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

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

Kennebunk/Kennebunkport Beach House w/Pool!
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!

"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

Designers Dream Home with Pool!
Discover this brand-new, beautifully appointed 2-bedroom home nestled within a secure, private community surrounded by 200 acres of preserved natural beauty. Enjoy full access to outdoor heated pools, a clubhouse featuring a game room (with ping pong, foosball, shuffleboard, and a poker room), and a fully equipped fitness center to keep you on routine. Mingle with fellow guests at the clubhouse or relax in your peaceful, private backyard, and enjoy the perfect balance of activity and serenity.

Historic Schoolhouse c1866 Winter & Summer Dates
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.

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 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 stay. The apartment has a chef's kitchen, radiant heat floors in the kitchen and bathroom. Use of the living room daybed linens may incur a charge. Please ask. There is a L2 EV charging outlet. #allarewelcome

*Close to Beach*POOL* *5 Star Reviews*
New, beautiful 3BR/2.5BA home is ideal for your next family summer vacation! Located 1 mile from one of Maine's most popular beaches, this light & airy house is set up perfectly for a couple with main floor master bedroom & en suite bathroom, or plenty of room for the entire family with 2 comfortable bedrooms and bathroom upstairs. Amenities include community pool, wi-fi, Smart TV, and washer/dryer. Other nearby fun attractions include beach, golf courses, local shopping & fresh seafood.

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.

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

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

The Lodge at Hidden Pines

The Nest | Lake Access, Pool, HotTub, 5BDRM, Sauna

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

Maritime Meadows - Charming Resort-Style Home!

There's No Place Like Home

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Lovely Beach house in GRB - Heated pool!
Condo rentals with a pool

30 second walk to Beach- Pool-Outdoor Shower

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

Little Nubble Nook - Beach Condo

Pretty Boutique Studio, Pools, Walk to Everything!

Starfish Condo Wells Beach

Relaxing Beachside Condo with Pool at Wells Beach

Cozy, clean, 2nd floor condo in Conway, NH!

Peaceful Pines Saco River Getaway
Other vacation rentals with a pool

Maine Coastal Village Getaway

Cottage by the sea

Sea Salt Stay

Freshly Renovated, Family-Friendly Coastal Cottage

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

Cozy Beach Cottage - Wells, ME

Beautiful 2 bedrm cottage in Beach Dreams complex

Cabin in the woods with pool and lake access
When is the best time to visit Scarborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ841 | ﺩ.ﺇ837 | ﺩ.ﺇ837 | ﺩ.ﺇ859 | ﺩ.ﺇ852 | ﺩ.ﺇ918 | ﺩ.ﺇ1,256 | ﺩ.ﺇ1,249 | ﺩ.ﺇ735 | ﺩ.ﺇ746 | ﺩ.ﺇ610 | ﺩ.ﺇ735 |
| 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 Scarborough

Total vacation rentals
Explore 210 vacation rentals in Scarborough

Nightly prices starting at
Scarborough vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 3,390 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
200 of Scarborough vacation rentals include wi-fi access

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

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