Vacation rentals with a pool in Boothbay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Boothbay

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

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Top guest favorite
The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.
Loft in Falmouth
4.95 out of 5 average rating, 687 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.

Top guest favorite
A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.
Home in North Deering
4.96 out of 5 average rating, 163 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 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

Guest favorite
Home in Old Orchard Beach
4.95 out of 5 average rating, 141 reviews

OOB Oasis: 6BR Home w/ Private Pool Near Beach

Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built home offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, new hot tub and sparkling in-ground pool; perfect for summer fun, fall gatherings, or relaxing after a day at the beach.

Guest favorite
A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.
Home in Deering Center
4.83 out of 5 average rating, 117 reviews

There's No Place Like Home

Our home is filled with cozy spaces to relax and unwind. From the outside deck and pool to the quaint private bedrooms! This family friendly BnB provides a kitchen, dining room and two living areas for a vacation haven . This home has the feel of a true BnB, yet the entire space is dedicated to our guests. We are on site in our in-law quarters, so are close at hand for questions and help if needed. Our home is located in a convenient, quiet and safe neighborhood with off street parking.

Top guest favorite
The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.
Guest suite in East End
4.93 out of 5 average rating, 132 reviews

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Munjoy Hill is Portland's premiere neighborhood. Enjoy ocean views along the Promenade. Share our seasonal private pool/hot tub with us from May thru Oct (dates vary). We have a swing set, lounge chairs, grill, play cornhole, tennis (we supply racquets/balls) watch baseball, basketball or take a walk to the playground close by. A short walk to East End Beach and the waterfront trail lead you to the famous Old Port. This property is one of a kind in the city

Top guest favorite
A refreshing pool area is surrounded by well-kept landscaping and seating options. Two blue umbrellas provide shade over metal chairs and tables. Colorful pool floats are positioned in the clear water, and a charming white structure is visible in the background.
Apartment in Falmouth
4.97 out of 5 average rating, 113 reviews

Poolside Suite-Gateway to Portland

Beat summer heat with a private inground secluded pool. 7 minutes from downtown Portland. Bus line to Old Port across street. Parking in my driveway Walk to Mackworth Island from suite.. Sandy small beaches for accessing water/sunbathing . Casco Bay surrounds neighborhood for walking/biking. Pastry, fresh brewed coffee provided. Kurig in suite. The suite accommodates 2 adults. No children please. Backyard and pool available to the 2 suite guests only

Top guest favorite
A spacious living area features a plush leather sofa and an easy chair, arranged around a circular coffee table atop a textured area rug. A wall-mounted smart TV is visible, while a dining space with multiple chairs is seen in the background.
Apartment in North Deering
4.95 out of 5 average rating, 108 reviews

Portland Sweet Escape

Get to know Portland like a local from this beautiful, centrally-located apartment. This home is just steps from Portland’s Sebago to Sea walking trail and is a 10-15 minute drive from great local breweries, East End Beach, and Historic Old Port. Featuring beautiful hardwood floors throughout, the three-bedroom + office interior comes fully furnished with updated amenities and a fresh, contemporary design. Linens, towels and beach towels are included.

Top guest favorite
The image showcases a pool area overlooking the water, framed by lush greenery and colorful wildflowers. Lounge chairs are positioned around the pool, with a shed visible nearby. The calm water reflects a clear blue sky, creating a serene setting.
Home in Boothbay Harbor
4.95 out of 5 average rating, 21 reviews

Port Cabin by Sea Maine

On the water, at the tip of Linekin Bay, sits this four-bedroom, two-bath cottage with a private swimming pool. The cottage has a modern, fully equipped kitchen (regular drip coffee maker) with a dining area that is perfect for gathering. The upstairs has two bedrooms with a queen-sized bed in each, while the downstairs has two double bunk bedrooms. There are two full bathrooms, one on each floor, and a spacious laundry room on the first floor.

Guest favorite
Home in South Thomaston
4.94 out of 5 average rating, 106 reviews

Large private area, close to Rockland

Quiet and private neighborhood. Perfect for family or group getaways. Kid friendly. One mile from public ocean access, (WesKeag River) Five miles from downtown Rockland, and just minutes from downtown Thomaston. Three beautiful beaches within five miles. It’s the perfect place to stay while exploring the coastline, enjoying the downtown shops and restaurants, hiking and exploring the nearby cultural attractions. Two night minimum.

Guest favorite
A serene community pool is surrounded by a spacious deck with lounge chairs for relaxation. Tall trees in the background provide a natural setting, while neighboring homes are visible, enhancing the sense of community.
Home in Old Orchard Beach
4.96 out of 5 average rating, 106 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 at Elmwood and Marcotte Motors Motel can take you right to the beach.

Guest favorite
A log cabin is nestled among tall trees on a gentle slope. Large windows create airy views from the exterior, showcasing a front deck that extends along the house. The natural surroundings provide a peaceful and serene setting.
Home in Peru
4.94 out of 5 average rating, 233 reviews

the lake house

My place is close to the beach and family-friendly activities. My place is good for couples, solo adventurers, families (with kids), and furry friends (pets). Mt Washington , north Conway New Hampshire , Sunday river ski area , oxford casino , storyland , Santa village ,

Top guest favorite
A warm orange wall serves as a backdrop for a vibrant deer painting. A purple sofa is positioned in front, accompanied by a patterned pillow and a modern lounge chair. A tall plant adds texture, while a decorative oriental carpet covers the floor.
Apartment in Cumberland Mills
4.96 out of 5 average rating, 187 reviews

A Riot of Color at an Artist's Retreat on the Portland Line

The apartment is on the first floor. There are two entrances with five steps each. It's a nice space with original art on the walls and oriental carpets throughout. The back door leads to a private deck that is all yours and the deck leads to the pool!

Popular amenities for Boothbay rentals with a pool

When is the best time to visit Boothbay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,112 ZARR1,933 ZARR1,771 ZARR8,123 ZARR8,123 ZARR6,238 ZARR8,025 ZARR8,123 ZARR8,123 ZARR6,612 ZARR2,843 ZARR2,827 ZAR
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

Quick stats about vacation rentals with a pool in Boothbay

  • Total vacation rentals

    Explore 80 vacation rentals in Boothbay

  • Nightly prices starting at

    Boothbay vacation rentals start at R1,787 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 160 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Boothbay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Boothbay rentals

  • 4.6 Average rating

    Boothbay stays receive an average rating of 4.6 out of 5 from guests

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