Holiday rentals with a pool in Kittery

4.92 out of 5 average rating, 184 reviews

Home in Derry

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.

5 out of 5 average rating, 39 reviews

Apartment in Salisbury

North Shore Getaway for Adults

Adult Only Retreat! Escape to Salisbury! Our spacious 2 Beds, 1 bedroom apartment is perfect for mature adults seeking, relaxation, or adventure. Explore the North Shore's stunning beaches, lakes, scenic trails, restaurants and breweries. Relax and Reconnect: Unwind in our beautiful shared pool after a day of exploration. This owner-occupied property offers a peaceful escape with all the amenities. Prime Location: close to NH and Maine, perfect base for day trips. Book your retreat today!

5 out of 5 average rating, 8 reviews

Apartment in Wells

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

Welcome to 'Well Ashore', a charming 1-bedroom, 1-bathroom condo just 1 mile from the breathtaking Wells Beach- One of Maine's 7 -mile pristine sandy beaches. Ideal for couples or small families, this cozy retreat features a serene, nautical-inspired ambiance perfect for relaxation. Our condo is 4 miles from The Marginal Way, one of New England's most cherished coastal walks. This 1.25 mile scenic path offers stunning ocean views, plentiful benches, and an easy access to downtown Ogunquit.

4.83 out of 5 average rating, 24 reviews

Apartment in Wells

Dbl Bed/Pool/Hot Tub/Patio/Fitness/Playground

SeaMist 122 is conveniently located 1.5 Miles to Wells Beach, close to shopping and restaurants. Short walk to Scoop Deck Ice Cream, Bow Street Beverages, EAST Restaurant & Lounge, Bread & Roses Bakery and much more! With 2 Queen beds comfortably sleeps 4 . Wake up right with in room coffee bar including k-cups, creamers, variety of sugars, tea and hot cocoa. No need to worry about rain on your vacation, if it is not perfect beach weather, retreat to the stunning indoor pool and hot tub.

4.95 out of 5 average rating, 40 reviews

Home in Kittery

Fantastic Kittery Home with Pool

Modern New Englander boasting a large, private backyard with pool (seasonal, from May to Oct, approx). Our comfortable, 3-bedroom home is a commuter's dream. Working from home? Use our separate dedicated office space with 1 gig WiFi. Playing hooky? So many options! Walk or bike to the fabulous eateries, shopping or breweries our area has to offer! Enjoy our pool or take a short drive to the beach! (Please note, our pool is normally unheated. For an additional $40 a day we'll heat it!)

4.97 out of 5 average rating, 228 reviews

Guesthouse in Belmont

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.

4.94 out of 5 average rating, 148 reviews

Cottage in Wells

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.

4.97 out of 5 average rating, 137 reviews

Cottage in York

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!

4.76 out of 5 average rating, 134 reviews

Condo in Wells

Generic Two Bedroom - Stair access only

Our two-bedroom units are located on the first, second or third floor in our all-stair property. All of our two-bedroom units have two bedrooms, with a varying number of beds, two bathrooms, full kitchen, living room, dining room and patio/balcony. They have a washer and dryer too! All kitchens come equipped with standard dishes, baking and cooking supplies, as well as full size appliances! Best for larger families to spread out! Room requests are accepted but not guaranteed.

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 118 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

4.93 out of 5 average rating, 104 reviews

Guest suite in Standish

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.

4.93 out of 5 average rating, 118 reviews

Cottage in Plum Island

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.

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Popular amenities for Kittery rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 44 reviews

Home in Hampton

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

DeniseRating, 5 stars6 days ago

We enjoyed our stay so much! The house was perfect for our vacation. Plenty of room that everyone had their own space. The house is beautifully decorated, made you feel right at home. Comfortable seating found throughout inside and outside area. Teresa has thought of EVERYTHING, and it is available for you to use on your stay. The location is fantastic, a short walk to North Beach in a nice quiet residential neighborhood. We would highly recommend and would stay here again!

4.85 out of 5 average rating, 109 reviews

Home in Barnstead

Locke Lake Waterfront Escape

AlexRating, 5 stars5 days ago

Great and relaxing location, close to local amenities. Perfect for small groups, Hillary was awesome to rent from.

