentals Kittery
- Family-friendly rentals Kittery
- Rentals with a fireplace Kittery
- Rentals with a fire pit Kittery
- Beachfront rentals Kittery
- Rentals with a patio Kittery
- Rentals with a hot tub Kittery
- Boutique hotels Kittery
- Rentals with breakfast Kittery
- Rentals with pools York County
- Rentals with pools Maine
- Rentals with pools United States
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Scarborough Beach
- Lynn Beach
- York Harbor Beach
- Long Sands Beach
- Good Harbor Beach
- Canobie Lake Park
- Crane Beach
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- East End Beach
- Salem Willows Park
- Dunegrass Golf Club
- Salisbury Beach State Reservation
- Willard Beach
- Funtown Splashtown USA
- Wentworth by the Sea Country Club
- Cliff House Beach
- Short Sands Beach
- Parsons Beach




