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

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!

Winter Dates: Cozy and 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.

Falmouth Waterfront Carriage House Apt
Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

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.

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.

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!).

Cozy tiny home | Fireplace-9 mi to Portland!
This unique cottage has a style all its own. Discover modern comfort in our brand-new suburban tiny home located in The Downs in Scarborough, ME! This stylish space offers all-new amenities and a cozy atmosphere. Ideal for solo travelers or couples, but can accommodate up to four guests. Enjoy a private escape while being ~9 miles from Portland and ~6 miles from the beach. Experience efficient living without compromising on luxury. Book now for a fresh, contemporary getaway!

Waterfront Two Master Suite Penthouse with Rooftop
2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

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.
Popular amenities for Long Island vacation rentals
Other great vacation rentals in Long Island

Rising Tide Times - quintessential Maine cottage

Luxury Year-round Treehouse with private hot tub

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Waterfront Private Apartment only 5 min to LLBean!

Crescent Beach Gardens

Private Sauna+Beach/Hiking Close+FirePit+S'mores

Romantic New England Historic Schoolhouse c1866

Stunning Ocean Views From This Peaks Island Home
When is the best time to visit Long Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$65,470 GYD | G$65,470 GYD | G$104,584 GYD | G$67,561 GYD | G$94,126 GYD | G$94,335 GYD | G$104,584 GYD | G$90,779 GYD | G$93,916 GYD | G$83,667 GYD | G$104,584 GYD | G$65,260 GYD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
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 90 vacation rentals in Cliff Island, and over 1,070 vacation rentals in Peaks Island.
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 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.
How much does it cost to stay in house rentals in Long Island?
Experience the best of Long Island with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly cottage rentals in Long Island?
Long Island has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Long Island have wifi?
Absolutely! We offer over 30 house rentals with wifi in Long Island. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Long Island have a bbq area?
Absolutely! We offer over 10 cottage 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 Cottage Rentals in Long Island?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Long Island

Total vacation rentals
Explore 70 vacation rentals in Long Island

Nightly prices starting at
Long Island vacation rentals start at G$18,825 GYD per night before taxes and fees

Verified guest reviews
Over 2,140 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Long Island vacation rentals include wi-fi 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
- Family-friendly rentals Long Island
- Rentals with a fireplace Long Island
- Waterfront rentals Long Island
- Rentals with a washer and dryer Long Island
- Rentals with beach access Long Island
- Cottage rentals Long Island
- Pet-friendly rentals Long Island
- Rentals with a patio Long Island
- House rentals Long Island
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Sands Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Dunegrass Golf Club
- King Pine Ski Area
- Willard Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Wolfe's Neck Woods State Park
- Short Sands Beach
- Parsons Beach
- Gooch's Beach
- Crescent Beach State Park
- Ferry Beach
- Laudholm Beach




