
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)

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

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.

Lux 2BR Apt w/ Pool and Gym
Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

Hotel Style room w/pool, stunning Mountain view
Stylishly renovated Hotel room at the Lodge at Lincoln Station resort. Sleeps 2. Featuring King bed, Microwave and coffee maker. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

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.

Sunny West End Guest Suite w/Harbor Views and Pool
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

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!

Breathtaking View, <3mins to Loon, NEW Renovation!
Welcome to our cozy, modern and NEW renovated 2-bedroom property located in the beautiful town of Lincoln, New Hampshire. With comfortable sleeping arrangements for up to 4 guests and 1 bathroom, our property offers a convenient and comfortable base for exploring the stunning White Mountains region. Step outside and discover a world of adventure, from hiking to skiing, water sports to sightseeing.
Popular amenities for Kittery rentals with a pool
House rentals with a pool

Townhouse near Gunstock, Bank of NH Pav, Ellacoya

Nana-tucket Inn

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

Faith Lane with community pool

Cozy & updated Loon MTN condo

Sanctum by the Lake

Deer Park-Shuttle-Amenities- Fireplace

2BR, Sea & Relax w/ Wells Reserve View
Apartment rentals with a pool

Private 3 Br- 2 level - Townhouse in Forest Ridge

Steps from Beach | Pool | Parking | Large Deck

Cozy mountain getaway

White Mountain Farmhouse

1 Bedroom/1 Bath Condo @ Lake Winnipesaukee

Elevate Your Adventure: Book Slope side Now!

Million $ View of Lake Winni Flexible check in/out

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

Maine Coastal Village Getaway

Freshly Renovated, Family-Friendly Coastal Cottage

Serenity by the Sea

Everything's "Well Ashore"- 1 mile to Wells Beach!

Pretty Boutique Studio, Pools, Walk to Everything!

Centrally located Ocean Towers condo in Ogunquit

The Ocean's Belle

Cottage in Wells Maine
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £90 | £86 | £76 | £88 | £122 | £142 | £191 | £263 | £173 | £141 | £79 | £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 £52 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
- Long Sands Beach
- Scarborough Beach
- Canobie Lake Park
- York Harbor Beach
- Crane Beach
- North Hampton Beach
- Short Sands Beach
- Willard Beach
- East End Beach
- Cape Neddick Beach
- Gooch's Beach
- Salem Willows Park
- Gunstock Mountain Resort
- Funtown Splashtown USA
- Bear Brook State Park
- Crescent Beach State Park
- Footbridge Beach
- Palace Playland
- Singing Beach
- Peabody Essex Museum




