
Vacation rentals in Long Island
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Top-rated vacation rentals in Long Island
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Private Sauna+Near Beach+FirePit+Forest View+Pond
Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Backup Automatic Generator * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Cozy SoPo Condo
Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

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.

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.

1BR cozy, luxurious getaway @ Krista's Guesthouse
Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

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!).

Beautiful Kettle Cove Apt Steps to Beaches
Enjoy some of the Portland area’s finest destinations year-round. This sunny, 1 BR ground floor apt in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests and ponds are a stroll away while downtown Portland is an easy 15-minute drive. The apartment is a great base to explore Southern Maine from and an equally great location to chill out and soak in coastal Maine’s restorative water and air.

Cape Elizabeth Garden Apt+Beach+Close to Portland!
Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

Birch Ledge Guesthouse--Four Season Maine Getaway
Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

The Roost - lovely one bedroom efficiency unit
Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.
Popular amenities for Long Island vacation rentals
Other great vacation rentals in Long Island

Waterfront Cottage in Freeport

Casco-Vista, Island Cottage

Modern Cottage with Peeks of Ocean Views

The Maine Frame: Modern A-Frame Cabin | Freeport

Cheerful, Sunny, 3 Bedroom Island Home

Seacret Seaside Cottage, charming 3 bedroom

Entire Ideally Located Cape Elizabeth Home

"Periwinkle" ~ a Charming Oceanfront Cottage
When is the best time to visit Long Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $428 CAD | $428 CAD | $684 CAD | $442 CAD | $615 CAD | $617 CAD | $684 CAD | $593 CAD | $614 CAD | $547 CAD | $684 CAD | $427 CAD |
| 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 1,070 vacation rentals in Peaks Island, and over 90 vacation rentals in Cliff 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 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.
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 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 $123Â CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 of Long Island vacation 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!
Destinations to explore
- Plainview Vacation rentals
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- Family-friendly rentals Long Island
- Rentals with beach access Long Island
- Rentals with outdoor seating Long Island
- Rentals with a fireplace Long Island
- House rentals Long Island
- Waterfront rentals Long Island
- Rentals with a washer and dryer Long Island
- Pet-friendly rentals Long Island
- Rentals with a patio Long Island
- Cottage 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
- King Pine Ski Area
- Dunegrass Golf Club
- Willard Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Short Sands Beach
- Gooch's Beach
- Parsons Beach
- Cliff House Beach
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Ferry Beach
- Laudholm Beach




