Fitness-friendly holiday rentals in South Portland

Home in Old Orchard Beach

A three-story white house is situated in a spacious green yard, framed by tall trees. The exterior features multiple windows with black shutters and a welcoming front porch. A well-maintained pathway leads to the entrance, providing easy access from the driveway.

4.93 out of 5 average rating, 45 reviews

Entire Home 5 mins from Downtown

5 minute walk to downtown. 5 beds (2 queens, 2 doubles, one large daybed) 3 bedrooms, 2.5 baths, home theater with blackout shades, built in bar, large yard and driveway, detached home gym with full weight sets and built in audio, and laundry room. This 3 story home is a 5 minute walk to downtown and local beaches and has air conditioning and heat in every room. Comes with a beach cart filled with chairs, umbrella, towels and all you’ll need for your trip to the sandy shores of OOB. Pet Friendly

4.96 out of 5 average rating, 24 reviews

A spacious living area features a comfortable sectional couch arranged around a circular coffee table. Natural light fills the room through a large window dressed with light curtains. A decorative mirror and wall shelves add to the cozy decor, complemented by a patterned area rug.

Home in Wells

Captains Quarters

This rental is off the beaten path on a private road minutes from Wells' famed beaches, local attractions and dining hotspots. Enjoy easy access to outdoor recreational activities like kayaking, fishing, or simply strolling along the scenic riverbank. This spacious rental features three bedrooms, three bathrooms, and ample living space spread across 1536 square feet. The interior exudes a cozy ambiance, with tasteful furnishings, hardwood floors, and large windows allowing for natural light. Thi

4.77 out of 5 average rating, 26 reviews

The exterior of the lakefront home is showcased, featuring a mix of wooden and large glass-paneled walls. Surrounded by tall trees, the property includes a spacious deck and an inviting landscape with lush greenery and a path leading to the home.

Home in Naples

Pinecrest Lakefront, Private 1 Bedroom

Pricing is for 1 bed only. PLS DO NOT BOOK PEAK HOLIDAYS/WEEKENDS IN ADVANCE as we prefer to rent the larger listing 1st.You will have the entire house to yourself, no other guests.This waterfront retreat has everything to offer for a peaceful getaway, work remotely, relax or enjoy a gathering by the fire place, fire pit or beach. Only minutes from Naples, restaurants, stores and Sebago Lake State Park. Ski at Shawnee Peak(25min) or Sunday River(60 min.), Bridgton(15min) and North Conway(55min).

4.83 out of 5 average rating, 94 reviews

A modern kitchen features a central island with dark cabinetry and a built-in oven. A stylish hood vent hangs above the stove, with natural light flooding in through floor-to-ceiling windows that provide views of the outdoor space. The sleek countertops enhance the contemporary design.

Home in North Deering

Modern Coastal Escape • View Spa Hot Tub & Firepit

Welcome to your modern brand new custom built Coastal Escape! Relax in the private hot tub, gather at the fire pit, and cook like a pro in the fully equipped chef’s kitchen. Bedrooms: Four restful rooms with fresh linens and blackout shades. Outdoor perks: Spacious yard, grill, and Adirondack seating. SuperFast Fiber Optics Wi-Fi & Smart TVs Home Theater Washer/dryer Self-check-in Minutes to Portland’s Old Port, beaches, breweries, and hiking trails. Book now for year-round Maine adventure!

4.96 out of 5 average rating, 25 reviews

A waterfront scene showcases a charming two-story home surrounded by greenery. A spacious yard features seating areas arranged for gatherings. A wooden dock extends into the calm water, equipped with several black Adirondack chairs, inviting relaxation by the lake.

Home in Windham

Lakefront | Dock + Fire Pit Near Sebago & Portland

Experience the charm of Forest Lake just 28 mins from Sebago & Portland! Swim, kayak, paddleboard, or unwind on your private beach. Enjoy BBQs & bonfires in the spacious yard under the stars. Sleeps 7. Fully stocked home with 72" OLED TV, PS5, surround sound, and fast Wi-Fi. New heat pumps ensure comfort year-round. Whether you're after lakeside peace or easy access to southern Maine's best spots, your perfect escape awaits. Explore local trails, beaches, breweries, & classic Maine lake towns.

4.97 out of 5 average rating, 35 reviews

Home in Lyman

Family Friendly Kennebunk Pond Lakefront Retreat

Time of Wonder is a family-friendly vacation rental in coastal Maine, ideal for up to 6 guests. Nestled on Kennebunk Pond, this 3-bedroom, 2-bath home features a fire pit and hammock by the lake. Relax by your private dock while listening to loons and enjoying breathtaking sunsets. With two paddle boards available, lake fun is at your fingertips. Discover the charming towns of Kennebunk and Kennebunkport, along with their beautiful beaches. Plus, Kennebunk Pond is great for ice fishing too!!!

4.99 out of 5 average rating, 88 reviews

The living room features a comfortable couch paired with two chairs, illuminated by natural light through large windows. An exercise bike is positioned near the window, and a decorative area rug complements the space. A small table holds a candle, enhancing the cozy atmosphere.

