Vacation 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.

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Guest favorite

Tiny home in Thornton

4.97 out of 5 average rating, 198 reviews

Small cabin in the White mountains

This small cabin has recently been re-built with new pine paneled walls and ceiling, bunk beds, carpeting, electricity, a new Eco-outhouse!, solar shower and It is located at the edge of a field about 100 yards from our home. It is a perfect base camp for hikers 12 miles south of Franconia notch trail heads and Appalachian Trail crossing. The cabin is most often used by hikers who want a base camp near many of the most popular hiking trails near Franconia Notch. It is a peaceful and quiet place.

Aug 1 – 8

R1,727 ZAR per night

Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 662 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

Aug 30 – Sep 6

R2,284 ZAR per night

Guest favorite

Guest suite in Derry

4.92 out of 5 average rating, 142 reviews

Derry home with year round amenites

Private basement apartment with ensuite bathroom, living area with television and kitchenette. Space for up to 4 guests, with a large king size bed and a queen sofa bed. The sofa bed is better for children than 2 full size adults. We do not take same day bookings. We do not allow pets. Our pool is available for our guests to use as well. It is not heated, so best during June, July and August months! This is a no smoking property As the space is a basement we do live in the house above.

Aug 27 – Sep 3

R2,034 ZAR per night

Guest favorite

Home in Kittery

4.92 out of 5 average rating, 100 reviews

Quiet Home with heated inground pool, waterfront

Private guest home in a quiet Kittery Point neighborhood on saltwater Barter's Creek with a heated inground pool with diving board and slide for guests . Close to local Kittery Point and York beaches, historic forts, landmarks, and Portsmouth, NH. A large deck with great views of the saltwater inlet. Two+ acres of land with a large landscaped yard with lawn games , private woods, and a long driveway. You have your own private waterfront on a salt water inlet with a canoe for your use. .

Jun 5 – 12

R6,419 ZAR per night

Guest favorite

Condo in Laconia

4.9 out of 5 average rating, 331 reviews

Million Dollar View! Weir's Beach 1/4 mile away!

This top floor-corner unit is a peaceful oasis. The elevator will whisk you up to your private studio apartment. Your view is breathtaking in any season....See the autumn leaves change in New England.....Ski nearby Gunstock in the winter, enjoy the short walk to Weirs Beach in the summer. Centrally located in the Lakes Region and all its attractions, shopping and restaurants! 1/4 mile to Weirs Beach, 4 miles to the Bank of NH Pavilion/Meadowbrook concert venue, 6 miles to Gunstock Mountain.

Nov 3 – 10

R1,771 ZAR per night

Guest favorite

Guesthouse in Belmont

4.99 out of 5 average rating, 200 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

Dec 23 – 30

R2,332 ZAR per night

Guest favorite

Cottage in York

4.98 out of 5 average rating, 118 reviews

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!

May 15 – 22

R3,851 ZAR per night

Guest favorite

Guesthouse in North Andover

4.97 out of 5 average rating, 186 reviews

Spacious Studio Guesthouse at Winery w/ Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Sep 16 – 23

R8,036 ZAR per night

Guest favorite

Home in Scarborough

4.98 out of 5 average rating, 229 reviews

Swim spa under the starry night pool/hot tub/sauna

Dreams do come true! Stay here and experience the pleasure of your own private Solar powered and Eco friendly spa resort getaway in Maine! Experience your own private spa in a four season sunroom with a heated indoor fitness pool of 90 degrees and a hot tub at 101 degrees. Boost your immune system with hydrotherapy. With an outdoor sauna steps away, and a fire pit this is truly a treat. We are close to beaches, lighthouses and Portland's Old Port just minutes away.

Apr 6 – 13

R7,563 ZAR per night

Guest favorite

Guest suite in Saco

4.99 out of 5 average rating, 105 reviews

Secret Garden Suite

This completely remodeled private suite is in a quiet neighborhood just footsteps from Marston's Marina. We are a bikeable 1.5 miles to the Saco beaches and an easy 5 minute drive to the bustle of Old Orchard Beach, or you can avoid it completely. This apartment with kitchenette and bath is designed for two, but can also accommodate new parents with a baby or toddler. Relax on the balcony overlooking the gardens and heated pool or take a dip to cool off!

May 13 – 20

R2,794 ZAR per night

Guest favorite

Guest suite in New Boston

4.99 out of 5 average rating, 170 reviews

Cozy, Private In-Law Suite with Hot Tub

#TheBarnQuiltHouse Cozy, private guest suite in the wooded hills of a quaint New Hampshire farming town. Residential neighborhood, centrally located in Southern New Hampshire. 20+/-min to Concord, Manchester Airport, St. Anselms College, New England College, Pat's Peak, Crotched Mountain. Head north to the lakes region, west to Mt. Sunapee, or south to visit Boston..all within an hour drive. May the peace of the wilderness be with you.

Sep 15 – 22

R4,866 ZAR per night

Guest favorite

Home in North Andover

4.94 out of 5 average rating, 127 reviews

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!

Jan 10 – 17

R16,257 ZAR per night