Top 50 Long Island Vacation Rentals

Houses (574)
Cottages (295)
Condos (128)
Golf rental (713)
Ocean view (440)
Beachfront (353)

Explore a selection of Long Island vacation rentals

Cozy Cottage Near Fowler's Beach
Guests5
Bedrooms2
Bathroom1
Wonderful 5 / 5
$186 avg/night
2 beds
1 Bathroom
Guests 5
3 reviews
Cozy Beach Cottage Just Minutes Walk From South Beach, Private...
Guests5
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$71 avg/night
2 beds
1 Bathroom
Guests 5
9 reviews
Home Sweet Home - Long Island, ME
Guests6
Bedrooms3
Bathroom1
Wonderful 5 / 5
$285 avg/night
3 beds
1 Bathroom
Guests 6
1 reviews
Private Waterfront Cottage - watch the sunset over the water every...
Guests6
Bedrooms2
Bathrooms0
Wonderful 4.5 / 5
$147 avg/night
2 beds
0 Bathrooms
Guests 6
6 reviews
Amazing Views from Beachfront Home
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$300 avg/night
3 beds
2 Bathrooms
Guests 6
2 reviews
Home Sweet Home, Long Island ME
Guests6
Bedrooms3
Bathroom1
Wonderful 0 / 5
$200 avg/night
3 beds
1 Bathroom
Guests 6
Beautiful Island Home With Oceanfront Views
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$271 avg/night
3 beds
2 Bathrooms
Guests 6
5 reviews
Beautiful Island Retreat off the Coast of Maine
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.5 / 5
$414 avg/night
3 beds
2 Bathrooms
Guests 6
2 reviews
Book now, summer 2018! 2 BR, 2 Bath Furnished Condo, 1 mile from...
Guests5
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$81 avg/night
2 beds
2 Bathrooms
Guests 5
20 Second Walk to Willard Beach!
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$165 avg/night
2 beds
2 Bathrooms
Guests 5
21 reviews
Sophisticated Downtown Condo - Inquire For Special July Offer!
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$67 avg/night
2 beds
1 Bathroom
Guests 6
24 reviews
Oceanfront - Luxury 3BR Condo Sleeps 8 to 12 - End Unit - Own...
Guests12
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$157 avg/night
3 beds
2 Bathrooms
Guests 12
6 reviews
Large Cozy Home In Quiet Neighborhood
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.6 / 5
$157 avg/night
4 beds
2 Bathrooms
Guests 8
7 reviews
Luxury One Bedroom, 1 bath
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$65 avg/night
1 bed
1 Bathroom
Guests 2
4 reviews
The Birdhouse at Willard Beach ~ a Maine cottage at the beach
Guests5
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$170 avg/night
3 beds
1 Bathroom
Guests 5
88 reviews
Quiet, Cozy, Sleep Great. Yard+Deck. Great Value. Family-Friendly.
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$85 avg/night
2 beds
1 Bathroom
Guests 5
50 reviews
Adorable, light-filled bungalow near beaches and downtown - pet ok!
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$165 avg/night
2 beds
2 Bathrooms
Guests 4
100 reviews
Incomprable Ocean View
Guests6
Bedrooms2
Bathroom1
Wonderful 4.7 / 5
$30 avg/night
2 beds
1 Bathroom
Guests 6
27 reviews
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean...
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$256 avg/night
3 beds
2 Bathrooms
Guests 6
37 reviews
Custom Old Port Penthouse w/Breathtaking Views + Your Own Cupola...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$308 avg/night
2 beds
2 Bathrooms
Guests 4
49 reviews
'Cozy' Retreat at the Water's Edge
Guests2
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$128 avg/night
1 bed
1 Bathroom
Guests 2
40 reviews
Newly Renovated Craftsman Home Walking Distance To Willard Beach!
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$197 avg/night
3 beds
2 Bathrooms
Guests 8
40 reviews
Beautiful & Charming Vacation Retreat
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$65 avg/night
3 beds
2 Bathrooms
Guests 10
14 reviews
Atlantic Ocean Views, Private Beach. Newly Built Home Close To...
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$298 avg/night
3 beds
3 Bathrooms
Guests 8
18 reviews
Five minute walk to Willard Beach, sleeps six!
Guests6
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$300 avg/night
3 beds
