Holiday rentals with a pool in Boothbay Harbor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Boothbay Harbor

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Loft in Falmouth

4.95 out of 5 average rating, 609 reviews

Loft Apartment on Tree-Lined Street in Falmouth

Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Superhost

Home in Kennebunk

4.84 out of 5 average rating, 37 reviews

Kennebunk's Charming Beach Home

Well located, our charming cozy home is just an easy stroll, less than 1 mile away from Mother's beach. 5 minutes drive from all the shop and restaurants of Kennebunkport. There are 5 comfortable bedrooms, 4 upstairs and 1 on the main floor and 2 bathrooms. The private backyard is perfect to enjoy and feel the sea breeze. Enjoy the hot tub and the heated pool, volley ball court, fire pit, plenty of space for parking. A great place to create memories with your friends and family! Contact us!

Guest favourite

Home in Kennebunk

4.83 out of 5 average rating, 143 reviews

Kennebunk/Kennebunkport Beach House w/Pool!

Perfect home for hosting and entertaining! Private in-ground pool, 600+ sq. ft. sprawling deck, large yard, and close proximity to beaches, restaurants, and shopping. Brand new renovations throughout! Amenities and features include: Newly renovated top to bottom 2 beautiful kitchens w/ granite, stainless steel appliances In-ground pool and 600 sq. ft. wrap-around deck Spacious 2 acre yard One mile from the beach Walking distance to Kennebunk Lower Village/Kennebunkport Dock Square Pet friendly!

Guest favourite

Home in Portland

4.95 out of 5 average rating, 122 reviews

"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 eateries and breweries. 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

Top guest favourite

Flat in Portland

4.98 out of 5 average rating, 402 reviews

Apt in Victorian Mansion with Hot Tub & Parking

Mixing contemporary styling with an old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub or relax at a fire pit, our half-acre yard provides privacy for all guests. The fully private Apartment has an indoor gas fireplace, an elegant kitchen, dining, and living room. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

Top guest favourite

Flat in Portland

4.98 out of 5 average rating, 250 reviews

Maine Hacienda w/hot tub & seasonal pool

Our renovated suite at the foot of Deering Highlands is a 10 minute drive to downtown Portland. A cozy, quiet, modern space with a maritime edge. A short walk to Woodford’s corner and Forest Ave - home to many restaurants & coffee shops. The space includes a seasonal pool and year-round hot tub. Ideal for singles, couples or couples with one or two small children. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.

Superhost

Tiny home in Harrison

4.89 out of 5 average rating, 303 reviews

Million $ views, Hot Tub, Crooked River- Private

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

Guest favourite

Home in Arundel

5 out of 5 average rating, 5 reviews

Cheerful 2 Bdrm Home with Pool!

Immaculate 2 bdrm condo in private gated community. Unlimited access to 2 outdoor heated pools, clubhouse with game room (ping pong, foosball, shuffleboard, poker room) and fitness center. Enjoy social gatherings with other guests at the clubhouse or dine-in at your wooded backyard setting. Nestled within a 200-acre nature preserve in a modern community that has miles of walking/biking trails. A short drive away from Portland and Kennebunkport, ME and minutes to close by beaches.

Guest favourite

Guest suite in Standish

4.93 out of 5 average rating, 104 reviews

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.

Top guest favourite

Guest suite in Saco

4.99 out of 5 average rating, 126 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!

Guest favourite

Cabin in West Paris

4.94 out of 5 average rating, 107 reviews

Cabin on the hill!

Check out our reviews! Take it easy at this unique and tranquil getaway with views. Private hot tub and sauna. Have your own amenities but close enough to everything. Skiing, hiking, fishing, hunting and so much more. 20 min to Norway lake, mt. Abrams and bryant pond. 30 to bethel and 40 to Sunday river. Atv and snow mobile trails are close. Plenty of room for trailers for toys! Wood fired sauna with changing room in garage! Great views year round.

Guest favourite

Home in Old Orchard Beach

4.98 out of 5 average rating, 80 reviews

Faith Lane with community pool

Newly built open concept with gorgeous quartz counters and vanities. 4 spacious bedrooms so large parties will be very comfortable. Deck with gas grill, table and chairs, and kids picnic table. Community pool and only minutes drive to the beach and pier. Located in the brand new Church Street Station community. The beach trolley stop is right at the entrance to the complex so makes for an easy quick ride to the beach.