
Vacation rentals with a pool in Rockland
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Top-rated rentals with a pool in Rockland
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.

Cozy, fun, 3 bedroom home with a pool and Hot Tub.
3 miles from concerts. Relax by your own, personal pool and roast marshmallows by the fire in the private back yard. Then come inside and enjoy a foosball game at the living room table This is a peaceful and centrally-located place, in a safe neighborhood. It’s about 5 minutes away from everything in Bangor, and a little over an hour away from the Bar Harbor area. security deposit required The entire house is available to you, including the yard, fire pit and pool out back. The pool is unheated

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

Loon Sound Cottage, On the Water
Loon Sound Cottage, on beautiful Toddy Pond in Surry, is centrally located between Bar Harbor/Acadia & Blue Hill. Come and enjoy the peace and tranquility of a lakeside oasis while just being a short distance from many sites of interest. Visit nearby Castine, Blue Hill, Bar Harbor, and Acadia National Park. Hear the loons at night, kayak to beaver cove and see an eagles nest. A tranquil and peaceful setting. A perfect balance of rest and adventure. We prefer Sat-Sat. rental but flexible.

Maine Hacienda w/hot tub & seasonal pool
Our renovated suite at the foot of Deering Highlands is a 10 minute drive to downtown Portland. A cozy, quiet, modern space with a maritime edge. A short walk to Woodford’s corner and Forest Ave - home to many restaurants & coffee shops. The space includes a seasonal pool and year-round hot tub. Ideal for singles, couples or couples with one or two small children. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.

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

Large private area, close to Rockland
Quiet and private neighborhood. Perfect for family or group getaways. Kid friendly. One mile from public ocean access, (WesKeag River) Five miles from downtown Rockland, and just minutes from downtown Thomaston. Three beautiful beaches within five miles. It’s the perfect place to stay while exploring the coastline, enjoying the downtown shops and restaurants, hiking and exploring the nearby cultural attractions. Two night minimum.

Faith Lane with community pool
Newly built open concept with gorgeous quartz counters and vanities. 4 spacious bedrooms so large parties will be very comfortable. Deck with gas grill, table and chairs, and kids picnic table. Community pool and only minutes drive to the beach and pier. Located in the brand new Church Street Station community. The beach trolley stop at Elmwood and Marcotte Motors Motel can take you right to the beach.

Luxe Liberty: Getaway with Heated Indoor Pool!
Looking for a beautiful, remote getaway? This spacious 6-bedroom, 3-bath home offers room to relax, gather, and make memories. Liberty, ME is 16 mi to Belfast • 20 mi to Camden • 53 mi to Bangor & Airport • 70 mi to Bar Harbor & Acadia National Park Important things to note: Base pricing includes up to 8 guests Additional guests: $75/p/n Bunk rooms are NOT available for groups of 8 or fewer guests
Popular amenities for Rockland rentals with a pool
House rentals with a pool

Coastal Retreat with Pool and Cheerful Vibes

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

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

House in the woods

Designers Dream Home with Pool!

Dog Friendly Midcoast Cape

The Getaway - A River Paradise

Ocean View Retreat with Heated Pool / Hot Tub
Condo rentals with a pool

30 second walk to Beach- Pool-Outdoor Shower

Stars And Stripes

Two-bedroom condo near Acadia National Park, Maine

LUXURY OCEANFRONT CONDO Best Location on the beach

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Condo in Old Orchard Beach

RARE 3 Bedroom at the Resort at Goose Rocks Beach

Lovely 2 bedroom riverside condo with pool
Other vacation rentals with a pool

Lovely 1 bedroom loft above garage, with big yard.

Cottage by the sea

Spacious 5BR Cottage w/Pool, Water & Resort Access

Beautiful 2 B/R home, 5 minute walk to the beach

Peaceful, Spacious Lodge with Golf & Sunset Views

Kennebunk's Charming Beach Home

Saco Cozy Cottage! Minutes From Old Orchard Beach!

Atlantic Ocean Suites - Sand Castle Suite 7
Quick stats about vacation rentals with a pool in Rockland

Total vacation rentals
Explore 30 vacation rentals in Rockland

Nightly prices starting at
Rockland vacation rentals start at G$18,836 GYD per night before taxes and fees

Verified guest reviews
Over 90 verified reviews to help you choose

Wi-Fi availability
30 of Rockland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Rockland rentals

4.9 Average rating
Rockland stays are highly rated by guests—averaging 4.9 out of 5!
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- Acadia National Park
- Acadia National Park Pond
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Sand Beach
- Maine Maritime Museum
- Farnsworth Art Museum
- Rockland Breakwater Light
- Bass Harbor Head Light Station
- Moose Point State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Reid State Park
- Camden Hills State Park




