Holiday rentals in Long Island

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Top-rated holiday rentals in Long Island

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Top guest favourite
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
4.95 out of 5 average rating, 656 reviews

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.

Superhost
A spacious dining area is highlighted by a wooden table surrounded by white chairs. A staircase with wooden railings leads to the upper level. Natural light fills the room through multiple windows, enhancing the warm wooden details of the walls and floor.
Loft in Portland
4.9 out of 5 average rating, 323 reviews

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

Top guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 187 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 429 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Guest favourite
A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.
Flat in Downtown Portland
4.96 out of 5 average rating, 286 reviews

Old Port Penthouse Suite - Amazing Harbor Views

2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Guest favourite
A bright bedroom features a queen bed with an ornate wooden headboard, flanked by two stylish wall lamps. Sliding glass doors provide access to the outdoors, while clerestory windows invite natural light. A cozy rug complements the wooden flooring, enhancing the spacious feel.
Flat in South Portland
4.93 out of 5 average rating, 168 reviews

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

Top guest favourite
A bright hallway leads into the living space, featuring light wood flooring and white walls. A dining area is seen to the left with a small table and chair, while decorative elements, including potted plants and books, add character to the space.
Flat in Peaks Island
4.98 out of 5 average rating, 197 reviews

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Guest favourite
The two elevated structures of the tree dwelling are connected by a rope bridge, surrounded by lush green trees. Natural materials are utilized in the design, which includes a balcony and multiple levels that create a unique, inviting silhouette against the forest backdrop.
Treehouse in Georgetown
4.98 out of 5 average rating, 446 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Guest favourite
A tranquil bedroom features a spacious bed covered with a light-colored bedspread. Soft light enters through a large window adorned with sheer curtains. A decorative mirror hangs on the wall, and a small chair is positioned near the closet, creating a calm and cozy environment.
Flat in East End
4.93 out of 5 average rating, 650 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Guest favourite
A welcoming living area features a light gray sectional sofa adorned with various textured pillows. A wooden coffee table sits on a neutral rug, accompanied by a dark, upholstered chair. Natural light filters through the two windows, complementing the space's relaxed ambiance.
Flat in West End
4.97 out of 5 average rating, 194 reviews

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Top guest favourite
A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.
Home in Harpswell
4.98 out of 5 average rating, 221 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

Superhost
A queen-size bed is dressed in crisp white linens, complemented by decorative pillows in rich hues. A textured throw blanket adds warmth across the foot of the bed. Soft natural light filters in through a nearby window, highlighting the cozy atmosphere.
Flat in Cumberland Mills
4.9 out of 5 average rating, 219 reviews

Cozy 2 BR Apt in Walking Distance to Restaurants

This is a private two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

Popular amenities for Long Island holiday rentals

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MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$407 SGD$407 SGD$650 SGD$420 SGD$585 SGD$587 SGD$650 SGD$553 SGD$498 SGD$520 SGD$650 SGD$406 SGD
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Quick stats about holiday rentals in Long Island

  • Total holiday rentals

    Explore 70 holiday rentals in Long Island

  • Nightly prices starting at

    Long Island holiday rentals start at $117 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Long Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym and BBQ grill across Long Island rentals

  • 4.9 Average rating

    Long Island stays are highly rated by guests – averaging 4.9 out of 5!

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