Vacation rentals with a pool in Rockland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Rockland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.
Apartment in Cape Elizabeth
4.87 out of 5 average rating, 582 reviews

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

Top guest favorite
The charming exterior of a cottage is highlighted by blue wood siding and yellow trim. A flower bed with colorful blooms lines the gravel path leading to the entrance. A decorative birdhouse rests on a tree nearby, complementing the natural surroundings.
Cottage in Surry
4.93 out of 5 average rating, 155 reviews

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.

Top guest favorite
A two-story building is featured, with a spacious balcony providing seating options. Large windows on the upper level allow ample natural light. The ground floor has two garage doors, and the exterior is finished in white siding, set against a backdrop of trees.
Guest suite in Pittsfield
4.97 out of 5 average rating, 36 reviews

Angel Mist Retreat Garage Apartment

Looking to get away from the hustle and bustle. You have found it! Watch for wildlife, while sipping coffee from the balcony of this cozy and stylish walkup apartment located in central Maine just minutes from I-95 between Augusta and Bangor. Ideal location for professionals, couples and parents traveling into Maine who enjoy solitude, but appreciate the comforts of modern amenities. Includes two king beds, stocked kitchen, large dining table, wifi, balcony off livingroom and master bedroom.

Superhost
The living area presents a blend of comfort and style, featuring a spacious gray sofa complemented by a wooden coffee table. A stone fireplace serves as a focal point, while built-in shelves display curated items. Natural light fills the space through large windows, enhancing the inviting ambiance.
Home in Lincolnville
4.88 out of 5 average rating, 16 reviews

Coastal Retreat with Pool and Cheerful Vibes

Indulge in a serene getaway at this 3-bedroom, 2-bath home that boasts ample space for relaxation & entertainment. The kitchen is fully equipped, the common areas provide an ideal setting for making memories. Within the community, this stunning abode offers access to tennis courts & a swimming pool, as well as scenic walking trails along the river. The home is conveniently located near Lincolnville Beach & Camden. Experience your own slice of paradise, where relaxation & rejuvenation await.

Top guest favorite
A spacious blue house is set against a backdrop of lush green grass and trees. The property features a landscaped front area with various shrubs and stone walls, inviting outdoor seating arrangements, and a clear sky above, enhancing the serene atmosphere.
Home in Liberty
4.89 out of 5 average rating, 93 reviews

Luxe Liberty: Getaway with Heated Indoor Pool!

Please be sure to read ALL listing details before booking. Looking for a beautiful remote getaway? This 6 bedroom, 3 bath home has plenty of room for everyone. We are located in Liberty, Me but only: 16 mi to Belfast 20 mi to Camden 53 mi to Bangor & Airport 70 mi to Bar Harbor & Acadia National Park The opportunities for making memories are ENDLESS here. Let us be your new favorite vacation rental! *Pricing is based on 8 guests. Add’l guests $75/p/night. Pool heated Sept/Oct-May.

Guest favorite
A spacious house is nestled among lush green trees, set back from a winding driveway. Bright sunlight filters through the leaves, and well-maintained gardens are visible in the foreground, with a natural rock formation enhancing the landscape.
Home in Sidney
4.82 out of 5 average rating, 17 reviews

Peaceful full home The Maine Experience

This family-friendly retreat in Sidney, Maine offers the perfect mix of comfort and nature. Set on a large private property with forests, open skies, and nearby lakes, it’s a peaceful escape with plenty of space to relax. Enjoy modern, upscale amenities—including a sparkling pool and big outdoor areas—great for families, groups, or anyone visiting nearby colleges like Colby or Thomas. Whether you're here for a campus visit or a quiet getaway, you’ll feel right at home.

Superhost
An aerial view captures a spacious property with a well-maintained lawn, a large inground pool, and a sunlit deck. The two-story house is complemented by manicured landscaping and treed surroundings, creating a serene environment. A small shed is positioned nearby, enhancing the outdoor space.
Home in Wilton
5 out of 5 average rating, 3 reviews

The Calixte Retreat, Maine.

