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

Total vacation rentals
Explore 70 vacation rentals in Portland

Nightly prices starting at
Portland vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 5,350 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 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, Crescent Beach State Park, and Portland Museum of Art
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.
4.95 out of 5 average rating, 700 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
Beach House w/ Heated Pool · Fire Pit · Kennebunk
Perfect home for hosting and entertaining! Private in-ground pool, 600+ sq. ft. sprawling deck, large yard, and close proximity to beaches, restaurants, and shopping. Brand new renovations throughout! Amenities and features include: Newly renovated top to bottom 2 beautiful kitchens w/ granite, stainless steel appliances In-ground pool and 600 sq. ft. wrap-around deck Spacious 2 acre yard One mile from the beach Walking distance to Kennebunk Lower Village/Kennebunkport Dock Square Pet friendly!
4.83 out of 5 average rating, 179 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
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
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.
4.84 out of 5 average rating, 126 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 reviews
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 a small child. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.
4.98 out of 5 average rating, 289 reviewsPopular amenities for Portland rentals with a pool
House rentals with a pool

Faith Lane with community pool
4.96 out of 5 average rating, 123 reviews
Moose Pond Mountain Escape
4.89 out of 5 average rating, 180 reviews
Lovely Beach house in GRB - Heated pool!
4.98 out of 5 average rating, 58 reviews
Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast
4.99 out of 5 average rating, 76 reviews
The Hurkle Durkle House
5.0 out of 5 average rating, 34 reviews
Unique Church Stay • Sebago Lake • Pool • Fire Pit
4.96 out of 5 average rating, 71 reviews
Oceanfront Cottage 3 in OOB
4.89 out of 5 average rating, 9 reviews
Wanderer House | Private 3BR Home + Pool & Bikes
5.0 out of 5 average rating, 3 reviewsCondo rentals with a pool

Steps to Wells Beach + Pool | Coastal Retreat
4.96 out of 5 average rating, 130 reviews
Luxury Coastal Retreat | Mins from Dock Square
4.99 out of 5 average rating, 67 reviews
Condo in Old Orchard Beach
4.97 out of 5 average rating, 33 reviews
LUXURY OCEANFRONT CONDO Best Location on the beach
5.0 out of 5 average rating, 26 reviews
*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM
4.85 out of 5 average rating, 67 reviews
OOB Beach Suite|2 Queen Beds | Pool|Sleeps 4 (#10)
5.0 out of 5 average rating, 12 reviews
Cozy Coastal Condo in Wells - Hot Tub & Pool!
4.98 out of 5 average rating, 63 reviews
The Ocean's Belle
4.91 out of 5 average rating, 33 reviewsOther vacation rentals with a pool

Maine Coastal Village Getaway
4.98 out of 5 average rating, 50 reviews
Pool+Hot Tub+Sauna Near Beaches Spa Retreat
4.96 out of 5 average rating, 74 reviews
*Close to Beach*POOL* *5 Star Reviews*
4.83 out of 5 average rating, 47 reviews
Crosswinds Cottage 17
4.71 out of 5 average rating, 7 reviews
Cottage on 50 Acres | Lakeside + Tennis + Hot Tub
4.98 out of 5 average rating, 55 reviews
Four Story Townhouse With Ocean View 55
4.97 out of 5 average rating, 33 reviews
Secluded Rustic Log Cabin on Beautiful Frye Island
4.96 out of 5 average rating, 49 reviews
Kennebunk's Charming Beach Home
4.68 out of 5 average rating, 63 reviewsWhen is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 595 | ﺩ.ﺇ 595 | ﺩ.ﺇ 514 | ﺩ.ﺇ 687 | ﺩ.ﺇ 668 | ﺩ.ﺇ 1,076 | ﺩ.ﺇ 1,370 | ﺩ.ﺇ 1,553 | ﺩ.ﺇ 1,105 | ﺩ.ﺇ 881 | ﺩ.ﺇ 735 | ﺩ.ﺇ 643 |
| 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 |
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