
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.

Attitash Retreat
Cozy spot for 4, plus your furry friend! (Must be 21 to check-in, no cats) Less than a mile from Attitash Mountain Resort, this spot is home base for your next adventure. IF YOUR DOG IS JOINING YOU, please provide advanced notice, a $25/night pet fee for the first 4 nights (max$100), that rabies vaccination records be provided at check in, and that your dog have access to a crate for times that you must leave him/her behind! One dog is permitted per room, no cats. Thank you for understanding.

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!
Your crew 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Apt in Victorian Mansion w/ Pool, Hot Tub, Parking
Mixing contemporary styling with old-world charm, the Apartment in the 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 seasonal pool, or relax by the fire pit, our half-acre yard offers a tranquil experience. The apartment has a chef's kitchen, dining, and living room with gas fp. NB., use of the living room bed may incur a charge. Please ask There is a L2 EV charging outlet. #allarewelcome

Spectacular Mountain Views, at Eagle Ridge !
Eagle 🦅 Ridge North Conway/ Intervale NH . You have the entire condo to share with family/ friends. Mountain Adventures with get togethers right here. Hiking Trails Frogs pond Swimming Tennis Kite flying & more. Trails End “Ice Cream” Rated best ski town in NH. Easy access to Mt. Washington and the Valley. Mt. Cranmore Wildcat Attitash Brenttwoods King Pines Story land Scenic Railroad Saco River canoeing/tubing Fishing StoryLand Saco River canoeing/tubing Tax free shopping

Peaceful suite in Boston with city views
Enjoy Boston in an elegant 2 bedroom/bath with sleek interior furnishing for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

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.

Spacious vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Stunning Mountain Views! Cozy Studio Resort Condo
Be inspired as you relax to the sound of the Pemigewasset River Flowing by. Enjoy your favorite beverage on our balcony as you gaze at the gorgeous Loon Mountain. Cozy Studio Apartment is nested at the base of Loon Mountain South Peak Ski trails! Central to all that Lincoln has to offer! Walking distance to fantastic restaurants and pubs. Minutes to Loon Ski Resort, The Flume Gorge, Lost River, Clarkes Trading Post, Franconia Notch, Ice Castles 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.

3 BR Cozy + Renovated Cabin in the White Mountains
Welcome to Birchwood Lodge, located in the cherished Waterville Estates neighborhood! Enjoy the comforts of home, coupled with the amenities of a resort! Relax in front of the warm pellet stove, curl up with a book on the loft, or create home-cooked meals in the brand new, open-concept kitchen. Enjoy unique details and design throughout the space, and then head out to explore the White Mountain region all year long.

Steps from Harbor, Pool, Backyard Garden, Parking
HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces
Popular amenities for Kittery rentals with a pool
House rentals with a pool

Nana-tucket Inn

Cozy & updated Loon MTN condo

Amazing House, Peaceful Shangri-La w/Pool &Hot-Tub

Designers Dream Home with Pool!

Large Loon Condo w/Amenities- Gas Fireplace

Spectacular log home with private pool and hot tub

The Hurkle Durkle House

On Attitash - Ski, Hike, Swim!
Apartment rentals with a pool

Large 3 bedroom/3 bath condo Lincoln, NH

Studio Condo in Hotel Resort at Loon Mountain

Ski Condo on Cranmore Mountain-Pool and Hot tub!

Loon Mountain River Oasis

Steps from Beach | Pool | Parking | Large Deck

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

Studio w/hot tub, pool, sauna, arcade & gym

Starfish Condo Wells Beach
Other holiday rentals with a pool

Maine Coastal Village Getaway

Freshly Renovated, Family-Friendly Coastal Cottage

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

Beach Dreaming

Headers’ Haven

Misty Harbor - Ski Gunstock!

Luxury Retreat In Back Cove | 10 Min to Downtown

Contemporary Cottage With Ocean View 32
When is the best time to visit Kittery?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £90 | £87 | £76 | £88 | £123 | £143 | £193 | £265 | £174 | £142 | £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 |
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
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Long Sands Beach
- Scarborough Beach
- Canobie Lake Park
- Crane Beach
- York Harbor Beach
- North Hampton Beach
- Willard Beach
- Short Sands Beach
- Cape Neddick Beach
- Gunstock Mountain Resort
- Gooch's Beach
- East End Beach
- Salem Willows Park
- Funtown Splashtown USA
- Bear Brook State Park
- Crescent Beach State Park
- Footbridge Beach
- Palace Playland
- Snhu Arena
- Singing Beach