Apartment in Falmouth

Sweet 2-story 1910 Bungalow near Portland, Beaches

This lovely, 2-story Sears-Roebuck 1910 bungalow with its own entrance has sea breezes in summer and fireside coziness in winter. Borrow bikes to explore nearby Town Landing beach, Audubon, and forest trails. Walk three blocks to a local bakery for coffee. The upstairs bedroom with a king bed looks out on white pines. Furnishings have been updated, but the original woodwork is untouched. Just 4 miles up the coast from Portland, it's a wonderful base for exploring Maine's towns and beaches.

Hotel room in Downtown Portland

A bright and airy sitting area is highlighted by large windows allowing natural light to fill the space. Two red armchairs and a gray chair are positioned around a wooden coffee table, complemented by a stylish floor lamp and a decorative vase with dried flowers.

4.89 out of 5 average rating, 163 reviews

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

5 out of 5 average rating, 13 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

We are out of the baby stage and ready to share our home while away. Our home is a great house for entertaining or just relaxing without feeling cramped. There are places for everyone, from the heated pool, the patio, or outdoor activities, to the many living/sitting rooms, gym or theater/game room. Located just minutes from the airport and minutes from downtown in the historic Stroudwater district or Portland. Sitting on nearly an acre on a small cul-de-sac of similar stately homes.

Holiday home in Old Orchard Beach

The charming rental features a white exterior with a wraparound porch accented by hanging flower baskets. The lush green lawn surrounds the property, and large windows offer glimpses of natural light within. The sloped roof adds character to this welcoming structure.

4.9 out of 5 average rating, 31 reviews

A Commanding View of Town of Old Orchard Beach

Distant Atlantic Ocean views from the lawn, deck, porch, or airy loft of this charming Old Orchard Beach rental. Perfectly located across from Walgreens for easy access to essentials. Both main bedrooms open directly outdoors to invite the fresh ocean breeze. Two additional converted sleeping areas, thoughtfully divided for privacy. Two showers and 4 parking spots. Explore “The Pier,” an iconic boardwalk, brimming with dining, and scenic charm. Your perfect coastal getaway awaits.

4.99 out of 5 average rating, 87 reviews

The image showcases a restored stone ranch home surrounded by greenery, a well-maintained lawn, and a driveway. Additionally, the home features an outdoor seating area lit by string lights, enhancing nighttime gatherings. Interior areas display stylish furniture and large windows, inviting ample natural light.

Home in Saco

Entire Home in Sunny Saco + Gym

This 3 bed 2 bath restored stone ranch in Saco awaits your next vacation to Coastal Maine. Here you will enjoy the best of both worlds, staying in a quiet community making memories in the private back yard while being just a short drive to Maine's most sought after beaches including OOB, Ferry Beach, and Hills Beach, to name a few. Also walkable to Saco's Historic downtown and just a short drive to thriving Biddeford. Kennebunkport and Portland are just a short 20 min drive too.

5 out of 5 average rating, 40 reviews

A two-story house with a light green exterior is framed by trees. A welcoming front porch features blue chairs, and a contrasting blue door enhances the entrance. A paved driveway leads to a garage with a white door, complementing the home's design.

Home in Scarborough

Captain Vacation House by beach, shopping, pets EV

Ahoy Mate! Welcome to Captain Vacation House, a nautical home inspired by a lifetime of a travel on the seven seas. Located in Scarborough, Maine accessible easily to the beaches, the Maine Mall shopping area, downtown Portland restaurants and activities and an easy jump onto all major highways. There is a sunny office that can be used as a fifth bedroom and a dedicated work space. With 4 Bedrooms, ten people can sleep comfortably. Cots and crib are available.

Popular amenities for South Portland fitness-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

5 out of 5 average rating, 34 reviews

An open living space is showcased, featuring a dining area with a light wooden table surrounded by white chairs. Comfortable seating arrangements include two armchairs and a couch, all illuminated by natural light from multiple windows. A well-equipped kitchen area is visible in the background.

Apartment in Bridgton

The Hideaway-Downtown Bridgton

A view from the balcony captures the vibrant amusement park with colorful rides, including a large Ferris wheel. The shoreline and ocean can be seen in the distance, providing a backdrop to the lively scene below, filled with shops and attractions.

4.86 out of 5 average rating, 14 reviews

Gorgeous Oceanview Condo

3.67 out of 5 average rating, 3 reviews

Camp Eilis Suite Old Orchard Beach

A bright kitchen opens to a dining area, characterized by large skylights allowing natural light to illuminate the space. Wooden cabinetry contrasts with stainless steel appliances. The dining table, surrounded by woven chairs, is positioned next to vertical blinds that frame the outdoor view.

Family Friendly condo w/ pool!

Apartment in Downtown Portland

5 out of 5 average rating, 15 reviews

One Bedroom Loft at Boyd Block

The image displays a modern kitchen featuring a dark countertop with light cabinetry, designed for a functional space. A patterned rug lies on the polished wooden floor, while natural light comes through the windows. A dining chair and seating area are visible in the background.

