
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)

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

"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

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

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast
Relax with a private pool, spacious deck, and easy access to Maine’s beautiful seacoast. Perfect for families and groups to enjoy outdoor living. ✱ Sleeps 10–12, cozy with 12 ✱Private 35x18 pool with floaties and lounge chairs ✱Deck with grill, mini fridge, and seating ✱Spacious 2100 sq ft open layout ✱Fully stocked kitchen, coffee and tea ✱Fast WiFi and smart TVs ✱Foosball, games, and record player ✱Comfortable beds with quality linens ✱Crib and high chair available ✱Ample off street parking

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

NoCo Village King/Jacuzzi
Welcome to Village Place at the Eastern Slope Inn! Must be 21 to check-in, $40 authorization taken at check-in (not an actual charge), no cats. IF YOUR PUP IS JOINING YOU, please provide advanced notice, a $25/night pet fee for the first 4 nights, RABIES RECORDS, and a crate if you must leave them behind. One dog is permitted per room, no cats, thanks for understanding. Located halfway between The Eastern Slope Inn and Cranmore Mountain, this second floor unit is walking distance to it all!

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, clean, 2nd floor condo in Conway, NH!
The condo is a quiet family space in a great location: we are located 10 minutes to the Settlers Green outlets/ shopping, close to skiing, hiking , Saco River, Conway Lake and much more. Easy access to all the amenities Conway has to offer. Two portable AC units were installed in living room and dining room only . You will receive the code for the lock box on the front door in the morning of your arrival. ***Quiet time is heavily enforced 10:00pm - 8:00am***
Popular amenities for Scarborough rentals with a pool
House rentals with a pool

Family Fun with Community Pool

The Lodge at Hidden Pines

Our Beach House Getaway

Unique Church Accommodation • Sebago Lake • Pool • Fire Pit

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

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

Downtown North Conway with private pool & hot tub!

Maritime Meadows – Charming Resort-Style Home!
Apartment rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

Peaceful Ogunquit Studio, Pool, Kitchen, Walkable!

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

Elevate Your Adventure: Book Slope side Now!

Wells Beach Coastal Condo w/ Pool – Steps to Ocean

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

Cozy Family Retreat with Saco River Access
Other holiday rentals with a pool

Cottage by the sea

Quiet 2BR Suite · Saltwater Pool · Walk to OOB

Live OOB! 1 mile from Ocean, New, Clean & Comfy

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

Saco Cozy Cottage! Minutes From Old Orchard Beach!

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

Luxury Retreat In Back Cove | 10 Min to Downtown

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 | €169 | €203 | €218 | €202 | €200 | €216 | €295 | €293 | €173 | €175 | €143 | €173 |
| 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 210 holiday rentals in Scarborough

Nightly prices starting at
Scarborough holiday rentals start at €43 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with a firepit Scarborough
- Family-friendly rentals Scarborough
- Flat rentals Scarborough
- Rentals with a washing machine and dryer Scarborough
- Rentals with beach access Scarborough
- Rentals with a kayak Scarborough
- Boutique hotels Scarborough
- Townhouse rentals Scarborough
- House rentals Scarborough
- Serviced apartment rentals Scarborough
- Cabin rentals Scarborough
- Rentals with a fireplace Scarborough
- Fitness-friendly rentals Scarborough
- Rentals with outdoor seating Scarborough
- Rentals with an EV charger Scarborough
- Guest house rentals Scarborough
- Pet-friendly rentals Scarborough
- Hotel rooms Scarborough
- Beach house rentals Scarborough
- Smoking-friendly rentals Scarborough
- Rentals with a hot tub Scarborough
- Private suite rentals Scarborough
- Rentals with breakfast Scarborough
- Apartment rentals Scarborough
- Rentals with a patio Scarborough
- Beachfront rentals Scarborough
- Cottage rentals Scarborough
- Rentals with a sauna Scarborough
- Waterfront rentals Scarborough
- Rentals with pools Cumberland County
- Rentals with pools Maine
- Rentals with pools United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Scarborough Beach
- Willard Beach
- North Hampton Beach
- Short Sands Beach
- Pemaquid Beach
- Popham Beach State Park
- East End Beach
- Pemaquid Point Lighthouse
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Footbridge Beach
- Wolfe's Neck Woods State Park
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Pleasant Mountain Ski Area
- Hills Beach
- Funtown Splashtown USA
- Things to do Scarborough
- Things to do Cumberland County
- Sightseeing Cumberland County
- Nature and outdoors Cumberland County
- Entertainment Cumberland County
- Tours Cumberland County
- Sports activities Cumberland County
- Food and drink Cumberland County
- Art and culture Cumberland County
- Things to do Maine
- Sports activities Maine
- Tours Maine
- Nature and outdoors Maine
- Sightseeing Maine
- Food and drink Maine
- Art and culture Maine
- Things to do United States
- Sports activities United States
- Entertainment United States
- Wellness United States
- Food and drink United States
- Sightseeing United States
- Nature and outdoors United States
- Art and culture United States
- Tours United States







