
Holiday rentals with a pool in Rockport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Rockport
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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.

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.

Relax in this 3BR “Gem of a Stay” •Pool •Grill
Feels like home from the moment you arrive—clean, cozy, and thoughtfully prepared for a relaxing stay. Enjoy a spotless space with everything you need, plus extra touches guests consistently rave about. Unwind in a peaceful setting and take advantage of the heated pool, BBQ grill, and outdoor space perfect for families after a day exploring the area. Nestled on a three-acre lot in a quiet neighborhood, this apartment is attached to the host’s home near the town of Gardiner.

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

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)

Three Sisters Retreat
Welcome to this spacious 4-bedroom ocean front retreat located in Surry, Maine! Perfect for families or groups, this comfortable home features a fully equipped kitchen, cozy living areas, plenty of room to relax and a pool! Enjoy the peace and beauty of coastal Maine while being just a short drive from Acadia National Park and Bar Harbor. Whether you're cooking, exploring, or simply unwinding, this home has everything you need for a great stay.

Port Cabin by Sea Maine
On the water, at the tip of Linekin Bay, sits this four-bedroom, two-bath cottage with a private swimming pool. The cottage has a modern, fully equipped kitchen (regular drip coffee maker) with a dining area that is perfect for gathering. The upstairs has two bedrooms with a queen-sized bed in each, while the downstairs has two double bunk bedrooms. There are two full bathrooms, one on each floor, and a spacious laundry room on the first floor.

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.

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.

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.

Ocean View Lawn Cottage - Newly Renovated 2024
Fully furnished ocean view cottage behind Fireside Inn Ocean's Edge in Belfast. Free wifi, use of the hotel's indoor pool, sauna & hot tub, washer & dryer access at the hotel, access to 9 acres of hotel grounds, and a rocky beach. Front Desk staffed 24/7. Linens and cookware included, but Housekeeping is NOT included. Pet friendly - fee separate from Airbnb price - $20 per pet per night, additional to be charged at check-in
Popular amenities for Rockport rentals with a pool
House rentals with a pool

Luxe Liberty: Getaway with Heated Indoor Pool!

Freeport Landing - Dog Friendly-Fall Favorite!

Kate's House at Spruce Harbor

Dana Cottage- Sebasco Harbor Resort

Peaceful 4 Bedroom Maine Retreat with Private Pool

Hemlock Creek

Peaceful home in Central Maine

4 Bedroom Riverside Home with Large Historic Barn
Apartment rentals with a pool

Lovely 2 bedroom updated riverside condo with pool

Tanager Cottage | 3BR + 2 Porches + Fireplace

Samoset Resort Oceanfront Condominium 816

Cardinal Cottage | 3BR + 3 Porches + Fireplace

Samoset Resort Oceanfront Condominium

Oriole Suite | Stone Fireplace + Woodland

Little Spruce Cottage | Wood Stove + Porch

Sunset A | Oceanfront King + Gas Fireplace
Other holiday rentals with a pool

Pebble Cottage- Sebasco Harbor Resort

Glamping Tent

RV Deluxe Rental

Water's Edge- Sebasco Harbor Resort

Geo Dome Deluxe

Dockside Cottage- Sebasco Harbor Resort

Historic Harpswell Cottage, Ocean Views

Cushman Cottage- Sebasco Harbor Resort
Quick stats about holiday rentals with a pool in Rockport

Total holiday rentals
Explore 30 holiday rentals in Rockport

Nightly prices starting at
Rockport holiday rentals start at € 69 per night before taxes and fees

Verified guest reviews
Over 240 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
30 of Rockport holiday rentals include wifi access

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

5 Average rating
Rockport stays are highly rated by guests – averaging 5 out of 5!
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- Acadia National Park
- Acadia National Park Pond
- Popham Beach, Phippsburg
- Pemaquid Beach
- Popham Beach State Park
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Rockland Breakwater Light
- Sand Beach
- Maine Maritime Museum
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Reid State Park
- Hollywood Slots Hotel & Raceway
- Bass Harbor Head Light Station
- Maine Discovery Museum
- Echo Lake Beach
- Belgrade Lakes Golf Club





