Holiday rentals with a pool in Rockland

4.95 out of 5 average rating, 620 reviews

Loft in Falmouth

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.

4.97 out of 5 average rating, 310 reviews

Home in Bangor

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

4.87 out of 5 average rating, 555 reviews

Flat in Cape Elizabeth

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

4.95 out of 5 average rating, 128 reviews

Home in Portland

"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 eateries and breweries. 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

4.97 out of 5 average rating, 419 reviews

Flat in Portland

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Mixing contemporary styling with an old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub or relax at a fire pit, our half-acre yard provides privacy for all guests. The fully private Apartment has an indoor gas fireplace, an elegant kitchen, dining, and living room. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

5 out of 5 average rating, 69 reviews

Flat in Portland

Luxe Eco Studio near Back Cove

2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

4.95 out of 5 average rating, 21 reviews

Flat in Damariscotta

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.

4.86 out of 5 average rating, 14 reviews

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.

4.98 out of 5 average rating, 254 reviews

Flat in Portland

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.

4.82 out of 5 average rating, 110 reviews

Home in Portland

There's No Place Like Home

Our home is filled with cozy spaces to relax and unwind. From the outside deck and pool to the quaint private bedrooms! This family friendly BnB provides a kitchen, dining room and two living areas for a vacation haven . This home has the feel of a true BnB, yet the entire space is dedicated to our guests. We are on site in our in-law quarters, so are close at hand for questions and help if needed. Our home is located in a convenient, quiet and safe neighborhood with off street parking.

4.92 out of 5 average rating, 142 reviews

Cottage in Surry

Loon Sound Cottage, On the Water

Sat - Sat. rental. Loon Sound Cottage, on beautiful Toddy Pond in Surry, is centrally located between Bar Harbor/Acadia & Blue Hill Peninsula. 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.

4.95 out of 5 average rating, 20 reviews

Home in Stonington

The Boathouse at Spruce Harbor

Come explore Spruce Harbor, a captivating oceanfront retreat 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 Boathouse, one of four private, charming, casual cottages on the compound. Jump into our tidal pool or launch a kayak from our beach area. Enjoy the serenity of both while still maintaining your privacy.

Holiday rentals for every style

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Popular amenities for Rockland rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 28 reviews

Home in Bangor

New Boho Cape with Pool! Fenced yard, pet friendly

CindyRating, 5 stars1 month ago

Thank you Christina! Great weekend stay for UMaine graduation. Great location from campus and stores for the things we forgot (haha).

4.91 out of 5 average rating, 75 reviews

Home in Liberty

Luxe Liberty: Getaway with Heated Indoor Pool!

WendyRating, 5 stars1 week ago

this was the 3rd time our family has stayed,again we had a fantastic time! We chose to return due to the great space, a fabulous indoor pool, great kitchen and an amazing view. Great attention to details, comfortable for large families or groups and peaceful for just 2.

Home in Old Orchard Beach

4.82 out of 5 average rating, 11 reviews

Oceanfront Cottage 1

LoganRating, 5 stars3 months ago

We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!

4.86 out of 5 average rating, 7 reviews

Home in Washington

House in the woods

SavannahRating, 5 stars6 months ago

Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

MollyRating, 5 stars11 months ago

Home in Harpswell

Whispering Winds Cottage, Offering Ocean views

Spent a wonderful week with my family, feel honored to be the very first guests! We have already asked to come back next year, I cannot recommend this place enough! The view from the porch, the pool, the greenery all around, was just perfection. My kids also loved the main hall where we could play ping pong, pool and shoot baskets. We used the tennis court, had dinner at the food hall and loved the location to visit all our favorite Maine spots like Popham beach, Reid state park and all surrounding islands have to offer. Sheri was incredibly responsive, kind and helpful as we needed through out the stay. The house had all necessary items to move right in with groceries! Can’t wait to return.

4.97 out of 5 average rating, 29 reviews

Home in Trenton

Acadia get away.! With pool and hot tub

JanelleRating, 5 stars8 months ago

I recently stayed with my family at this incredible Airbnb that exceeded all my expectations. This property offered a hot tub, a pool table, and a level of privacy and tranquility that made for a truly relaxing getaway. One of the highlights of our stay was being able to watch the northern lights from the hot tub – it was absolutely magical. We spent a week in Acadia, and the location was perfect, just 15-20 minutes from Bar Harbor or the nearest town. The hosts were very responsive, and the place was fantastic for families, being both kid and pet friendly. It was a week filled with unforgettable moments, and I can't recommend this place enough!

4.7 out of 5 average rating, 47 reviews

Home in Tremont

Large MDI house w/pool perfect for groups+families

MauraRating, 5 stars8 months ago

We had a great stay at this house! Plenty of beds for everyone. Convenient to get to Acadia and bar harbor with a short drive!

5 out of 5 average rating, 11 reviews

Home in Portland

The Hill's on Buttonwood

DanielRating, 5 stars7 months ago

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

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Apartment rentals with a pool

4.78 out of 5 average rating, 9 reviews

30 second walk to Beach- Pool-Outdoor Shower

AleeshaRating, 5 stars11 months ago

place is perfect for my parents who are older and can easily get in and out of the condo. fellow people at the condo are nice and respectful.

4.91 out of 5 average rating, 11 reviews

Grand Victorian Ocean Rentals Oob310

LisaRating, 5 stars10 months ago

Beautiful, spacious condo. Jenny was clear with all instructions. Location was central to things to do and right on the beach. It is a little pricey but worth it.

5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars11 months ago

This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!

4.81 out of 5 average rating, 48 reviews

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

CaseyRating, 5 stars9 months ago

Located right in the middle of all the action! Perfect beach access and my kids had a blast at palace playland. Unit had everything we needed.

5 out of 5 average rating, 4 reviews

Just steps to the beach

GingerRating, 5 stars10 months ago

This was exactly what we needed! What a perfect little place. It’s a 30-second walk to the beach and an easy 1.3 mile walk to the downtown area. We walked everywhere and clocked 15 miles per day between the beach stroll in the AM, scooter/jog with my kids to the arcade at 10am, and afternoon/evening walks to the nonstop carnival. The apartment has everything you need and the kitchen is so well stocked with the basics. Such a great place! Perfect for a family visit to the beach. Also, I was surprised by how clean and safe the downtown felt. Ideal for families and young kids. Thank you, Julie!

MargaretRating, 5 stars30 months ago

Ocean View Studio Beach Condo

It was such a cozy, wonderful condo with ocean sounds and breezes right from the front door. Neighbors very kind and welcoming; never felt like a stranger from the first day! Although just a studio, quite spacious and very comfortable even when my husband and child came to visit! David always responded to any questions rather about the condo, condo building, or just a good place to eat! Just a lovely all around stay! All my classmates were jealous! :)