Long Island vacation rentals

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Top-rated vacation rentals in Long Island

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

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Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.

Dec 5 – 12

R2,346 ZAR per night

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 109 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Sep 28 – Oct 5

R2,222 ZAR per night

Guest favorite

Loft in Freeport

4.97 out of 5 average rating, 194 reviews

Cozy & Private Studio Apartment (Pet Friendly!)

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Cable, Netflix, Disney Plus, Hulu and Amazon). Very comfortable queen size bed with floor space for kids if desired. Fantastically located just over a mile from beautiful Winslow Park's walking trails and beach, four miles south of downtown Freeport's shopping and 15 miles north of the popular city of Portland. Housebroken and well behaved pets welcome to join their humans!

Apr 18 – 25

R2,349 ZAR per night

Guest favorite

Guest suite in Scarborough

4.98 out of 5 average rating, 138 reviews

Beautiful, private apartment!! Great location!

Beautiful 750 square foot in-law apartment with private entrance. Full bedroom, bathroom, kitchen (including dishwasher), washer/dryer, and garage parking. Free wi-fi, cable, and Netflix included! All essentials included in addition to beach towels, chairs, table & cooler for the beach. Private patio includes a grill for use as well (weather permitting). Great location - 10 minutes to downtown Portland, 15 minutes to multiple beaches, 5 minutes to mall & restaurants.

Nov 27 – Dec 4

R2,193 ZAR per night

Guest favorite

Apartment in Portland

4.93 out of 5 average rating, 551 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Nov 29 – Dec 6

R1,809 ZAR per night

Guest favorite

Guest suite in South Portland

5.0 out of 5 average rating, 168 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

Jan 31 – Feb 7

R2,027 ZAR per night

Guest favorite

Guest suite in Portland

4.91 out of 5 average rating, 195 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Feb 20 – 27

R1,917 ZAR per night

Guest favorite

Guesthouse in Cape Elizabeth

4.98 out of 5 average rating, 138 reviews

Newly built private guest suite off Shore Road

Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.

Mar 30 – Apr 6

R3,115 ZAR per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 215 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Jun 28 – Jul 5

R2,386 ZAR per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 194 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

R1,313 ZAR per night

Guest favorite

Apartment in Portland

4.96 out of 5 average rating, 151 reviews

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

Dec 10 – 17

R2,509 ZAR per night

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 331 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

Jan 18 – 25

R1,248 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Long Island vacation rentals

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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

Guest favorite

Condo in Portland

4.85 out of 5 average rating, 203 reviews

Old Port on foot-additional parking option avail

Dec 13 – 20

R2,009 ZAR per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

Nov 14 – 21

R2,171 ZAR per night

Guest favorite

Farm stay in Gray

4.94 out of 5 average rating, 246 reviews

Great Goat Get-away in Southern Maine!

Jan 5 – 12

R2,703 ZAR per night

Guest favorite

Guest suite in Freeport

4.97 out of 5 average rating, 116 reviews

Solar Suite surrounded by Nature

Dec 2 – 9

R2,301 ZAR per night

Superhost

Guest suite in Westbrook

4.84 out of 5 average rating, 266 reviews

Comfy one bedroom suite

Jul 10 – 17

R2,210 ZAR per night

Guest favorite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Sep 17 – 24

R2,829 ZAR per night

Guest favorite

Apartment in Portland

4.94 out of 5 average rating, 372 reviews

Charming West End Victorian

Nov 26 – Dec 3

R2,277 ZAR per night

Guest favorite

Cottage in Portland

4.9 out of 5 average rating, 488 reviews

Cozy & Quiet Modern Cottage

Jul 23 – 30

R3,288 ZAR per night

Show all

Other great vacation rentals in Long Island

Guest favorite

Apartment in Freeport

4.91 out of 5 average rating, 195 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

Mar 9 – 16

R2,093 ZAR per night

Guest favorite

Cottage in Pownal

4.99 out of 5 average rating, 322 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Feb 16 – 23

R5,183 ZAR per night

Guest favorite

Guesthouse in Georgetown

4.9 out of 5 average rating, 136 reviews

Island Alchemy Cottage

Aug 16 – 23

R2,349 ZAR per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 429 reviews

Harpswell Studio on Waterview Property! Lobster!

Aug 13 – 20

R2,933 ZAR per night

Guest favorite

Home in Yarmouth

4.92 out of 5 average rating, 484 reviews

Beautiful Coastal Maine Getaway

Nov 15 – 22

R7,204 ZAR per night

Superhost

Cottage in Long Island

4.79 out of 5 average rating, 42 reviews

Picturesque Maine water view Long Island

May 30 – Jun 6

R9,413 ZAR per night

Guest favorite

Apartment in Falmouth

5.0 out of 5 average rating, 38 reviews

Sweet 2-story 1910 Bungalow near Portland, Beaches

Jan 17 – 24

R2,344 ZAR per night

Guest favorite

Cottage in Portland

5.0 out of 5 average rating, 8 reviews

Captain's Quarters on Peaks Island

Dec 12 – 19

R5,829 ZAR per night

Show all

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	R1,508 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 cottage rentals in Long Island have wifi?
Absolutely! We offer over 20 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.

Long Island vacation rentals

Top-rated vacation rentals in Long Island

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Long Island vacation rentals

Stay near Long Island's top sights

Other great vacation rentals in Long Island

Condo in Portland

Guest suite in Windham

Farm stay in Gray

Guest suite in Freeport

Guest suite in Westbrook

Tiny home in Portland

Apartment in Portland

Cottage in Portland

Other great vacation rentals in Long Island

Apartment in Freeport

Cottage in Pownal

Guesthouse in Georgetown

Guesthouse in Harpswell

Home in Yarmouth

Cottage in Long Island

Apartment in Falmouth

Cottage in Portland

Quick stats about vacation rentals in Long Island

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Long Island?

Are there pet-friendly vacation rentals in Long Island?

How much does it cost to stay in cottage rentals in Long Island?

Are there family-friendly cottage rentals in Long Island?

Do cottage rentals in Long Island have wifi?

Do house rentals in Long Island have a bbq area?

Destinations to explore