
Vacation rentals with a pool in Freeport
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Freeport

Total vacation rentals
Explore 40 vacation rentals in Freeport

Nightly prices starting at
Freeport vacation rentals start at R 4,204 ZAR per night before taxes and fees

Verified guest reviews
Over 1,950 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Freeport vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Freeport rentals

4.8 Average rating
Freeport stays are highly rated by guests—averaging 4.8 out of 5!
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.
4.95 out of 5 average rating, 700 reviews
Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
Welcome to your Ogunquit Oasis, a luxurious 5-bedroom beach house located on the edge of Ogunquit Village. Walk to the beach, restaurants, Perkins Cove, Marginal Way & everything in Ogunquit! The house features a heated pool that reaches 104 degrees, ideal for all seasons. Built in 2014, the house includes central air, three Ultra HD TVs, and wireless speakers. The dining table seats 10, with an outdoor living room, grill, & gas firepit. Each spacious bedroom offers plush bedding & ceiling fans.
5.0 out of 5 average rating, 103 reviews
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
4.87 out of 5 average rating, 611 reviews
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
You 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, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022
4.97 out of 5 average rating, 174 reviews
Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only 10 min to downtown. Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by one of our fire pits, our half-acre yard offers a tranquil stay. The apartment boasts a newly renovated bathroom, radiant heated floors in both kitchen & bath, and a chef's kitchen. This grand apartment won't disappoint. L2 EV charging outlet on site #allarewelcome
4.97 out of 5 average rating, 518 reviews
Starfish Condo Wells Beach
Enjoy the amazing sunrise as well as marsh and ocean views from this spacious just renovated one and a half bedroom condo with queen bed and queen Murphy bed. Fully equipped kitchen with granite counter tops and stainless steel appliances. Updated full bath with tub. Located within walking distance to many local area restaurants. After a fun filled day on the beach relax by the salt water pool or in the hot tub. Shared gas grill, picnic area, playground and basketball hoop. Parking for one car
4.9 out of 5 average rating, 117 reviews
Pool, Dream Home Gym, TV+Desk Each Room, Games
Spectacular home gym, swimming pool, furnished deck! 4BR/2BA, living room w/ 85" TV. Sit/stand desk, chair, TV, prem cotton sheets, ceiling fans - ALL bedrooms. Two person basketball game & kid's air hockey. Two driveway basketball hoops! Kitchen: air fryer, blender, Keurig, coffee maker, dish washer, fully stocked utensils & dinnerware Gym: Plate loaded bench press, pulldown, squat. Rogue bike, squat rack, adj bench, DBs 5-55 lb, TV, kettlebells. Bean bag chairs, toddler toys. Fire pit.
5.0 out of 5 average rating, 10 reviews
Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.
5.0 out of 5 average rating, 140 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.
4.95 out of 5 average rating, 155 reviews
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.
4.95 out of 5 average rating, 179 reviews
LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!
4.97 out of 5 average rating, 197 reviews
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!
5.0 out of 5 average rating, 113 reviewsPopular amenities for Freeport rentals with a pool
House rentals with a pool

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL
4.87 out of 5 average rating, 113 reviews
Beach House w/ Heated Pool · Fire Pit · Kennebunk
4.83 out of 5 average rating, 179 reviews
There's No Place Like Home
4.84 out of 5 average rating, 126 reviews
Faith Lane with community pool
4.96 out of 5 average rating, 123 reviews
the lake house
4.94 out of 5 average rating, 236 reviews
Lovely Beach house in GRB - Heated pool!
4.98 out of 5 average rating, 58 reviews
The Hurkle Durkle House
5.0 out of 5 average rating, 34 reviews
Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast
4.99 out of 5 average rating, 76 reviewsCondo rentals with a pool

Newly designed one-bedroom condo- heart of OGT
4.97 out of 5 average rating, 105 reviews
Cozy Family Retreat with Saco River Access
4.91 out of 5 average rating, 149 reviews
3BR, 2BA condo in No. Conway, Close to everything!
4.98 out of 5 average rating, 198 reviews
Cozy, clean, 2nd floor condo in Conway, NH!
4.96 out of 5 average rating, 132 reviews
Elevate Your Adventure: Book Slope side Now!
4.83 out of 5 average rating, 118 reviews
Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6
4.93 out of 5 average rating, 126 reviews
The Gibson Building 3BR
4.97 out of 5 average rating, 123 reviews
Two-Bedroom Condo on the Wells/Ogunquit town-line
4.85 out of 5 average rating, 227 reviewsOther vacation rentals with a pool

POOL+Hot tub+6Private Acres+15 min to Sunday River
4.95 out of 5 average rating, 94 reviews
Secluded Rustic Log Cabin on Beautiful Frye Island
4.96 out of 5 average rating, 49 reviews
Oceanfront Cottage 1
4.9 out of 5 average rating, 20 reviews
Pool • Hot Tub +4K Movie Theater +Games +2 acres
4.89 out of 5 average rating, 71 reviews
Fall into Luxury, Free Heated Pool until oct 1st
5.0 out of 5 average rating, 44 reviews
Sugar Shack! Hot tub, pool, walk to town!
4.96 out of 5 average rating, 27 reviews
Maine Fall Getaway •Grill •Fire Pit •King Bed •EV
5.0 out of 5 average rating, 21 reviews
The Nest | Lake Access, Pool, HotTub, 5BDRM, Sauna
5.0 out of 5 average rating, 7 reviewsDestinations to explore
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Popham Beach, Phippsburg
- Willard Beach
- Scarborough Beach
- Footbridge Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Gooch's Beach
- Hills Beach
- Fortunes Rocks Beach
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Funtown Splashtown USA
- Palace Playland
- Portland Museum of Art
- Maine Maritime Museum
- Bradbury Mountain State Park
- Reid State Park