Experience tranquility in this sophisticated setting, situated on a hilltop and surrounded by rolling fields, providing idyllic views and stunning panoramas of the far-off horizon. Summer days can be spent lounging on the spacious deck after swimming laps in the 20 x 40 inground pool or playing golf at the nearby Wilson Lake Country Club. Winter months offer easy access to skiing at Titcomb Mountain, just 10 minutes away, or Spruce Mountain Ski Slope, 20 minutes away.

Superhost
Cottage in Belfast
4.74 out of 5 average rating, 27 reviews

Oceanfront Shore Cottage - Newly Renovated

Fully furnished cottage in front of Fireside Inn & Suites, right at the ocean's edge. Ocean view, utilities (and plowing) included. Includes wifi, use of hotel indoor pool, sauna & hot tub, access to 9 acres of hotel grounds and rocky beach front. Front Desk staffed 24/7. Washer/dryer (in basement, entrance through outside door underneath deck), linens and cookware included but Housekeeping is NOT included. Pet friendly with additional cleaning fee.

Guest favorite
A gravel driveway leads to a white house nestled among tall trees. Lush greenery surrounds the area, creating a serene atmosphere. A pathway connects the house to the driveway, with steps visible leading up to the entrance.
Home in Washington
4.95 out of 5 average rating, 19 reviews

House in the woods

Relax with the whole family at this peaceful place to stay. Quiet neighborhood. Open concept with pool and hot tub, big open lawn. Master bedroom-Queen Second bedroom- Full/Double Living room -large sectional Queen air mattress Possible sleep 8 The address is 34 Homestead Rd , but this app has it as fire road - it is the same ! I do have a business down in basement -hair salon- not typically an issue ( I try not to be open when I have guests)

Guest favorite
A heated saltwater pool is visible in the foreground, surrounded by wooden decking. Lush greenery and colorful flowering plants frame the space, leading to a picturesque ocean view in the distance. The scene captures the tranquility of the landscaped garden.
Home in Rockport
4.95 out of 5 average rating, 61 reviews

Ocean View Retreat with Heated Pool / Hot Tub

Newly renovated, heated heatsaltwater pool with ocean views overlooking the Rockport harbor, open all winter. Fireplace and heated floors. Three bedrooms and four baths. Gourmet Kitchen. 2,900 square feet, in the heart of Rockport Village, walk to the harbor and local restaurants through private lighted path and gardens. Huge deck. Walk down to the harbor, restaurants, and a coffee shop right in front of the house. Fast internet. No TV.

Guest favorite
Home in South Thomaston
4.94 out of 5 average rating, 106 reviews

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.

Superhost
A serene view of Penobscot Bay at sunrise, featuring a pastel sky in shades of pink and purple. Small boats are visible on the water, while a lighthouse stands on the shoreline. A grassy area has benches and picnic tables, inviting outdoor enjoyment.
Apartment in Rockland
5 out of 5 average rating, 4 reviews

Heart of Rockland Maine

Located in downtown Rockland Maine. Wake up to the most spectacular sunrise over Penobscot Bay. 3 Decks overlooking Main Street, Harbor Park and Penobscot Bay. Take in the North Atlantic Blues Festival and Maine Lobster Festival from the deck of this unit. The 2 level unit in located on the 5th floor. Full kitchen and use of common indoor pool. Located on Main Street and within walking distance to shops, museums and restaurants.

Popular amenities for Rockland rentals with a pool

Quick stats about vacation rentals with a pool in Rockland

  • Total vacation rentals

    Explore 40 vacation rentals in Rockland

  • Nightly prices starting at

    Rockland vacation rentals start at € 60 per night before taxes and fees

  • Verified guest reviews

    Over 100 verified reviews to help you choose

  • Wi-Fi availability

    40 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!

Destinations to explore

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  4. Knox County
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