
Holiday rentals with a pool in Freeport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Freeport
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

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

Maine Hacienda w/hot tube & 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.

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.

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.

Romantic Bungalow w/ Hot Tub & Parking
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

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.

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

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

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

Mountain Hideaway - Outdoor pool, hot tub

Luxe Liberty: Getaway with Heated Indoor Pool!

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

Stay Together in Style

Farmhouse: Ice Rink | Movie Cave | Hot Tub

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

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

Ski in/ski out Sunday River Condo Brookside 2a210

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

6 miles from Sunday River with heated outdoor pool

Our Happy Place!

Relaxing Beachside Condo with Pool at Wells Beach

Slope Side | Ground floor | Hot Tub, Pool, Sauna

Sunday River Resort Condos @Cascades

Sunday River Studio (Ski In/Out)
Other holiday rentals with a pool

Vacation Home Near Sunday River

Cozy Ski Cabin #2, 3 beds

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

Secluded Rustic Log Cabin on Beautiful Frye Island

Heated SwimSpa, Sauna, Games + 7mi to Sunday River

Ogunquit Downtown- 5 Mins from Playhouse and Beach

2 BR house, close to Ogunquit, w/ AC + golf cart!

Comfortable Maine Getaway with Thoughtful Touches
Quick stats about holiday rentals with a pool in Freeport

Total holiday rentals
Explore 10 holiday rentals in Freeport

Nightly prices starting at
Freeport holiday rentals start at $199 NZD per night before taxes and fees

Verified guest reviews
Over 90 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Freeport holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Freeport rentals

4.8 Average rating
Freeport stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Jersey City Holiday rentals
- East Side Holiday rentals
- Rentals with a fireplace Freeport
- Rentals with outdoor seating Freeport
- Rentals with beach access Freeport
- Bed and breakfasts Freeport
- Cabin rentals Freeport
- Cottage rentals Freeport
- House rentals Freeport
- Rentals with a fire pit Freeport
- Rentals with a washing machine and dryer Freeport
- Apartment rentals Freeport
- Pet-friendly rentals Freeport
- Waterfront rentals Freeport
- Rentals with a patio Freeport
- Rentals with breakfast Freeport
- Family-friendly rentals Freeport
- Rentals with pools Cumberland County
- Rentals with pools Maine
- Rentals with pools United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- King Pine Ski Area
- Willard Beach
- East End Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Palace Playland
- Footbridge Beach
- Pleasant Mountain Ski Area
- Maine Maritime Museum
- Ogunquit Playhouse
- Bradbury Mountain State Park
- Mt. Abram
- Hills Beach




