Holiday rentals with a pool in Kennebunk

5.0 out of 5 average rating, 105 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Welcome to your Ogunquit Oasis, a luxurious 5-bedroom beach house located on the edge of Ogunquit Village. Walk to the beach, restaurants, Perkins Cove, Marginal Way & everything in Ogunquit! The house features a heated pool that reaches 104 degrees, ideal for all seasons. Built in 2014, the house includes central air, three Ultra HD TVs, and wireless speakers. The dining table seats 10, with an outdoor living room, grill, & gas firepit. Each spacious bedroom offers plush bedding & ceiling fans.

Apartment in Kennebunkport

A charming two-story white house features a covered porch with railing and a central double-door entry. Lush greenery and colorful flower beds surround the property, enhancing the welcoming appearance. Large windows invite natural light, and the roof is adorned with shingles.

Luxury Coastal Retreat | Mins from Dock Square

Minutes to Dock Square, beaches, and local restaurants. Escape to Cape Porpoise, Kennebunkport. Sea Glass is a luxury 1BR condo with ocean views, fire pit, designer interiors, a seasonal pool & LOCATION. Relax by the fire pit, walk to shops, explore the beaches, and enjoy a coastal retreat year-round. Perfect for getaways, remote work, or a classic Maine coast vacation. Experience Maine’s winter charm, spring beauty, beautiful summer and fall foliage at SeaGlass. Permit Number: STR-0008560

4.99 out of 5 average rating, 70 reviews

A grassy area features seating made up of Adirondack chairs and a patio table set, facing a row of cottages with large windows. The clear sky above is dotted with clouds, complementing the peaceful surroundings.

4.93 out of 5 average rating, 213 reviews

Wells Maine Home with a View

Our Contemporary Cottages, at Seagull, gracefully sits on a grassy 11 acre bluff with panoramic views of the Rachel Carson Refuge and the Atlantic Ocean. This tastefully decorated cottages offer air conditioning, heat, ceiling fans, fully equipped kitchen with dishwasher, gas grill, cable TV, skylights, and a large screened in porch with sliding glass doors opening into the livingroom and master bedroom. Cottage has a great pool/hot tub. WIth ocean view and comfortably accommodates six guests.

4.96 out of 5 average rating, 179 reviews

A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You 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 shops and restaurants. 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, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

4.9 out of 5 average rating, 120 reviews

Apartment in Wells

Starfish Condo Wells Beach

Enjoy the amazing sunrise as well as marsh and ocean views from this spacious just renovated one and a half bedroom condo with queen bed and queen Murphy bed. Fully equipped kitchen with granite counter tops and stainless steel appliances. Updated full bath with tub. Located within walking distance to many local area restaurants. After a fun filled day on the beach relax by the salt water pool or in the hot tub. Shared gas grill, picnic area, playground and basketball hoop. Parking for one car

5.0 out of 5 average rating, 14 reviews

Home in Arundel

Designers Dream Home with Pool!

Discover this brand-new, beautifully appointed 2-bedroom home nestled within a secure, private community surrounded by 200 acres of preserved natural beauty. Enjoy full access to outdoor heated pools, a clubhouse featuring a game room (with ping pong, foosball, shuffleboard, and a poker room), and a fully equipped fitness center to keep you on routine. Mingle with fellow guests at the clubhouse or relax in your peaceful, private backyard, and enjoy the perfect balance of activity and serenity.

4.97 out of 5 average rating, 109 reviews

The living area features a plush gray sofa and an armchair beside a large area rug. Natural light filters through a skylight, illuminating the space. A coffee table sits at the center, accompanied by two lamps and a faux fireplace, creating a cozy ambiance.

Apartment in Ogunquit

Newly designed one-bedroom condo- heart of OGT

The newly furnished condo is located right in the center of everything that beautiful Ogunquit has to offer. Just a five minute walk to the beach and even closer to Ogunquit's landmark restaurants and bars, this is the most desirable location to stay in Ogunquit. Enjoy free on-site parking, a BBQ and on-site pool access. I am an airbnb super-host and an artist, whose first dance gig was at the Ogunquit Playhouse just up the street. I appreciate your rental as a way to support local artists.

4.98 out of 5 average rating, 59 reviews

A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.

Home in Kennebunkport

Lovely Beach house in GRB - Heated pool!

Goose Rocks Beach Retreat | Heated Saltwater Pool & Ocean Views Just steps from beautiful Goose Rocks Beach, this classic coastal retreat offers the perfect setting for a memorable Maine getaway. Designed for families and groups, the home features a bright open-concept living space, a large deck with ocean views, and a heated saltwater pool (seasonal, typically May-Oct weather permitting). Enjoy easy beach access, plenty of room to gather, and all the comforts needed for a relaxing stay!

Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

5.0 out of 5 average rating, 145 reviews

4.96 out of 5 average rating, 133 reviews

A modern kitchen is showcased with white cabinetry and granite countertops. Stainless steel appliances include a refrigerator, microwave, and dishwasher. Kitchenware is neatly arranged, enhancing the functional space. A light blue wall adds a calm touch, while a throw pillow with 'BEACH.' text provides a decorative element.

Apartment in Wells

Steps to Wells Beach + Pool | Coastal Retreat

Stay steps from Wells Beach in this renovated coastal condo with an onsite pool, clean modern interior, and prime walkable location off Atlantic Avenue. Walk to the sand in minutes, enjoy the ocean air from your patio, relax by the pool, and explore nearby shops, dining, playground, and arcade. Perfect for couples, small families, or a small group, this one bedroom condo makes an easy Southern Maine escape for visiting Wells, Ogunquit, Kennebunkport and the classic New England coast!

