
Holiday rentals in Long Island
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Top-rated holiday rentals in Long Island
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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.

Romantic A-Frame cabin in the woods
Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Amazing Bay View Home with Hot Tub
This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

"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 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Yurt on Chebeague Island
Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Luxury Year-round Treehouse with private hot tub
Skyframe is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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.

Pristine Waterfront Studio Apt. Retreat
Studio apt. on the water where Casco Bay meets the Presumpscot River. Downtown Portland 2 minutes away. Perfect to... *Relax & enjoy the sunset & water views from decks *Head into Portland-Bon Appetite 2018 Restaurant City of the Year & "The Best Lobster Roles in Maine" *CNN named Portland as "one of the best towns to visit in 2024" *Drive up the coast, explore the beautiful beaches, lighthouses, quaint towns *Adventure inland for amazing hikes & mountainous views *Awesome music scene!

Higgins Beach *New* Beach Home & Private Offices
Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Beautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests so if you'd like to book please introduce yourselves and let us know who is coming. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Garrison Cove Studio
Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.
Popular amenities for Long Island holiday rentals
Other great holiday rentals in Long Island

Yurtvana

Amazing location! Cheerful home near LL Bean

Maine Oceanfront Retreat

Nordic House | Glamping Cabin w Private Hot Tub

2-Bedroom Condo Close to Downtown

Modern Forest Cabin w/ Private Hot Tub & Fire Pit

Charming Cottage house, 2 bedrooms & Jacuzzi tub

Old Port Loft - 301
Frequently Asked Questions
Where should I stay in Long Island?
Make yourself at home in Long Island by choosing from our most frequently booked neighborhoods. We have over 1,040 vacation rentals in Peaks Island, over 90 vacation rentals in Cliff Island, and over 1,040 vacation rentals in Saint George.
Are there pet-friendly vacation rentals in Long Island?
Four-legged friends are welcome in Long Island. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Long Island?
Yes! Work meets play with ease at over 20 vacation rentals in Long Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Long Island?
Long Island has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cottage rentals in Long Island?
Experience the best of Long Island with our cottage rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Long Island have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Long Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Long Island have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Long Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Long Island?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 €95 per night before taxes and fees

Verified guest reviews
Over 2,170 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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- Rentals with outdoor seating Long Island
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- Waterfront rentals Long Island
- Rentals with beach access Long Island
- Cottage rentals Long Island
- Pet-friendly rentals Long Island
- Rentals with a fireplace Long Island
- Family-friendly rentals Long Island
- Rentals with a patio Long Island
- House rentals Long Island
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Scarborough Beach
- Willard Beach
- Short Sands Beach
- Pemaquid Beach
- Popham Beach State Park
- East End Beach
- Pemaquid Point Lighthouse
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Footbridge Beach
- Wolfe's Neck Woods State Park
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Pleasant Mountain Ski Area
- Hills Beach
- Funtown Splashtown USA
- Palace Playland