4.81 out of 5 average rating, 283 reviews

Home in Campton

Addie Shack in the White Mountains

AlisaRating, 5 stars9 months ago

Michael was fantastic with responding quickly, this home was beautiful & is a great location if you're looking to visit the white mountains! my friends & I had a great stay, we would definitely book again!

4.95 out of 5 average rating, 127 reviews

Home in North Deering

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

IrmaRating, 5 stars2 weeks ago

Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

4.93 out of 5 average rating, 326 reviews

Home in Campton

Spectacular log home with private pool and hot tub

MadonnaRating, 5 stars2 weeks ago

we had a great time at this house. very clean and comfortable! Definitely worth it! we would stay here again.

4.82 out of 5 average rating, 135 reviews

Home in Derry

Beautiful Lakefront Vacation

BobRating, 5 stars9 months ago

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

4.83 out of 5 average rating, 42 reviews

Home in Kennebunk Beach

Kennebunk's Charming Beach Home

BrennaRating, 5 stars2 weeks ago

We had a wonderful stay. The house was spotless and beautiful with a fully stocked kitchen, super comfortable beds, and great amenities. Our kids loved the heated pool , hot tub, board games, and the easy walk to the beach. The location is also great and close to lots of restaurants and shopping. Stephanie was very kind, helpful, and quick to respond to any questions.

4.89 out of 5 average rating, 123 reviews

Home in Barnstead

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

AndresRating, 5 stars1 month ago

The house is beautiful and the views are just breathtaking. From inside the house, you get a beautiful view of the lake and then the porch is amazing. You can kayak, use the paddle board or use the canoe. You can also sit by the lake and enjoy the campfire. The surroundings are very beautiful and peaceful. The host is very responsive, solved all our doubts and was flexible with us during check-in and check-out, which we appreciated very much. At check-in, we were greeted by a great bottle of wine and chocolates, which was a great touch. The house also has a ping pong table, books to read and board games. The kitchen was well stocked with the basics. We had an amazing stay, we highly recommend this property :)

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Condo rentals with a pool

5 out of 5 average rating, 18 reviews

Condo in Hampton

Lovely 2 BR beach condo with inground pool

PhyllisRating, 5 stars9 months ago

We had a wonderful vacation in NH especially due to the beautiful condo we stayed in. Every morning we took a short walk to the beach at sunrise. We also enjoyed sitting out on the deck overlooking the pool as well. It was a short drive to most places of interest, shops and restaurants. Our host Sue was very responsive via text. The place was clean and full of many things to help make our stay special. We’ll definitely be back in the future.

4.9 out of 5 average rating, 278 reviews

Condo in Campton

The Alpine Oasis

KaraRating, 5 stars4 days ago

The condo was very comfortable and clean! Easy in and had everything we needed for our weekend stay. Adorably decorated. We appreciated the A/C in the bedrooms at night for a comfortable sleep. Finding A/C is not easy in that area! Thank you for a great stay!

4.73 out of 5 average rating, 108 reviews

Condo in Laconia

Breathtaking Lake View! Hot tub! Concerts! Lake!

KatrinaRating, 5 stars8 months ago

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.

4.97 out of 5 average rating, 38 reviews

Condo in Hampton Beach

Ocean View - Steps to the Beach!

AngeloRating, 5 stars9 months ago

We stay at Hampton Beach every year for a few days. This has by far been the best. It seemed we were at home. Copmmunication with the owner and the facility was exceptional.

4.94 out of 5 average rating, 158 reviews

Condo in Laconia

1 Bedroom/1 Bath Condo @ Lake Winnipesaukee

SandraRating, 5 stars1 week ago

Great stay, easy check in and check out. Very clean and comfortable accommodations! Would stay again for sure

4.91 out of 5 average rating, 363 reviews

Condo in Laconia

Million $ View of Lake Winni Flexible check in/out

NathanRating, 5 stars1 month ago

The place was great. Quiet with beautiful views. Lots of games which was helpful because it rained a lot during our stay. 10/10 would recommend and stay again. Host was very helpful and kind. The woman that cleaned the pool was also very sweet. My 8 year old was itching to swim in the freezing pool when it wasn’t quite ready and she offered to come to our room and let us know when she was done. Thank you for having us!

4.95 out of 5 average rating, 101 reviews

Condo in Wells

Relaxing Beachside Condo with Pool at Wells Beach

MaryRating, 5 stars1 month ago

Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.