
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.

Cozy Studio apt w/pool & hot tub Ski Loon Mountain
This stylishly renovated Studio resort condo is the perfect getaway to enjoy White Mountains! Nestled at the base of Loon Mountain's South Peak, you will relish in the breathtaking mountain scenery and stunning hiking trails. After exploring, enjoy the onsite indoor pools and Jacuzzi. Great restaurants are just a few steps away, and the Pemigewasset River is accessible right out the backdoor! This studio condo comfortably sleeps 4 and provides you and your family with an unforgettable getaway!

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

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.

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 suitable for a child Updated / Modern Studio Condo directly on “ The Kanc” Main st Lincoln Walking to restaurants 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!
Popular amenities for Kittery rentals with a pool
House rentals with a pool

Townhouse near Gunstock, Bank of NH Pav, Ellacoya

Nana-tucket Inn

Faith Lane with community pool

Cozy & updated Loon MTN condo

Spacious vacation unit in premium suburban town

Sanctum by the Lake

2BR, Sea & Relax w/ Wells Reserve View

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Apartment rentals with a pool

Fantastic Location in the White Mountains

Attitash Studio | 5min to Storyland| Pools

Private 3 Br- 2 level - Townhouse in Forest Ridge

Studio Condo in Hotel Resort at Loon Mountain

Lovely studio with beautiful view of loon Mountain

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

Cozy mountain getaway

Cozy Condo at The Seasons- 2 Bedrooms
Other holiday rentals with a pool

Cozy, with Lots of Space

North Shore Getaway for Adults

Sterling 1BR at Everett | Pool & Gym

Pretty Boutique Studio, Pools, Walk to Everything!

Beachside Bliss: Hampton North Beach Condo

Starfish Condo Wells Beach

Cottage in Wells Maine

Lux home near Rt 3/MHT/mountain/lake/ocean/Boston
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 101 | € 97 | € 85 | € 99 | € 138 | € 160 | € 216 | € 297 | € 195 | € 127 | € 133 | € 115 |
| 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 € 58 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
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Canobie Lake Park
- Crane Beach
- North Hampton Beach
- East End Beach
- Salem Willows Park
- Willard Beach
- Short Sands Beach
- Gooch's Beach
- Funtown Splashtown USA
- Gunstock Mountain Resort
- Cape Neddick Beach
- Bear Brook State Park
- Crescent Beach State Park
- Palace Playland
- Footbridge Beach
- Singing Beach
- Ogunquit Playhouse




