Holiday rentals with a pool in Cumberland

4.95 out of 5 average rating, 621 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.

4.92 out of 5 average rating, 212 reviews

Chalet in Bartlett

*Chalet in the Sky|NorthConway+StoryLand|Outlets

This stunning 2-bedroom chalet, styled by the Homme team, is the perfect Family and Friends retreat! Nestled in North Conway’s White Mountains, down the street from Story Land and the Outlet shopping plaza. This home is ideal for families, friends, or ski lovers. Enjoy breathtaking views, free onsite parking, modern amenities, and easy access to top attractions for a trip to remember! 🌿✨ 🎢 Story Land - 10 Min ✨ Santa's Village- 20 Min 🌿 Diana’s Baths - 10 Min 🚠 Mt. Washington Auto Rd - 35 M

Apartment in Cape Elizabeth

4.87 out of 5 average rating, 557 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

4.95 out of 5 average rating, 129 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

5 out of 5 average rating, 69 reviews

Apartment 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!

5 out of 5 average rating, 15 reviews

Home in Scarborough

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches

Experience the luxury of your own solar-powered, eco-friendly spa getaway in Maine! Enjoy a private spa in a four-season sunroom, featuring a heated indoor fitness pool and hot tub. Boost your immune system with hydrotherapy, then step outside to a sauna and fire pit -a truly indulgent retreat. Plus, we’re just minutes from beaches, lighthouses, and Portland’s Old Port! Enjoy complimentary access to beautiful local beaches and parks with our included beach pass—yours to use during your stay!

4.98 out of 5 average rating, 254 reviews

Apartment in Portland

Maine Hacienda w/hot tube & 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.

4.97 out of 5 average rating, 195 reviews

Townhouse in Bartlett

3 Bears Glen- Across St from Story Land, Pool & AC

Welcome to Three Bears Glen! A cozy condo is located right across the street from StoryLand and Living Shores Aquarium! This 2 Bedroom 1st floor end unit condo is the perfect getaway. This family friendly home features a private entrance, fully equipped kitchen, A/C, Wi-Fi, 3 Roku enabled TVs, games(adults & kids), washer/dryer & patio seating. Golf our 9 hole course located right outside the front door. Enjoy the outdoors at the pool, playground, hiking or mountain biking near the condo.

4.9 out of 5 average rating, 308 reviews

Home in Harrison

Riverfront Luxury in the woods, Million $ Views.

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

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.

4.96 out of 5 average rating, 514 reviews

Guesthouse in Portland

Romantic Bungalow with Hot Tub, Pool & Parking

The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

4.93 out of 5 average rating, 106 reviews

Guest suite in Standish

Steep Falls Escape, river & falls just steps away

Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Cumberland rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 34 reviews

Home in Biddeford

JennaRating, 5 stars6 days ago

The house was spotless and centrally located for what we wanted to do in southern Maine. It was well stocked with quality toilet paper, napkins and Kleenex. We had plenty of towels for the hot tub and pool. It is updated and well taken care of. The hosts were extremely helpful and we didn’t see them at all, so the place felt very private. This was an amazing house and our kids had so much fun in the pool and playing corn hole on the large deck. Would recommend this house for families and couples in a heartbeat!

5 out of 5 average rating, 53 reviews

Home in Wells

2BR, Sea & Relax w/ Wells Reserve View

KatherineRating, 5 stars6 days ago

Cottage 2 br, well equipped kitchen and nice extra porch enclosed and furnished beachy decor. Backyard comfortable adirondack chairs for sitting. Near to beach with free parking if spots are available. plenty of restaurants and grocery nearby. Last cottage in the row and was quiet. Pool and hot tub on property. Would rent again.

4.9 out of 5 average rating, 202 reviews

Home in Bartlett

Fireplaced Mountain King Suite w/Hot Tubs & Pools

JenniferRating, 5 stars6 days ago

Loved staying in this room! Perfect for families with small kids, right across from the playground and so close to story land. Had a blast and would def stay here again!

5 out of 5 average rating, 4 reviews

Home in Arundel

Spectacular 3 Bed Resort Cottage

JaimeRating, 5 stars1 day ago

This cottage in Arundel was just perfect! Beautiful, private, quiet setting, and just a short drive to all the best beach towns! We absolutely loved everything about it! Jaime & Susan

4.89 out of 5 average rating, 124 reviews

Home in Barnstead

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

AndresRating, 5 stars1 month ago

The house is beautiful and the views are just breathtaking. From inside the house, you get a beautiful view of the lake and then the porch is amazing. You can kayak, use the paddle board or use the canoe. You can also sit by the lake and enjoy the campfire. The surroundings are very beautiful and peaceful. The host is very responsive, solved all our doubts and was flexible with us during check-in and check-out, which we appreciated very much. At check-in, we were greeted by a great bottle of wine and chocolates, which was a great touch. The house also has a ping pong table, books to read and board games. The kitchen was well stocked with the basics. We had an amazing stay, we highly recommend this property :)

4.96 out of 5 average rating, 28 reviews

Home in Kennebunkport

Lovely Beach house in GRB - Heated pool!

CharlotteRating, 5 stars3 weeks ago

We absolutely loved our stay! The home is gorgeous, light and airy, and so comfortable for our group! You can't beat the location across from the beach and quiet street for walking. The pool and hot tub were also so nice. We would highly recommend and would love to stay there again!

4.92 out of 5 average rating, 13 reviews

Home in Saco

Cottage ten minutes from beach

VincentRating, 5 stars4 weeks ago

Great place to stay! Clean and comfortable. Excellent location, close to many restaurants, and other activities!

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

Show all

Condo rentals with a pool

4.85 out of 5 average rating, 188 reviews

Condo in Wells

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 weeks ago

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

4.84 out of 5 average rating, 358 reviews

Condo in Bartlett

Quiet Condo Close to Shopping and Attractions

KeighleyRating, 5 stars4 weeks ago

Amazing place! Clean, lots of amenities, and the place had all the basics you could need! I will definitely be referring friends and returning for future trips!

4.93 out of 5 average rating, 201 reviews

Condo in Bartlett

Bartlett Condo; Great Views, Resort Access

BrianRating, 5 stars3 months ago

Would highly recommend this place if you’re in the Conway area or would like to explore all that this area has to offer. Very easy to get to and it’s in a perfect location with great views.

4.99 out of 5 average rating, 143 reviews

Condo in Bartlett

KimBills’ on the Saco

SaraRating, 5 stars3 days ago

We had a great stay to celebrate our son’s 5th birthday at Storyland. The condo was comfortable and well organized with a great outdoor patio space. We had a wonderful experience!

4.95 out of 5 average rating, 102 reviews

Condo in Wells

Relaxing Beachside Condo with Pool at Wells Beach

MaryRating, 5 stars1 month ago

Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.

4.76 out of 5 average rating, 134 reviews

Condo in Wells

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars4 weeks ago

Great place to stay for our family of 4. I asked for 3 beds and that request was made possible. I enjoyed the area and it was quiet and peaceful place to rest after walking around the beaches and or state parks. Amenities were very good and communication with the check in team was excellent.

4.96 out of 5 average rating, 111 reviews

Condo in Conway

Cozy, clean, 2nd floor condo in Conway, NH!

RachelRating, 5 stars5 months ago

A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!