
Vacation rentals with a pool in Old Orchard Beach
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Old Orchard Beach

Total vacation rentals
Explore 150 vacation rentals in Old Orchard Beach

Nightly prices starting at
Old Orchard Beach vacation rentals start at G$10,456 GYD per night before taxes and fees

Verified guest reviews
Over 1,730 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
150 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

4.8 Average rating
Old Orchard Beach stays are highly rated by guests—averaging 4.8 out of 5!
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.

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)

"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

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.

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.

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!

1 mile to OOB pier | Outdoor fire pit | Game room
Welcome to your next summer vacation at this OOB beach getaway! This newly built 2-bedroom home is located in a quiet, beautifully maintained community with a seasonal pool, and it’s only a 5-minute drive (or 1 mile walk) to the beach. Ideal for family vacations, this beautiful home blends modern comfort with easy access to everything the area has to offer. Even better—the beach trolley stop is right around the corner, giving you a quick, car-free ride straight to the ocean.

Steps to Beach, Pier, Park | Condo with Pool • 6
Welcome to Sunset Suites, your ideal getaway in the heart of Old Orchard Beach! Each updated 1-bedroom suite features a kitchenette with a sink, fridge, a private bathroom with a shower, one comfortable queen bed and a pull out twin sofa bed. Enjoy our on-site pool or take advantage of the fantastic location: adjacent to a park with tennis courts, and just a short stroll to Playland Adventures, the famous pier, and the beach. Experience your perfect home away from home!
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

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*

Designers Dream Home with Pool!

Maritime Meadows – Charming Resort-Style Home!

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

30 second walk to Beach- Pool-Outdoor Shower

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Lovely Ogunquit Studio, Pools, Walk to Everything!

LUXURY OCEANFRONT CONDO Best Location on the beach

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

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Our Happy Place!

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

55+ Seniors Only -Pet Friendly -Safe -Clean Unit

Cottage by the sea

Beach Bliss

Walk to Wells Beach! July dates available!

Luxury Condo with a Pool in wonderful OOB!

Saco Cozy Cottage! Minutes From Old Orchard Beach!

Ocean Beach Cottage Wells, ME

Saco/Old Orchard Beach Cottage
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$42,241 GYD | G$62,526 GYD | G$79,882 GYD | G$52,279 GYD | G$48,515 GYD | G$55,416 GYD | G$73,190 GYD | G$73,190 GYD | G$41,823 GYD | G$43,496 GYD | G$47,051 GYD | G$48,724 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 |
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