
Vacation rentals with a pool in Portland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Portland
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.

Apt in Victorian Mansion w/ Hot Tub & Parking
Mixing contemporary styling with old-world charm, the Apartment in the Registered Chapman House offers a relaxing private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by the fire pit, our half-acre yard offers a tranquil experience. The apartment has a chef's kitchen, dining, and living room with gas fp. NB., use of the living room bed may incur a charge. Please ask There is a L2 EV charging outlet. #allarewelcome

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.

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.

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.

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.

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

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

Treehouse Farm - Sebago

Beach Dreams Cottage w/ Central A/C

Our Beach House Getaway

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

2BR, Sea & Relax w/ Wells Reserve View

Old Falls Retreat-4BR w Gorgeous River View & Pool

Spacious 5BR Cottage w/Pool, Water & Resort Access
Condo rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Stylish Designer Retreat on Langsford with Pool

Two-Bedroom Condo on the Wells/Ogunquit town-line

Condo in Old Orchard Beach

Our Happy Place!

Starfish Condo Wells Beach

Steps to Beach, Pier, Park | Condo with Pool • 6

Barefoot in Maine
Other vacation rentals with a pool

Cottage by the sea

Secluded Rustic Log Cabin on Beautiful Frye Island

Paradise Found Minutes from Ogunquit | Heated Pool

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

Saco Cozy Cottage! Minutes From Old Orchard Beach!

Cottage in Wells Maine

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

The Sunroom Suite-Abbott Brook Inn unit 1
When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,187 GYD | G$47,460 GYD | G$44,533 GYD | G$45,996 GYD | G$67,740 GYD | G$60,422 GYD | G$77,984 GYD | G$88,438 GYD | G$62,931 GYD | G$50,178 GYD | G$41,815 GYD | G$36,588 GYD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about vacation rentals with a pool in Portland

Total vacation rentals
Explore 60 vacation rentals in Portland

Nightly prices starting at
Portland vacation rentals start at G$10,454 GYD per night before taxes and fees

Verified guest reviews
Over 5,020 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Portland vacation rentals include wi-fi access

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

4.8 Average rating
Portland stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Portland's top spots, include Peaks Island, Portland Museum of Art, and Crescent Beach State Park
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River 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
- Jersey City Vacation rentals
- East Side Vacation rentals
- Rentals with a fire pit Portland
- Villa rentals Portland
- Rentals with a kayak Portland
- Mansion rentals Portland
- Rentals with a patio Portland
- Townhouse rentals Portland
- Beach house rentals Portland
- Rentals with a hot tub Portland
- Rentals with an EV charger Portland
- Fitness-friendly rentals Portland
- Rentals with a sauna Portland
- Private suite rentals Portland
- Rentals with a washer and dryer Portland
- Cottage rentals Portland
- Cabin rentals Portland
- Beachfront rentals Portland
- Boutique hotels Portland
- Family-friendly rentals Portland
- Hotel rooms Portland
- House rentals Portland
- Apartment rentals Portland
- Rentals with breakfast Portland
- Rentals with beach access Portland
- Condo rentals Portland
- Rentals with a fireplace Portland
- Waterfront rentals Portland
- Pet-friendly rentals Portland
- Rentals with outdoor seating Portland
- Rentals with pools Cumberland County
- Rentals with pools Maine
- Rentals with pools United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- King Pine Ski Area
- Cranmore Mountain Resort
- Willard Beach
- East End Beach
- Short Sands Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- Cape Neddick Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Palace Playland
- Conway Scenic Railroad
- Footbridge Beach
- Things to do Portland
- Art and culture Portland
- Food and drink Portland
- Sports activities Portland
- Tours Portland
- Things to do Cumberland County
- Food and drink Cumberland County
- Sightseeing Cumberland County
- Sports activities Cumberland County
- Art and culture Cumberland County
- Tours Cumberland County
- Things to do Maine
- Sports activities Maine
- Tours Maine
- Nature and outdoors Maine
- Food and drink Maine
- Sightseeing Maine
- Things to do United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States
- Tours United States






