Vacation rentals with a pool in Cumberland

4.95 out of 5 average rating, 617 reviews

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

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, 209 reviews

A covered patio area is shown with bright red chairs facing a panoramic view of lush green mountains under a clear blue sky. The surrounding landscape features a mix of greenery and distant mountain peaks.

Chalet in Glen

*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

A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.

4.87 out of 5 average rating, 553 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, 126 reviews

Home in North Deering

"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

Apartment in North Conway

A view of the pool area showcases a refreshing swimming pool, surrounded by inviting green lawns and a white picket fence. Picnic tables and lounge chairs are positioned nearby, offering plenty of outdoor space for relaxation. Several charming cabin-style buildings are visible in the background.

4.89 out of 5 average rating, 333 reviews

NoCo Village King/Jacuzzi.

Welcome to Village Place at the Eastern Slope Inn! Must be 21 to check-in, $40 authorization taken at check-in (not an actual charge), no cats. IF YOUR PUP IS JOINING YOU, please provide advanced notice, a $25/night pet fee for the first 4 nights, RABIES RECORDS, and a crate if you must leave them behind. One dog is permitted per room, no cats, thanks for understanding. Located halfway between The Eastern Slope Inn and Cranmore Mountain, this second floor unit is walking distance to it all!

5 out of 5 average rating, 7 reviews

A cozy bedroom features a spacious bed dressed in fresh white linens with a nautical-themed throw blanket. Two framed black-and-white photographs are displayed above the bed. Soft lighting is provided by two bedside lamps, creating a calm, restful environment.

Apartment in Wells

Everything's "Well Ashore"- 1 mile to Wells Beach!

Welcome to 'Well Ashore', a charming 1-bedroom, 1-bathroom condo just 1 mile from the breathtaking Wells Beach- One of Maine's 7 -mile pristine sandy beaches. Ideal for couples or small families, this cozy retreat features a serene, nautical-inspired ambiance perfect for relaxation. Our condo is 4 miles from The Marginal Way, one of New England's most cherished coastal walks. This 1.25 mile scenic path offers stunning ocean views, plentiful benches, and an easy access to downtown Ogunquit.

4.98 out of 5 average rating, 253 reviews

The exterior of a charming three-story building is visible, adorned with a warm stucco finish. A seasonal pool in the foreground reflects the structure. Various patio seating options and an umbrella area create an inviting outdoor space, complemented by lush greenery in the surrounding garden.

Apartment in Rosemont

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.

4.9 out of 5 average rating, 307 reviews

An aerial view showcases an A-frame cabin nestled among greenery, surrounded by trees and a tranquil pond. A winding path leads to the cabin, highlighting the seamless integration of nature and architecture. The setting reflects a peaceful and private retreat.

Home in Harrison

EPIC VIEWS, Hot Tub, Pond, River, 14 Acres A Frame

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!

4.94 out of 5 average rating, 148 reviews

A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.

Cottage in Wells

Cozy Cottage with Ocean Views, Wells Maine

Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

4.82 out of 5 average rating, 110 reviews

A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.

Home in Deering Center

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.

An inviting in-ground pool is surrounded by a spacious patio, offering numerous lounge chairs for relaxation. Lush green lawns and trees frame the pool area, while buildings are visible in the background, contributing to a serene outdoor setting.

4.92 out of 5 average rating, 461 reviews

Across from Storyland & in the Heart of the Mtns

Welcome to the perfect getaway condo in the heart of the mountains! Our 2 BR home is directly across from Storyland, close to major ski resorts, minutes from downtown North Conway, &located on a Country Club where you can enjoy golf and the in-ground pool (typically June-August) making this the perfect NH getaway. The condo has a private entrance, a fully equipped kitchen, grill, cable & WiFi and video & board games so all you are left to bring are your toiletries and food!

