
Holiday 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.

Condo in Old Orchard Beach
Your Perfect Old Orchard Beach Getaway This beautiful condo (Unit 19), is the ideal retreat to experience the best of Old Orchard Beach! This family friendly property offers the perfect balance of comfort and convenience. Just a short walk to the pier, downtown, and the beach! Includes: - 2 bedrooms, each w/fan and balcony - Pool - Washer & Drier - 2 Smart TVs - Microwave - 4 burner cooktop - Kitchen Table - Sofa - Refrigerator - Toaster - Keurig - Parking for 1 vehicle (paid parking close by)

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!

Our Beach House Getaway
A great find describes this newly built spacious three bedroom cape style home located in peaceful private neighborhood setting with pool and parking conveniently located close to Maine Turnpike. Our home is only 1.2 miles from downtown Old Orchard Pier, Beach, shops and attractions! Step outside and catch a ride downtown on The Old Orchard Beach Seasonal Trolley or visit nearby restaurants and ice cream shop within walking distance! Our home offers many extras for a fun filled relaxing stay!

"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.

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

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.

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.

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

Treehouse Farm - Sebago

Ogunquit River Outlook

Pool and walking distance to beaches! Amenities!

The Lodge at Hidden Pines

Unique Church Stay • Sebago Lake • Pool • Fire Pit

2BR, Sea & Relax w/ Wells Reserve View

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

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

30 second walk to Beach- Pool-Outdoor Shower

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Classy Ogunquit Studio! Pools, Kitchen, Walkable!

Centrally located Ocean Towers condo in Ogunquit

Our Happy Place!

Awesome get away spot in Wells!

Relaxing Beachside Condo with Pool at Wells Beach

Steps to Beach, Pier, Park | Condo with Pool • 6
Other holiday rentals with a pool

Make this family-friendly cottage your summer spot

Sea Salt Stay

Freshly Renovated, Family-Friendly Coastal Cottage

Cottage 2 @ Coast Village Inn

Contemporary Cottage With Ocean View 13

Cabin in the woods with pool and lake access

Sleeps 6, Pool, Hot Tub, Arcade, Gym, Near Beach

2 BR house, close to Ogunquit, w/ AC + golf cart!
When is the best time to visit Scarborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £172 | £171 | £171 | £175 | £174 | £187 | £256 | £255 | £150 | £152 | £124 | £150 |
| 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 holiday rentals with a pool in Scarborough

Total holiday rentals
Explore 200 holiday rentals in Scarborough

Nightly prices starting at
Scarborough holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 3,370 verified reviews to help you choose

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
190 of Scarborough holiday rentals include wifi access

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

4.7 Average rating
Scarborough stays receive an average rating of 4.7 out of 5 from guests
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- Sebago Lake
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