1 Bathroom
Guests 6
19 reviews
'Lofty' Waterfront Camp 'The Best Kept Secret in Harpswell!'
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$175 avg/night
2 beds
1 Bathroom
Guests 6
45 reviews
Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of...
Guests6
Bedrooms2
Bathroom1
Wonderful 5 / 5
$225 avg/night
2 beds
1 Bathroom
Guests 6
29 reviews
Gorgeous Two Story, 2 Bedroom, Pet & Baby Friendly, 2 min. Walk...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$175 avg/night
2 beds
1 Bathroom
Guests 4
44 reviews
sleeps 10 ocean views, steps to beautiful Higgins Beach
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$275 avg/night
4 beds
2 Bathrooms
Guests 10
38 reviews
Gorgeous Two Story, Two Bedroom, Pet and Baby Friendly, Close To...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$185 avg/night
2 beds
1 Bathroom
Guests 4
22 reviews
Charming Victorian Studio in Portland's Art District
Guests2
Studio
Bathroom1
Wonderful 5 / 5
$160 avg/night
Studio
1 Bathroom
Guests 2
88 reviews
Breathtaking Ocean Views | Victorian Terrace on the Prom | Great...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.7 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 4
12 reviews
Wonderfully Located One Bedroom Executive Condo, Walk Everywhere!
Guests2
Bedroom1
Bathroom1
Wonderful 4.6 / 5
$221 avg/night
1 bed
1 Bathroom
Guests 2
29 reviews
Oceanfront Victorian Cottage
Guests8
Bedrooms3
Bathrooms0
Wonderful 4.5 / 5
$149 avg/night
3 beds
0 Bathrooms
Guests 8
10 reviews
Stunning Victorian Townhouse in the heart of Portland's West End
Guests10
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$399 avg/night
4 beds
3 Bathrooms
Guests 10
24 reviews
Beautiful Cottage style 2BR house, close to beach, fenced in yard...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$181 avg/night
2 beds
1 Bathroom
Guests 4
31 reviews
Beachfront Condo with Sweeping Ocean Views
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$67 avg/night
3 beds
2 Bathrooms
Guests 6
2 reviews
Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco...
Guests10
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$455 avg/night
5 beds
3 Bathrooms
Guests 10
45 reviews
NEW: Perfect Location in the Old Port w/ Beautiful Views & Access...
Guests5
Bedroom1
Bathroom1
Wonderful 4.5 / 5
$150 avg/night
1 bed
1 Bathroom
Guests 5
22 reviews
Maine Oceanfront Home -- Year-Round Rental!
Guests11
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$311 avg/night
4 beds
2 Bathrooms
Guests 11
56 reviews
DON'T MISS OUT/ SEPT SPECIALS/GRAND VICTORIAN / HOT TUB
Guests7
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$237 avg/night
2 beds
2 Bathrooms
Guests 7
10 reviews
Your very own idyllic panoramic view, lobster boats, kayaking...
Guests6
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$60 avg/night
3 beds
1 Bathroom
Guests 6
17 reviews
Private Pet-Friendly and Kid-Friendly Apartment in 1780's Maine...
Guests3
Bedroom1
Bathroom1
Wonderful 5 / 5
$94 avg/night
1 bed
1 Bathroom
Guests 3
5 reviews
Steps from Willard Beach with Ocean Views.
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$138 avg/night
1 bed
1 Bathroom
Guests 2
19 reviews
Casco Bay-Eastern Prom,Ocean Views
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$200 avg/night
1 bed
1 Bathroom
Guests 2
42 reviews
Charming Peaks Island Cottage
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$122 avg/night
1 bed
1 Bathroom
Guests 4
19 reviews
GORGEOUS! OCEAN VIEWS! 2 MINUTE WALK TO BEACH.YEAR ROUND. CLOSE TO...
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$156 avg/night
1 bed
1 Bathroom
Guests 4
51 reviews
Cozy Artistic Brick Bungalow, Close to Beach, Pet friendly
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$181 avg/night
1 bed
1 Bathroom
Guests 4
27 reviews
3 Bedroom House With Large Fenced In Backyard
Guests7
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$171 avg/night
3 beds
2 Bathrooms
Guests 7
7 reviews
Cozy cottage on the water not far from Freeport shopping and...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 6
16 reviews

