
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.

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.

"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

Privacy, River, Pond, A frame Hot Tub EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. 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. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Portland & Beach & Lighthouses! Romantic! Lovely
Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

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.

OOB Oasis: 5BR 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, and sparkling in-ground pool—perfect for summer fun, fall gatherings, or simply relaxing after a day at the beach.

Luxury Retreat In Back Cove | 10 Min to Downtown
Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Tower Suite w/ Hot Tub, W/D, & Parking
This newly renovated, gorgeous, spacious suite, located on the 3rd floor of our 1865 mansion, is just 10 mins to downtown and the airport. Relax by the firepit or soak in our hot tub and enjoy our gardens. We are owner-operated. The suite includes a newly renovated bath with rain shower and radiant floor heating; W/D; lounge and kitchenette w/ work table; and a large bedroom. Our half-acre yard provides ample space for privacy. Level 2 EV station is available #allarewelcome

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

Sunny West End Guest Suite w/Harbor Views and Pool
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

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

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.
Popular amenities for Boothbay rentals with a pool
House rentals with a pool

Luxe Liberty: Getaway with Heated Indoor Pool!

Stay Together in Style

*Close to Beach*POOL* *5 Star Reviews*

House in the woods

Spacious 5BR Cottage w/Pool, Water & Resort Access

Designers Dream Home with Pool!

Ocean View Retreat with Heated Pool / Hot Tub

There's No Place Like Home
Condo rentals with a pool

30 second walk to Beach- Pool-Outdoor Shower

Stylish Designer Retreat on Langsford with Pool

Stars And Stripes

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Condo in Old Orchard Beach

RARE 3 bedroom at The Resort Goose Rocks Beach!

Samoset-Affordable Luxury

Lovely 2 bedroom riverside condo with pool
Other vacation rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Home Near Beaches & Fun

Treehouse Farm - Sebago

Coastal Retreat with Pool and Cheerful Vibes

Our Beach House Getaway

Heart of Rockland Maine

Beautiful 2 B/R home, 5 minute walk to the beach

The Hurkle Durkle House

Saco Cozy Cottage! Minutes From Old Orchard Beach!
When is the best time to visit Boothbay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $684 CAD | $684 CAD | $684 CAD | $684 CAD | $684 CAD | $525 CAD | $676 CAD | $684 CAD | $684 CAD | $557 CAD | $239 CAD | $238 CAD |
| Avg. temp | -6 °C | -5 °C | 0 °C | 6 °C | 12 °C | 17 °C | 21 °C | 20 °C | 16 °C | 9 °C | 3 °C | -2 °C |
Quick stats about vacation rentals with a pool in Boothbay

Total vacation rentals
Explore 110 vacation rentals in Boothbay

Nightly prices starting at
Boothbay vacation rentals start at $164 CAD per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
110 of Boothbay vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Boothbay rentals
Destinations to explore
- Plainview Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Québec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Island of Montreal Vacation rentals
- Quebec City Area Vacation rentals
- Mont-Tremblant Vacation rentals
- Laval Vacation rentals
- House rentals Boothbay
- Rentals with a washer and dryer Boothbay
- Boutique hotels Boothbay
- Pet-friendly rentals Boothbay
- Rentals with a kayak Boothbay
- Family-friendly rentals Boothbay
- Rentals with an EV charger Boothbay
- Waterfront rentals Boothbay
- Rentals with outdoor seating Boothbay
- Hotel rooms Boothbay
- Apartment rentals Boothbay
- Rentals with a firepit Boothbay
- Rentals with a home theater Boothbay
- Beachfront rentals Boothbay
- Cabin rentals Boothbay
- Rentals with a patio Boothbay
- Fitness-friendly rentals Boothbay
- Rentals with breakfast Boothbay
- Rentals with a hot tub Boothbay
- Rentals with a fireplace Boothbay
- Rentals with an accessible height bed Boothbay
- Cottage rentals Boothbay
- Rentals with lake access Boothbay
- Rentals with beach access Boothbay
- Rentals with pools Maine
- Rentals with pools United States
- Sebago Lake
- Scarborough Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- East End Beach
- Pemaquid Point Lighthouse
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- The Camden Snow Bowl
- Wolfe's Neck Woods State Park
- Palace Playland
- Maine Maritime Museum
- Farnsworth Art Museum
- Hills Beach
- Bradbury Mountain State Park
- Portland Museum of Art
- Fortunes Rocks Beach
- Rockland Breakwater Light
- Aquaboggan Water Park
- Bug Light Park
- Pineland Farms