4.96 out of 5 average rating, 510 reviews

A refreshing seasonal pool displays sparkling blue water, surrounded by a spacious deck and lawns. A colorful striped pool float rests on the surface, while the historic Chapman House is visible in the background, framed by tall trees and sunlight filtering through.

Guesthouse in Rosemont

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

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Popular amenities for Cumberland rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 50 reviews

An inviting in-ground pool is surrounded by a stone patio, featuring several lounge chairs placed for relaxation. Lush greenery creates a serene backdrop, enhancing the space's natural appeal. A table with blue cushions sits nearby, providing a comfortable spot for outdoor dining.

Home in Newry

Mountain Hideaway - Outdoor pool, hot tub

MarvellaRating, 5 stars2 weeks ago

This place was perfectly set up for our stay. With a 2 bedroom mother in law suite down stairs and a secluded children’s quarter upstairs yet we all had access to each other area. The pool was amazing with beautiful light at night. The back yard was perfectly set up with an outdoor bar area. The loft was an added touch for sleeping space. I loved this place and wood definitely book it again

Home in Old Orchard Beach

A charming two-story home features a green-shingled exterior and a gabled roof. Large windows allow natural light to fill the interior. A white front door stands at the center, with a covered entryway. A fenced area is visible in the foreground, alongside designated parking spaces.

5 out of 5 average rating, 34 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

TrishRating, 5 stars2 days ago

we can't say enough about lovely our stay was at this beautiful house in OOB. the house is so clean and bright. its within walking distance to restaurants and stores. its right across from the heated pool. it really is such a gem!

5 out of 5 average rating, 51 reviews

An aerial view displays a saltwater pool, surrounded by lounge chairs and red umbrellas. A hot tub is located adjacent to the pool, and well-maintained landscaping is visible around the area, contributing to a spacious relaxation environment.

Home in Wells

2BR, Sea & Relax w/ Wells Reserve View

SamiraRating, 5 stars2 weeks ago

Jordanna’s place was beautiful and cozy! Perfect for a small family or girls trip up to 3 people. Place was spotless, lots to do in the area and will close proximity to Ogunquit and Kennebunkport. Would go back anytime!

5 out of 5 average rating, 9 reviews

An aerial view captures a spacious community area featuring a large swimming pool surrounded by lounge chairs. Lush greenery envelops the setting, enhancing the tranquil atmosphere. A small pond reflects the landscape, with walking paths guiding residents between the pool and neighboring homes.

Home in Arundel

Maritime Meadows – Charming Resort-Style Home!

JaneRating, 5 stars1 week ago

A beautiful home in a quiet neighborhood with everything you could need. Located a short distance from the beaches, towns, shopping and restaurants. We were here the last week of May when the crowds were not too bad. The weather was perfect—60’s and 70’s. The hosts are extremely responsive. Would definitely stay here again.

4.89 out of 5 average rating, 199 reviews

Home in Bartlett

Fireplaced Mountain King Suite w/Hot Tubs & Pools

PanidaRating, 5 stars2 weeks ago

Cute place. Everything we needed was available. Bed was comfortable as well as pull out couch. Enough towels and linen available. Very clean. Will stay again.

4.93 out of 5 average rating, 14 reviews

The exterior of Marty's Magic Haus is showcased with a wooden facade, surrounded by trees. A heated pool is visible on the patio, alongside a fire pit and seating area. Soft lighting creates an inviting atmosphere as the sun sets behind the house, reflecting off the windows.

Home in Bethel

NEW Marty's Magic Haus Ski, Bike & Hike Retreat

HaleyRating, 5 stars2 weeks ago

My friends and I felt right at home with our stay. Everything was clean and bright. Kitchen was stocked with everything needed. Loved using the hot tub and sauna. Unfortunately experienced a cold snap with Maine warming up for the summer and had lots of rain/overcast but it did not stop us from enjoying the house. With the time of year there was not a lot to do as we were early for the summer activities and this house is close for skiing. But I would definitely visit again at the right time of year! Also loved that the host was so responsive. It kept me comfortable during our stay.

