
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.

Cozy Private Studio Unit w/ Laundry and Parking!
Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

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.

Cozy Condo at Attitash!
Enjoy activities & beautiful scenery offered at Attitash Mountain Village, in the White Mountains! This cozy one bedroom, 2nd floor condo sleeps four, and includes a completely renovated kitchen/living area and bathroom! You will be just steps away from a beautiful pool pavilion, tennis courts, playgrounds, the Saco River Beach, hot tubs, fire pits, an arcade, and a fitness center. Nestled among all the summer attractions of the area- 10 minutes to Story Land! Always something fun to do!

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.

Stylish and Cozy at Revere Beach
Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Luxury Suite Jacuzzi Pool White Mtns. River Front
Amazing location in heart the White Mountains Clubhouse, Beach, Lake, Pool, Hot Tub, River, Tennis, Racquetball, Gym, Sauna, Wally-ball, Game rooms, Grills, nature trails on site, Ice skating, and more. Shuttle to Loon River View Best Amenities In the Area Perfect for Romantic Retreat/Skiing/ Hiking. Jacuzzi tub, spa shower and zen design in unit! Close to-Scenic Kancamagus, hikes, Loon, waterpark, and Ice Castles. Walk to Cafe Lafayette Dinner Train & Woodstock Inn Brewery.

Romantic Bungalow w/ Hot Tub & Parking
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

White Mountain Resort Pool/HotTub Shuttle to Loon
Perfect for a single or couple Luxurious but affordable Private but located inside a resort with top notch amenities Quiet & Clean Queen bed with sofa bed suitable for a child Updated / Modern Studio Condo directly on “ The Kanc” Main Street Lincoln Walking to restaurants, pubs and shops, easy access to The White Mountains - Lincoln NH Hiking skiing, zip-lining, ice castles, shopping, Clarks Trading Post, Cannon and Loon Mountain, Santa’s Village, and more

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.

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!

The Haven at Doherty Homestead
Our pricing is transparent; there are no cleaning fees or surprise costs. Looking for a cozy place to crash after adventuring about? One hour from Boston, the ocean or the mountains, we are 10 minutes from city life as well as local hiking spots. Prefer a restful respite? Our backyard is your oasis; firepit, meditation treehouse, hammocks and patio area complete with a dining table, outdoor TV and lounge furniture.

Family friendly + Mountain Views @amountainplace
Our Family-Friendly, Mountain View Townhouse is tucked away but just an 8 minute drive to downtown North Conway. Relax by the gas fireplace, soak in the views, cook in the updated kitchen, swim in the heated outdoor pool (open Memorial Day to Labor Day) or head out the backyard to find hiking trails. Great proximity to all the White Mountains has to offer. Don’t miss out!
Popular amenities for Kittery rentals with a pool
House rentals with a pool

Nana-tucket Inn

Faith Lane with community pool

Cozy & updated Loon MTN condo

Spacious vacation unit in premium suburban town

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Designers Dream Home with Pool!

Privacy, River, Pond, A frame Hot Tub EPIC Views,

Stylish Mtn Home-Ski/ Pools/ Hot Tubs & Fire Pit
Apartment rentals with a pool

Attitash Studio | 5min to Storyland| Pools

The Alpine Oasis

Lovely studio with beautiful view of loon Mountain

Cozy mountain getaway

White Mountain Farmhouse

AttitashResort! 1-flr, studio, secure check-in

Cozy Studio with Loon Mountain Views

Studio w/hot tub, pool, sauna, arcade & gym
Other holiday rentals with a pool

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Stylish Designer Retreat on Langsford with Pool

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

Hampton Beach Bailey's Resort

Steep Falls Escape, river & falls just steps away

Cottage in Wells Maine

Luxe Eco Studio near Back Cove

2 BR house, close to Ogunquit, w/ AC + golf cart!
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £89 | £85 | £75 | £86 | £121 | £140 | £189 | £260 | £171 | £139 | £78 | £70 |
| 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 £51 per night before taxes and fees

Verified guest reviews
Over 1,410 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!
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- Rentals with pools York County
- Rentals with pools Maine
- Rentals with pools United States
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Scarborough Beach
- Long Sands Beach
- Canobie Lake Park
- York Harbor Beach
- Crane Beach
- North Hampton Beach
- Willard Beach
- East End Beach
- Short Sands Beach
- Salem Willows Park
- Gooch's Beach
- Cape Neddick Beach
- Gunstock Mountain Resort
- Funtown Splashtown USA
- Bear Brook State Park
- Crescent Beach State Park
- Palace Playland
- Footbridge Beach
- Singing Beach
- Peabody Essex Museum




