
Holiday rentals in Long Island
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Top-rated holiday rentals in Long Island
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

LUX Designer Private Waterfront Hot Tub - Secluded
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

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!

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Hope Cottage: Peaceful Island Getaway
*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. Great biking, hiking, swimming, and kayaking.

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.

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.

Oceanfront w/ Stunning views and Private Deck☀️🏖
Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

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!

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.

Private Guesthouse in the Woods
Charming Yarmouth, Maine! This picturesque town offers the perfect blend of small-town charm and modern conveniences. Explore beautiful coastal landscapes, indulge in outdoor activities, and savor the vibrant local culture. This gem boasts spacious interiors, updated kitchen, and a serene backyard. Enjoy proximity to parks, shops, and dining. Don't miss the opportunity to enjoy relaxing in our Yarmouth home!
Popular amenities for Long Island holiday rentals
Other great holiday rentals in Long Island

Casco-Vista, Island Cottage

Peaks Island Casco Bay View Condo w/ Beach Access

Spruce Ledge Boathouse

Chickadee A-Frame

"The Cottage" on Peaks Island

Classic Peaks Island Cottage - 5 min walk to Ferry

Secluded Coastal Home & Cottage 3 Minutes to Beach

Ocean Views Near Beach w/ AC • Dog Friendly
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 1,060 vacation rentals in Peaks Island, over 90 vacation rentals in Cliff Island, and over 1,060 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 wifi, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Long Island

Total holiday rentals
Explore 60 holiday rentals in Long Island

Nightly prices starting at
Long Island holiday rentals start at £83 per night before taxes and fees

Verified guest reviews
Over 2,100 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

4.8 Average rating
Long Island stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with outdoor seating Long Island
- Waterfront rentals Long Island
- House rentals Long Island
- Rentals with beach access Long Island
- Family-friendly rentals Long Island
- Rentals with a patio Long Island
- Pet-friendly rentals Long Island
- Rentals with a fireplace Long Island
- Cottage rentals Long Island
- Rentals with a washing machine and dryer Long Island
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- East End Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Footbridge Beach
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park
- Palace Playland
- Hills Beach




