
Vacation rentals with a pool in Old Orchard Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Old Orchard Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

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.

*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.

Private Bungalow w/ Hot Tub, Free Parking & Pool
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Resort-like 2 bed/1 bath - seasonal pool/hot tub
Munjoy Hill is Portland's premiere neighborhood. Enjoy ocean views along the Promenade. Share our seasonal private pool/hot tub with us from May thru Oct (dates vary). We have a swing set, lounge chairs, grill, play cornhole, tennis (we supply racquets/balls) watch baseball, basketball or take a walk to the playground close by. A short walk to East End Beach and the waterfront trail lead you to the famous Old Port. This property is one of a kind in the city
Popular amenities for Old Orchard Beach rentals with a pool
House rentals with a pool

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

Pool and walking distance to beaches! Amenities!

35x18Pool| Hot Tub| Private Oasis w/ Deck | Yard

Unique Church Accommodation • Sebago Lake • Pool • Fire Pit

2BR, Sea & Relax w/ Wells Reserve View

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

Maritime Meadows - Charming Resort-Style Home!

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

Cozy Coastal Condo in Wells - Hot Tub & Pool!

NEW Classy Ogunquit Retreat! Pools, Walkable!

Little Nubble Nook - Beach Condo

Centrally located Ocean Towers condo in Ogunquit

Starfish Condo Wells Beach

Awesome get away spot in Wells!

Seaside Condo w/stunning views, 2 Queen sized beds

Drake's Island Beach Area Studio
Other vacation rentals with a pool

Maine Coastal Village Getaway

Willow Creek Homestead Indoor Pool Lake Access

Freshly Renovated, Family-Friendly Coastal Cottage

Cozy Beach Cottage - Wells, ME

Secluded Rustic Log Cabin on Beautiful Frye Island

Generic Two Bedroom - Stair access only

Lovely Beach house in GRB - Heated pool!

Sleeps 6, Pool, Hot Tub, Arcade, Gym, Near Beach
When is the best time to visit Old Orchard Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$45,736 GYD | G$47,615 GYD | G$49,286 GYD | G$52,210 GYD | G$48,451 GYD | G$55,342 GYD | G$73,094 GYD | G$73,094 GYD | G$41,768 GYD | G$43,438 GYD | G$46,989 GYD | G$48,659 GYD |
| 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 Old Orchard Beach

Total vacation rentals
Explore 160 vacation rentals in Old Orchard Beach

Nightly prices starting at
Old Orchard Beach vacation rentals start at G$10,442 GYD per night before taxes and fees

Verified guest reviews
Over 1,790 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
160 of Old Orchard Beach vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Old Orchard Beach rentals

4.7 Average rating
Old Orchard Beach stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Québec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Island of Montreal Vacation rentals
- Jersey City Vacation rentals
- Cottage rentals Old Orchard Beach
- Condo rentals Old Orchard Beach
- Rentals with a fire pit Old Orchard Beach
- House rentals Old Orchard Beach
- Waterfront rentals Old Orchard Beach
- Rentals with a hot tub Old Orchard Beach
- Rentals with a washer and dryer Old Orchard Beach
- Pet-friendly rentals Old Orchard Beach
- Rentals with a fireplace Old Orchard Beach
- Family-friendly rentals Old Orchard Beach
- Villa rentals Old Orchard Beach
- Cabin rentals Old Orchard Beach
- Beach house rentals Old Orchard Beach
- Serviced apartment rentals Old Orchard Beach
- Rentals with beach access Old Orchard Beach
- Beach condo rentals Old Orchard Beach
- Apartment rentals Old Orchard Beach
- Townhouse rentals Old Orchard Beach
- Rentals with a patio Old Orchard Beach
- Rentals with outdoor seating Old Orchard Beach
- Fitness-friendly rentals Old Orchard Beach
- Beachfront rentals Old Orchard Beach
- Rentals with pools York County
- Rentals with pools Maine
- Rentals with pools United States
- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Popham Beach State Park
- North Hampton Beach
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- East End Beach
- Gooch's Beach
- Gunstock Mountain Resort
- Coastal Maine Botanical Gardens
- Funtown Splashtown USA
- Crescent Beach State Park
- Footbridge Beach
- Wolfe's Neck Woods State Park