Long Island, ME, USA Vacation Rentals

Cozy Cottage Near Fowler's Beach

Cozy Beach Cottage Just Minutes Walk From South Beach, Private...

Home Sweet Home - Long Island, ME

Private Waterfront Cottage - watch the sunset over the water every...

Amazing Views from Beachfront Home

Home Sweet Home, Long Island ME

Beautiful Island Home With Oceanfront Views

Beautiful Island Retreat off the Coast of Maine

Book now, summer 2018! 2 BR, 2 Bath Furnished Condo, 1 mile from...

20 Second Walk to Willard Beach!

Sophisticated Downtown Condo - Inquire For Special July Offer!

Oceanfront - Luxury 3BR Condo Sleeps 8 to 12 - End Unit - Own...

Large Cozy Home In Quiet Neighborhood

Luxury One Bedroom, 1 bath

The Birdhouse at Willard Beach ~ a Maine cottage at the beach

Quiet, Cozy, Sleep Great. Yard+Deck. Great Value. Family-Friendly.

Adorable, light-filled bungalow near beaches and downtown - pet ok!

Incomprable Ocean View

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean...

Custom Old Port Penthouse w/Breathtaking Views + Your Own Cupola...

'Cozy' Retreat at the Water's Edge

Newly Renovated Craftsman Home Walking Distance To Willard Beach!

Beautiful & Charming Vacation Retreat

Atlantic Ocean Views, Private Beach. Newly Built Home Close To...

Five minute walk to Willard Beach, sleeps six!

'Lofty' Waterfront Camp 'The Best Kept Secret in Harpswell!'

Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of...

Gorgeous Two Story, 2 Bedroom, Pet & Baby Friendly, 2 min. Walk...

sleeps 10 ocean views, steps to beautiful Higgins Beach

Gorgeous Two Story, Two Bedroom, Pet and Baby Friendly, Close To...

Charming Victorian Studio in Portland's Art District

Breathtaking Ocean Views | Victorian Terrace on the Prom | Great...

Wonderfully Located One Bedroom Executive Condo, Walk Everywhere!

Oceanfront Victorian Cottage

Stunning Victorian Townhouse in the heart of Portland's West End

Beautiful Cottage style 2BR house, close to beach, fenced in yard...

Beachfront Condo with Sweeping Ocean Views

Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco...

NEW: Perfect Location in the Old Port w/ Beautiful Views & Access...

Maine Oceanfront Home -- Year-Round Rental!

DON'T MISS OUT/ SEPT SPECIALS/GRAND VICTORIAN / HOT TUB

Your very own idyllic panoramic view, lobster boats, kayaking...

Private Pet-Friendly and Kid-Friendly Apartment in 1780's Maine...

Steps from Willard Beach with Ocean Views.

Casco Bay-Eastern Prom,Ocean Views

Charming Peaks Island Cottage

GORGEOUS! OCEAN VIEWS! 2 MINUTE WALK TO BEACH.YEAR ROUND. CLOSE TO...

Cozy Artistic Brick Bungalow, Close to Beach, Pet friendly

3 Bedroom House With Large Fenced In Backyard

Cozy cottage on the water not far from Freeport shopping and...