
Holiday rentals with a pool in Scarborough
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Scarborough

Total holiday rentals
Explore 210 holiday rentals in Scarborough

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

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

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

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
200 of Scarborough holiday rentals include wifi 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!
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.

"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

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

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

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 + 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.

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.

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.

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!

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.

Saco Cozy Cottage! Minutes From Old Orchard Beach!
2026 Season is here ! Great rates…Come enjoy some quiet time in this quaint cozy cottage! Keep it simple at this peaceful and centrally- located place. 2-bedroom condo each with new queen beds…Sleeper sofa available. Enjoy the hustle and bustle during the season May-Oct. Everything is close by from shopping markets up the street to restaurants at Old Orchard. Seven-minute drive to Old Orchard Beach. Head to Portland headlights which is a 20 min drive!!!

Quiet 2BR Suite · Saltwater Pool · Walk to OOB
Escape the noise without giving up the fun. Sea Salt Stay is a bright, self-contained retreat in a quiet Old Orchard Beach neighborhood — close enough to walk or hop the trolley to the beach and pier, far enough to actually sleep at night. Whether you're here for a full family beach week, a quiet weekend away, or a comfortable base while you explore the Maine coast, this is your place.
Popular amenities for Scarborough rentals with a pool
House rentals with a pool

Faith Lane with community pool

1 mile to OOB pier | Outdoor fire pit | Game room

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast

Our Beach House Getaway

Unique church accommodation • Sebago Lake • Pool • Fire pit

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

Maritime Meadows – Charming Resort-Style Home!

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!

Steps to Beach, Pier, Park | Condo with Pool • 11

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

Pretty Boutique Studio, Pools, Walk to Everything!

Condo in Old Orchard Beach

Our Happy Place!

Steps to Wells Beach + Pool | Coastal Retreat
Other holiday rentals with a pool

Maine Coastal Village Getaway

Cottage by the sea

Studio Condo, Deck, Pool, Hot Tub, Playground

Walk to Wells Beach! July dates available!

Paradise Found Minutes from Ogunquit | Heated Pool

Brand new 2 b/r tiny home, 5 minute walk to beach

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

Cozy rustic cottage near the beach
When is the best time to visit Scarborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £147 | £176 | £189 | £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 |
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Willard Beach
- Short Sands Beach
- Scarborough Beach
- North Hampton Beach
- Pemaquid Beach
- Footbridge Beach
- Pemaquid Point Lighthouse
- East End Beach
- Cape Neddick Beach
- Popham Beach State Park
- Coastal Maine Botanical Gardens
- Gooch's Beach
- King Pine Ski Area
- Hills Beach
- Jenness Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Things to do Scarborough
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