Long Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Long Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Scarborough

4.85 out of 5 average rating, 279 reviews

Charming beach cottage

Pine Point is a beautiful sleepy village surrounded on three sides by water: peaceful salt marsh, river to the sea, and ocean, with an 8 mile long white sand beach, extensive sand bars at low tide (great for sand dollars!). It is the perfect spot for an unforgettable family vacation. The beach here is considered by many to be the best walking and activity beach in Maine, as well as spectacularly beautiful. Come experience an idyllic week at the beach in Pine Point. This beach is perfect for many reasons: great swimming, windsurfing, beach combing, extensive sandbars, fishing off the jetty. The cottage is located in a quaint and quiet neighborhood, just steps from the path to the beach. Spend your days reading and sunbathing, and fall asleep at night to the sounds of the ocean just outside your window. The house has an open layout downstairs with a light breezy feel, and cozy upstairs sleeping quarters. Beautiful back yard and great deck in the shade, front porch with hammock for afternoon snoozes, and all the amenities of home. 20 minutes from the great little city of Portland for added excitement.

Apr 22 – 29

R2,124 ZAR per night
Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Enjoy the historical charm of one of Gorham's oldest homes. Come stay in a lovely private second floor, one bedroom apartment with private entry. Just walking distance from restaurants, the grocery store, laundromat, college campus and local trails. It offers private off-street parking for one car and it is located in the heart of Gorham village, a safe and family oriented community. Private bedroom with queen size bed and a full size futon provided. No backyard access. Full Kitchen. Full bath.

Apr 17 – 24

R2,155 ZAR per night
Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 278 reviews

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 to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. 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.

Apr 25 – 30

R3,051 ZAR per night

Popular amenities for Long Island vacation rentals

Stay near Long Island's top sights

Peaks Island176 locals recommend
Battery Steele4 locals recommend
Diamond's Edge Restaurant and Marina13 locals recommend
Fifth Maine Regiment Museum6 locals recommend
Crown Jewel7 locals recommend
Byers & Sons Long Island Bakehouse3 locals recommend

Other great vacation rentals in Long Island

Superhost

Apartment in Scarborough

4.85 out of 5 average rating, 433 reviews

Tiny Pine Point Beach Pad - comfy, cozy surf shed

Apr 13 – 20

R2,011 ZAR per night
Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 214 reviews

Cottage on Black Brook Preserve

May 30 – Jun 6

R2,396 ZAR per night
Guest favorite

Cottage in Scarborough

4.97 out of 5 average rating, 161 reviews

Bright, clean, private cottage near Higgins Beach!

Feb 22 – Mar 1

R2,983 ZAR per night
Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 114 reviews

Solar Suite surrounded by Nature

Nov 23 – 30

R2,311 ZAR per night
Guest favorite

Guest suite in Cumberland

4.92 out of 5 average rating, 108 reviews

Springer Park! adorable guesthouse very stylish!

Jan 22 – 29

R2,825 ZAR per night
Guest favorite

Loft in South Portland

5.0 out of 5 average rating, 105 reviews

Serene studio apartment, close to everything.

Apr 21 – 26

R2,612 ZAR per night
Superhost

Apartment in Portland

4.82 out of 5 average rating, 347 reviews

Spacious and Comfortable Private Apartment

Mar 9 – 16

R1,238 ZAR per night
Guest favorite

Apartment in Portland

4.85 out of 5 average rating, 437 reviews

Cozy, Private Apartment

Nov 11 – 18

R2,254 ZAR per night
Guest favorite

Guest suite in Scarborough

4.98 out of 5 average rating, 138 reviews

Beautiful, private apartment!! Great location!

Nov 4 – 11

R2,489 ZAR per night
Guest favorite

Apartment in Portland

4.9 out of 5 average rating, 342 reviews

Hip & Cozy, high end Modern Design

Dec 9 – 16

R2,553 ZAR per night
Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 428 reviews

Harpswell Studio on Waterview Property! Lobster!

Nov 5 – 12

R2,597 ZAR per night
Guest favorite

Guest suite in Windham

4.93 out of 5 average rating, 149 reviews

Millers Private Studio on Highland Lake

Sep 16 – 23

R2,180 ZAR per night

Other great vacation rentals in Long Island

Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 106 reviews

Tiny Island Cottage Hideaway, close to everything

Feb 5 – 12

R4,542 ZAR per night
Guest favorite

Condo in Portland

4.96 out of 5 average rating, 159 reviews

"Cornelia" Penthouse Waterfront Suite

Jan 12 – 19

R7,948 ZAR per night
Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 469 reviews

Cozy Cottage-Near Harbor & Park

Sep 30 – Oct 7

R3,349 ZAR per night
Guest favorite

Home in Portland

4.95 out of 5 average rating, 291 reviews

Explore Portland from a 18th-Century Victorian

Mar 22 – 29

R3,247 ZAR per night
Superhost

Apartment in Portland

4.88 out of 5 average rating, 374 reviews

Modern East End studio, perfect Portland home base

Nov 27 – Dec 4

R2,276 ZAR per night
Guest favorite

Guest suite in Westbrook

4.93 out of 5 average rating, 208 reviews

Awesome open space in Westbrook near Portland, ME!

Jun 17 – 24

R2,057 ZAR per night
Guest favorite

Apartment in Portland

4.82 out of 5 average rating, 426 reviews

Walk-able Portland Studio

Dec 11 – 18

R2,518 ZAR per night
Guest favorite

Apartment in Falmouth

5.0 out of 5 average rating, 36 reviews

Sweet 2-story 1910 Bungalow near Portland, Beaches

Dec 6 – 13

R2,354 ZAR per night
Guest favorite

Apartment in Portland

5.0 out of 5 average rating, 72 reviews

Peaks Master Bedroom Suite

Nov 19 – 26

R3,584 ZAR per night
Guest favorite

Guesthouse in Freeport

5.0 out of 5 average rating, 23 reviews

Mast Landing Cottage

Feb 18 – 25

R2,445 ZAR per night
Guest favorite

Apartment in Yarmouth

4.94 out of 5 average rating, 50 reviews

Flower Farm Studio Apartment

Feb 1 – 8

R2,009 ZAR per night
Guest favorite

Apartment in Yarmouth

4.96 out of 5 average rating, 92 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Apr 17 – 24

R2,751 ZAR per night

Quick stats about vacation rentals in Long Island

Total rentals

60 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

2K reviews

Nightly prices starting at

R1,515 ZAR before taxes and fees

Frequently Asked Questions

  • 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 cottage rentals in Long Island?

    Experience the best of Long Island with our cottage rentals, starting at about $80 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 20 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Long Island