Vacation rentals with a pool in Rockport

4.92 out of 5 average rating, 146 reviews

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

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.

4.95 out of 5 average rating, 60 reviews

An outdoor space is highlighted by a heated saltwater pool surrounded by a wooden deck. Comfortable seating options are arranged nearby, complemented by a large umbrella for shade. Lush greenery and a mature tree provide a natural backdrop, enhancing the inviting atmosphere.

Home in Rockport

Ocean View Retreat with Pool / Hot Tub

Newly renovated, saltwater pool with ocean views overlooking the Rockport harbor, with a vast garden. Fireplace and heated floors. Three bedrooms and four baths. Gourmet Kitchen. 2,500 square feet, in the heart of Rockport Village, walk to the harbor and local restaurants through the winding private path and gardens. There is a huge deck, a landscaped garden, and outdoor furniture. Walk down to the harbor, restaurants, and a coffee shop right in front of the house. Fast internet. No TV.

Apartment in Damariscotta

A well-equipped kitchen and dining area are showcased, featuring modern appliances and light cabinetry. A spiral staircase leads to additional spaces, while a small dining table is accompanied by three stools. A television is mounted on the wall, and natural light enhances the warm atmosphere.

4.96 out of 5 average rating, 26 reviews

2 Bedroom new renovation Condo/Pool/ River Access

Forget your worries in this spacious and serene space. Plenty of room for 4 with all new furniture, appliances, rugs and linens. An amazing space for a weekend or a month. Enjoy all the comforts of home in this special beautifully appointed 2 bedroom/3 bed private. Easy access to grocery, YMCA, Round top Ice Cream and some of the best restaurants in Damariscotta. Take in a nature hike to the Damariscotta River from your private path in the backyard. Free parking and beautiful pool in summer.

4.87 out of 5 average rating, 15 reviews

A swimming pool is surrounded by paved decking, with several lounge chairs positioned throughout. A green umbrella offers shade near the poolside, and lush landscaping with trees and flowering plants is visible in the background, complemented by a clear blue sky.

Home in Lincolnville

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.

4.91 out of 5 average rating, 81 reviews

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

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.

5 out of 5 average rating, 3 reviews

A charming, two-story yellow cottage features a welcoming front porch with comfortable seating. Large windows allow natural light to fill the space, and a well-kept yard surrounds the home. Nearby, an American flag gently sways, complementing the tranquil rural setting.

Home in Harpswell

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

Escape to Whispering Winds Cottage, a charming 5-bedroom retreat in Harpswell’s historic Auburn Colony. Nestled on 20 acres with ocean views, pool access, and timeless character, this spacious cottage offers modern comforts, privacy, and direct water access, if you'd like to bring along your kayaks! Enjoy community dinners, games, and relaxing on the porch as the sun sets. A perfect blend of history, nature, and coastal Maine charm — ideal for families or groups

4.93 out of 5 average rating, 30 reviews

A clear view of a swimming pool is presented, surrounded by a white picket fence. Lush greenery serves as a backdrop, with patches of decorative stones and blooming flowers alongside the grass and concrete patio.

Loft in Searsport

Lovely 1 bedroom loft above garage, with big yard.

Looking for a central location on the coast of Maine? This lovely loft is within 2 miles of Swanlake and the boat landing! We are within 45 mins to all the surrounding towns, Like Bangor, Ellsworth, Blue Hill, Acadia And Camden all Beautiful places to visit during your stay. We are very secluded so don't be surprised if you see a deer here or there. Come stay with us and enjoy our lovely loft for some quiet relaxation and a dip in the pool.

4.96 out of 5 average rating, 97 reviews

A spacious yard features a small above-ground pool and a playground set among trees. The two-story house with a large driveway is seen in the background under clear blue skies, creating a welcoming outdoor space suitable for families.

Home in South Thomaston

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.

4.72 out of 5 average rating, 18 reviews

A charming two-story home is surrounded by lush greenery and vibrant flower beds. The exterior features a shingled facade and multiple windows that invite natural light. A large tree provides shade, framing the home’s picturesque setting within a well-kept garden.

Apartment in Winthrop

Cozy Apartment with In-Town Convenience

This is a 2nd story apartment above our garage with a small but fully equipped kitchen, full-size refrigerator, microwave, electric stove/oven, double sink (no dishwasher), a plentiful supply of dishes, tableware, cookware, new queen bed, bathroom with shower, hair dryer, bathroom necessities, living area with couch/queen size futon, Smart TV with Apple TV, Fubo TV, wifi, iron & ironing board. Our preference is for long-term renters.

4.94 out of 5 average rating, 16 reviews

A tranquil ocean water pool is visible at dusk, framed by smooth granite rocks. The water reflects the soft pink and purple hues of the sunset sky. Lush greenery borders the area, enhancing the serene coastal environment.

Apartment in Stonington

The Carriage House at Spruce Harbor

Come explore the captivating Spruce Harbor on Deer Isle, where retreating glaciers left behind a beautiful landscape of spruce-clad islands, rocky shorelines, undulating countryside and picturesque beaches. A gently, winding, wooded lane carries you to the 'Carriage House,' which is one of four private, charming, casual oceanfront cottages on the compound. Jump into our “ocean water pool” or launch a kayak from our beach area!

5 out of 5 average rating, 12 reviews

The exterior of the property features a classic white façade with multiple gabled roofs and a porch adorned with rocking chairs. Lush greenery surrounds the house, complemented by flowering plants along the pathway leading to the entrance.

Home in Newcastle

The Flying Cloud

Gather in Comfort at The Flying Cloud Visiting for an event or getaway? The Flying Cloud offers space for your group—where everyone gets their own bedroom and bathroom! Relax in the swim spa and hot tub, share meals at the 14-person dining table, and enjoy games, TVs, and quiet spaces. Just a 5-minute walk to downtown Damariscotta, you’re close to shops, dining, and waterfront views. Book your stay today!