4.92 out of 5 average rating, 13 reviews

A living area features a comfortable gray sofa and an accent chair with a small ottoman. A light-colored coffee table sits in the center. Two windows allow natural light to brighten the space, while a wall-mounted television adds to the room's functionality.

Home in Saco

Cottage ten minutes from beach

VincentRating, 5 stars2 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

An aerial view of a spacious backyard showcases a well-maintained heated pool surrounded by a patio area with seating. Lush greenery and trees frame the property, enhancing the outdoor space, while a shaded fire pit area and landscaped garden beds are visible.

Home in Stroudwater

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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Condo rentals with a pool

An open living area features a high wooden ceiling and light-colored walls. Two sofas and two leather chairs are arranged around a wooden coffee table. A Foosball table is visible in the background, along with a stairwell leading to the upper level.

4.98 out of 5 average rating, 130 reviews

Don’t miss out, book for Fall NOW!

CARISSARating, 5 stars3 months ago

This AirBnB was a perfect winter vacation escape. It had everything we needed for our two families. The kitchen was so well stocked and we were never without. Great set up. My 5 year old begged to live there forever! We can't wait to come back!

4.85 out of 5 average rating, 187 reviews

A large outdoor pool area is surrounded by lounge chairs in vibrant colors. The pool is complemented by neighboring buildings with multiple windows, providing a welcoming atmosphere. The concrete patio offers ample space for relaxation and sunbathing, with a barbecue area visible in the background.

Condo in Wells

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

SusanRating, 5 stars3 days 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

4.87 out of 5 average rating, 149 reviews

An indoor pool area is showcased with a spacious layout featuring large windows that allow natural light to fill the room. Several lounge chairs are arranged around the pool, providing a relaxing environment. The wooden ceiling adds warmth to the setting.

Condo in Bartlett

Spacious Condo-Attitash Ski-Storyland-Saco & More!

CristinRating, 5 stars2 days ago

Beautiful place to stay! Great amenities for the kids ! Will definitely go back ❤️

A tranquil pool area is surrounded by lush greenery. Comfortable lounge chairs are arranged on the pool deck, along with umbrellas for shade. The clear water reflects the tree canopy overhead, creating a serene atmosphere for relaxation.

4.89 out of 5 average rating, 142 reviews

Cozy 1 BR Resort Condo; Fireplace; Amazing views

MarcRating, 5 stars2 weeks ago

Great long weekend stay! Location perfect for trail/gravel biking, hiking, waterfall searching, and fly fishing! Perfect for 2…..great views to Doublehead and black mts. Accommodations were perfect. Kitchen stocked with essentials, large bathroom w separate jet tub…..and adequate hot water capacity to run it. Recommend highly.

A comfortable living area is presented with a dark leather sofa and two wooden lounge chairs. Soft lighting from lamps creates a warm ambiance. A coffee table stands at the center, and large sliding glass doors open to a view of the outdoor grounds.

4.89 out of 5 average rating, 264 reviews

Intimate Garden Style Condo with Mountain Views

MollyRating, 5 stars4 months ago

We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!

4.76 out of 5 average rating, 134 reviews

An outdoor heated pool is framed by lounge chairs, providing a space for relaxation. The pool reflects the two-story building behind, with large windows visible. Umbrellas offer shade on sunny days, and well-maintained grass surrounds the pool area.

Condo in Wells

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars2 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, 110 reviews

A well-maintained outdoor pool is enclosed by a chain-link fence, featuring a spacious deck with lounge chairs and umbrellas. Lush greenery surrounds the area, enhancing the tranquil environment. A pool cleaning net rests on the pool deck, indicating regular maintenance.

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!!!!

A seasonal outdoor pool is surrounded by landscaped gardens and lounge chairs, showcasing stunning mountain views. Lush greenery and colorful flowers frame the area, while a cozy seating area is visible in the distance beneath the clear blue sky.