
Vacation rentals with a pool in Old Orchard Beach
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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

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

Luxury Oceanview Retreat | Mins from Dock Square
Minutes to Dock Square, beaches, and local restaurants. Escape to Cape Porpoise, Kennebunkport. Sea Glass is a luxury 1BR condo with ocean views, fire pit, designer interiors, a seasonal pool & LOCATION. Relax by the fire pit, walk to shops, explore the beaches, and enjoy a coastal retreat year-round. Perfect for getaways, remote work, or a classic Maine coast vacation. Experience Maine’s winter charm, spring beauty, beautiful summer and fall foliage at SeaGlass. Permit Number: STR-0008560

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.

*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.

Beautiful 2 B/R home, 5 minute walk to the beach
Make some memories at this unique and family-friendly custom built home. The master bedroom has a queen size bed and there is a full size bed in the second bedroom. This home, built in 2025, also includes a W/D, AC/Heat, and internet. Downtown you'll find restaurants, shopping and the pier. There is a swimming pool next door at Ne're Beach Family Campground free of charge and dedicated parking for 2 cars. Small dogs allowed. additional rentals: airbnb.com/h/19stjohn airbnb.com/h/21stjohn

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

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

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
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!

Drake's Island Beach Area Studio

Seaside Condo w/stunning views, 2 Queen sized beds
Other vacation rentals with a pool

Maine Coastal Village Getaway

Freshly Renovated, Family-Friendly Coastal Cottage

Pool and walking distance to beaches! Amenities!

Cozy Beach Cottage - Wells, ME

Secluded Rustic Log Cabin on Beautiful Frye Island

Portland Sweet Escape

Beautiful 2 bedrm cottage in Beach Dreams complex

Kennebunk's Charming Beach Home
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$45,654 GYD | G$47,530 GYD | G$49,197 GYD | G$52,116 GYD | G$48,364 GYD | G$55,243 GYD | G$72,962 GYD | G$72,962 GYD | G$41,693 GYD | G$43,361 GYD | G$46,904 GYD | G$48,572 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$10,423 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
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- Hampton Beach
- Sebago Lake
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