
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
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Popular amenities for Kittery rentals with a pool
House rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home
Heather’s place was by far the most well maintained and clean Airbnb our family has ever stayed in. She was responsive and kind with all our needs. The pool was conveniently located right across the road and a beautiful place to spend the warmer day. Walking to the OOB trolly, seafood restaurants and the best ice cream place we’ve visited yet. We look forward to making Heather’s place and a trip to the Maine coast an annual family vacation.

Nana-tucket Inn
We had an absolutely wonderful experience staying at this Airbnb! The home was impeccably clean, cozy, and well-stocked with everything we could possibly need. The host's attention to detail was evident in every corner, from the kids' toys to the thoughtful touches like snacks, coffee, and local guidebooks. The location was perfect—peaceful and quiet but still close to shops and restaurants. I especially loved relaxing in front of the fire and enjoying the serene surroundings. The host was incredibly responsive and went above and beyond to ensure our stay was seamless, offering great tips about the area and checking in (without being intrusive). I highly recommend this spot to anyone visiting North Andover or the greater Boston area.

Locke Lake Waterfront Escape
Me and my family had an awesome stay. The house was great with lots of space and places to sleep. We were 8 ppl and there was more than enough room. Garage/game room was awesome I just wish it was insulated with some heat we had to wear our coats to be comfortable, of course the weather was 26F so it was expected. The rest of the house was warm and cozy. I would love to rent this same house in the summer it must be amazing with the view of the lake. One more thing is although there are 2 bathrooms its more like 1 because the second bathroom upstairs has a little door that leads to the room with the 4 beds so the other people not staying in that room didn’t use that bathroom to not get walked in on unexpectedly. Overall I still gave this place 5 stars and it’s one of the best places I’ve stayed and the host is very responsive and accommodating.

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK
Thank you for allowing us to stay at your beautiful home. The photos did it no justice! I can’t wait to be back, we will be stay here again.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!

Beautiful Lakefront Vacation
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Kennebunk's Charming Beach Home
Hi Patrick, We had a wonderful time at your home. it was delightful and cosy. Everything was as described and I loved how everything was set up. It was very easy to communicate with you. It was wonderful that the beach was 3 mins down the road and there was plenty to do nearby. Thank you sp much again for a very special stay. I would love to come back again. Jill B
Apartment rentals with a pool

2-bdrm/2-bath condo near Weirs Beach w/pool
It was a nice place to stay for the weekend. We were looking for something close to Weirs Beach and it was just up the hill. We had a little trouble getting in when we first arrived as the instructions were a little confusing, but a quick text on Airbnb resulted in a quick response that got us inside. Otherwise was a good place to stay.

Breathtaking Lake View! Hot tub! Concerts! Lake!
The room had beautiful views of the lake as mentioned in the listing. The space was clean and nicely decorated and provided everything we needed for our short stay. The property also had other amenities for us to use such as a pool, hot tub, game room and community balcony. The location was also very good as is close to the beautiful lake and picturesque towns. Would recommend their place overall as was an enjoyable weekend stay.

1 Bedroom/1 Bath Condo @ Lake Winnipesaukee
Mikes place was a great stay while in. New Hampshire. Lots of stuff to do on the lake and everything you need is within walking distance!! I nightly recommend this condo on the lake

It’s "Lake Time" you just found your happy place!
Cozy stay minutes away from Weirs Beach! Convenient location and lots to do. Jason was a great host with great communication and hospitality. Thank you for sharing your space!

Village Hideaway
Excellent place and hosts, highly recommended. Don met us in the place and showed us around and made us feel at home. The apartment was beautiful, extremely well stocked, and very comfortable. The location is great as it's very quiet but also very close to local amenities and the highway.

Walk to Weirs from this Spacious Condo!
This is our second time staying at Lisa’s place. It is in a perfect location right in the heart of the lake region. The pool is amazing. Lisa keeps the place perfectly clean and has everything you could need. We can’t wait to stay again.

Lakeview Condo in Laconia
Nice roomy comfortable space for two moms and three adult children. The condo was clean and beautifully decorated. Good location for getting to Bank of NH for a concert. Within driving distance to restaurants, grocery stores and Weirs beach. We didn't know how to adjust a digital thermometer. I had to message Ryan late at night. He got back to me right away and was super helpful. We had a memorable and pleasant time enjoying the lakes region of NH. Thank you, Ryan!

NEW Beachside Wells Beach Condo with Pool
The Wells Beach condo was very comfortable and clean. It was off season so it was pleasantly quiet. It is very close to a great beach with a long stretch to walk and great for swimming and sunbathing in the good weather. There was a pool right outside the condo door which would be super convenient in the warm weather. The condo is well maintained and the ability to walk across the street to the beach is a great benefit. Plus there are restaurants and shops close by,
Quick stats about holiday rentals with a pool in Kittery
Total rentals
20 properties
Nightly prices starting at
£60 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Hampton Beach
- Wells Beach
- North Hampton Beach
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Long Sands Beach
- Good Harbor Beach
- Crane Beach
- Rye North Beach
- East End Beach
- Aaronap Cellars
- Pavilion Beach
- Water Park of New England
- Wentworth by the Sea Country Club
- Manchester Country Club - NH
- Bear Brook State Park
- Canobie Lake Park
- Phillips Beach
- Gas House Basin
- Halibut Point State Park
- West Beach
- Breakfast Hill Golf Club
- Crescent Beach