
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.

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.

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.

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.

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)

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.

Gorgeous house with a view
This house is situated on the grounds of Seascape, a newly renovated motel located in Belfast, ME. The whole group will enjoy easy access to everything from this centrally located place. This beautiful home consists of 2 bedrooms and a day bed in the great room. There is plenty of room for gathering and is perfect for the little ones because of the fenced in play area. The perfect family getaway!

Cozy Studio Flat, Belgrade Lakes Region
Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.
Popular amenities for Rockport rentals with a pool
House rentals with a pool

Cove House with Private Pool, Ocean Views, Family

The Boat House

Resort style, family friendly getaway!

Freeport Landing - Dog Friendly-Fall Favorite!

Ocean view- golf course 3 bed

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

Hemlock Creek

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

Cozy Forest Cottage | Stone FP | No Hidden Fees

Lovely 2 bedroom riverside condo with pool

Woodland Cottage | Fireplace | No Hidden Fees

Oceanfront Multi-level Condo with Prime Amenities

Samoset Resort 1br suite, Friday check-in

Samoset Resort 2br Suite, Saturday Check-In

Oceanfront King Rm | Sunset View | No Hidden Fees

Samoset-Affordable Luxury
Other holiday rentals with a pool

Captain's Cottage

Sunrise Shores Cabin 08

Mariner's Rest Cabin 05

Gulls Nest Cabin 03

Ocean Kiss Cabin 09

A Place to Be Crows Nest Mt Vernon Me

Peaceful Waterfront Apt w/ Deck, 22 Mi to Portland

The Sylvan
Quick stats about holiday rentals with a pool in Rockport

Total holiday rentals
Explore 50 holiday rentals in Rockport

Nightly prices starting at
Rockport holiday rentals start at $107 AUD 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 and kid-friendly amenities

Wi-Fi availability
50 of Rockport holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Rockport rentals

4.9 Average rating
Rockport stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with pools United States
- Acadia National Park
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- Northeast Harbour Golf Club
- Pemaquid Point Lighthouse
- Belgrade Lakes Golf Club
- Acadia National Park Pond
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Sandy Point Beach
- Hunnewell Beach
- Sand Beach
- Bear Island Beach
- Maine Maritime Museum
- Lighthouse Beach
- The Camden Snow Bowl
- Eaton Mountain Ski Resort
- Brunswick Golf Club
- Wadsworth Cove Beach
- Kebo Valley Golf Club
- Spragues Beach
- Farnsworth Art Museum