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.

4.95 out of 5 average rating, 180 reviews

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.

4.98 out of 5 average rating, 200 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Popular amenities for Kennebunk rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Old Orchard Beach

A serene community pool is surrounded by a spacious deck with lounge chairs for relaxation. Tall trees in the background provide a natural setting, while neighboring homes are visible, enhancing the sense of community.

Faith Lane with community pool

4.96 out of 5 average rating, 123 reviews

4.93 out of 5 average rating, 287 reviews

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

Sanctum by the Lake

5.0 out of 5 average rating, 21 reviews

An aerial view captures a community pool framed by lush greenery. The pool features a sandy area with scattered lounge chairs, while vibrant trees surround the space, enhancing the natural setting. Nearby buildings and pathways suggest a welcoming atmosphere for guests.

Home in Arundel

Maritime Meadows – Charming Resort-Style Home!

4.83 out of 5 average rating, 12 reviews

Home in Kennebunkport

Peaceful Cape Porpoise Retreat (House Only)

5.0 out of 5 average rating, 36 reviews

A single-story home features a welcoming façade with a mix of stone and wooden elements. A spacious stone patio surrounds a circular fire pit, inviting outdoor gatherings. Lush greenery encircles the property, complementing the home’s charming exterior and large windows that provide ample natural light.

Home in Biddeford

The Hurkle Durkle House

4.96 out of 5 average rating, 69 reviews

A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.

Home in Kittery

Fantastic Kittery Home with Pool

4.95 out of 5 average rating, 74 reviews

Home in Standish

Unique Church Stay • Sebago Lake • Pool • Fire Pit

Superhost

An expansive backyard features a heated inground pool, surrounded by a spacious concrete patio. The white two-story house provides a backdrop with large windows and a sunroom that overlooks the pool area. Comfortable seating areas are visible, enhancing the outdoor space.

Home in Wells

Stunning Beach House with an in-ground pool!

4.67 out of 5 average rating, 24 reviews

Apartment rentals with a pool

A warm living and dining area features a wooden dining table surrounded by five chairs, a stone fireplace, and a comfortable seating arrangement with a brown sofa. Large windows allow ample natural light, complemented by a rustic chandelier overhead.

4.84 out of 5 average rating, 122 reviews

Elevate Your Adventure: Book Slope side Now!

4.93 out of 5 average rating, 128 reviews

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

A cozy living area is furnished with a light green sectional sofa and a comfortable armchair. Natural light enters through sliding glass doors, which lead to a deck. A decorative area rug is laid over hardwood flooring, and a brick fireplace adds warmth to the space.

4.98 out of 5 average rating, 199 reviews

3BR, 2BA condo in No. Conway, Close to everything!

A living room showcases a cozy seating area with two black sofas facing a television. A coffee table is centrally placed, adorned with a candle and a snack. A brick fireplace adds warmth, while natural light filters through the dual windows, dressed with light curtains.

4.96 out of 5 average rating, 134 reviews

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

5.0 out of 5 average rating, 112 reviews

Apartment in Intervale

Spectacular Mountain Views, at Eagle Ridge !

Apartment in Hampton Beach

A bottle of 406 Co. Cellars wine rests on a wooden table beside two clear wine glasses. A decorative blue sign reading 'Hampton Beach' adds a touch of local charm to the setting. Soft lighting creates a warm ambiance.

406 Co. Seascape

4.97 out of 5 average rating, 102 reviews

4.97 out of 5 average rating, 124 reviews

The Gibson Building 3BR

A serene view of a calm river surrounded by lush greenery. Gentle slopes lead to sandy banks, while trees provide a natural border on either side. The water reflects the blue sky above, creating a peaceful ambiance ideal for outdoor relaxation.

4.91 out of 5 average rating, 149 reviews

Cozy Family Retreat with Saco River Access

Other holiday rentals with a pool

4.98 out of 5 average rating, 55 reviews

Flat in Kennebunkport

Maine Coastal Village Getaway

5.0 out of 5 average rating, 94 reviews

Paradise Found Minutes from Ogunquit | Heated Pool

4.95 out of 5 average rating, 75 reviews

Ocean Beach Cottage Wells, ME

A charming cottage exterior is showcased with a bright blue front door. The welcoming porch features white rocking chairs and potted plants. Large windows with dark shutters allow natural light into the home, enhancing the inviting presence of the property.

4.98 out of 5 average rating, 91 reviews

Super cute one bedroom with hot tub and pool.

4.93 out of 5 average rating, 56 reviews

Flat in Wells

Walk to Wells Beach | Pool | Hot Tub

4.95 out of 5 average rating, 20 reviews

A bright studio space features light blue walls and a combination of yellow and navy decor. A spacious bed with a navy bedspread is positioned next to a cozy gray couch. Natural light floods the room from large windows and a door providing access to the outdoors.

Flat in Wells

Studio Condo, Deck, Pool, Hot Tub, Playground

4.88 out of 5 average rating, 34 reviews

A light-filled living room features a neutral color palette with wood floors. A large television is mounted on the wall above a contemporary media console, adorned with books and decorative items. A surfboard is displayed on the wall, while a cozy sofa invites relaxation.

Home in Wells

Remedy Retreathouse