4.57 out of 5 average rating, 7 reviews

Seaside Condo Old Orchard Beach

A bright sunroom featuring large windows that allow natural light to fill the space. Two wooden chairs with green cushions are positioned next to a small wooden table. A light-colored couch adds additional seating, complemented by simple decor on the walls.

5 out of 5 average rating, 4 reviews

Two bedroom Apartment OOB

Apartment in Kennebunkport

The living area features a comfortable sofa adorned with decorative pillows, accompanied by a light-colored coffee table at its center. A wall-mounted clock and 'Welcome' sign enhance the cozy ambiance. Natural light filters through a window, offering a view of the greenery outside.

4.88 out of 5 average rating, 8 reviews

Family-Friendly Condo: Resort at Goose Rocks Beach

Fitness-friendly condo rentals

4.93 out of 5 average rating, 30 reviews

A compact dining area is presented with a white metal table and two chairs, surrounded by mint green and yellow walls. A decorative pendant light hangs above the table, and a wall-mounted planter adds a touch of color. A framed artwork is visible in the background.

Condo in Kennebunkport

Condo at the Resort at Goose Rocks

A vibrant view captures the amusement park, featuring a large Ferris wheel and colorful attractions. The beach stretches in the background, illuminated by a soft, pastel sunset. A lively crowd gathers below, enjoying the bustling atmosphere of the town square.

5 out of 5 average rating, 19 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

A wide, sandy beach stretches along the coastline, populated with beachgoers enjoying the sun. The blue ocean gently meets the shore, while grassy areas and structures are visible in the background, contributing to the lively seaside atmosphere.

4.9 out of 5 average rating, 10 reviews

Sky Deck Penthouse Condo, Walk to Beach and Pier

A cozy living area is presented with two stylish armchairs and a matching sofa, all decorated with patterned cushions. A round coffee table sits in the center, resting on a textured area rug. Large windows allow for natural light and views of the ocean.

4.83 out of 5 average rating, 59 reviews

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

A blue and white sign displays 'Saco Bay Condos' along with an anchor symbol, indicating the property’s name. The sign is mounted on a pole surrounded by power lines, while a nearby building features a shingled exterior. The atmosphere is relaxed and coastal.

4.95 out of 5 average rating, 22 reviews

Large 3 Bedroom/2 Bath Condo - Steps to the Beach!

An open living area features a dining table with black chairs, a comfortable brown leather sofa, and a wooden coffee table. A ceiling fan provides airflow, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

4.81 out of 5 average rating, 37 reviews

Maine, Beach front Condo! Vacation hotspot!

A well-maintained garden-style condo is displayed, featuring a private deck with patio furniture overlooking lush greenery. Several skylights are visible, enhancing natural light. The exterior showcases a combination of siding materials, and the entrance is framed by neatly trimmed hedges.

4.83 out of 5 average rating, 12 reviews

Family Vacation Home walking distance to Beach

A bright living area features a blue sofa adorned with striped cushions and a coffee table. Natural light fills the space through sliding glass doors that lead to the deck. A television is mounted on a wooden console, and stairs can be seen in the background.

4.5 out of 5 average rating, 8 reviews

Cape Cod style 2BR Waterview | Patio | Pool

Fitness-Friendly Holiday House

A charming brick home is surrounded by lush greenery, showcasing a welcoming front porch with white railings. The property features a scenic pathway leading up to the door, framed by trees and a manicured lawn.

Home in St. George

Historic Island Retreat

4.63 out of 5 average rating, 24 reviews

A modern kitchen with white cabinetry and stainless steel appliances is visible, featuring a gas stove and ample countertop space. A dining area with a round wooden table and rattan chairs is present, alongside a stylish mirrored console table that reflects natural light.

Home in Arundel

Beach Plum-Elegant Coastal Escape

A spacious deck is furnished with two striped lounge chairs and a dining area, featuring a table and several chairs under an umbrella. Large windows offer a view of the surrounding greenery, creating a relaxed outdoor atmosphere.

Home in Kennebunk

Beautiful Mousam River Retreat: Hot Tub & Kayaks!

The exterior of a three-story Victorian house is visible, showcasing a combination of white siding and brick accents. A set of stairs leads to a grand entrance with large windows, and the surrounding landscape features a manicured lawn and gravel pathway.

Home in Poland

Poland Spring Ricker House

4.96 out of 5 average rating, 23 reviews

A spiral wooden staircase ascends alongside a wall adorned with several guitars, adding artistic flair. Two comfortable armchairs are positioned near large windows, allowing natural light to brighten the space, while a potted plant enhances the inviting atmosphere.

Home in Kennebunkport

The Way Life Should Be Villa

The lakeside view displays a charming home surrounded by vibrant fall foliage, reflecting beautifully in the calm water. Comfortable seating is situated on the shore, offering a serene outdoor space. The light of the morning sun enhances the peaceful atmosphere of this lakeside retreat.

Home in Windham

SuperHost New Listing! Lakehouse Near Portland