Long Island holiday rentals

We found 569 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Long Island that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a TV. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Long Island

Showing deals for:18 Dec - 25 Dec

Kitchen recently renovated.
Property grounds
Floors recently refinished.
Open floor plan.
Wonderful
(41 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
AU$5,224
for 7 nights, 1 home
AU$746 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Dining
Willard Beach
Back yard
Master bedroom with queen bed and ceiling fan
Exceptional
(72 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
AU$4,386
for 7 nights, 1 home
AU$627 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Private kitchen
Interior
Pool
Terrace/patio
Exceptional
(17 reviews)

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough

8% off
AU$5,599
for 7 nights, 1 home
AU$800 per night
includes taxes & fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Interior
Outdoor dining
Private kitchen
The living room leads out to a private deck with a dining table that seats 4.
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
AU$3,923
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
picnic area
Casco Bay
WELCOME
Kitchen
Exceptional
(102 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,927
for 7 nights, 1 apartment
AU$418 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
View from living room
Terrace/patio
Private kitchen
Room
Exceptional
(190 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
AU$2,172
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Private kitchen
Marina
Living area
Dining
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
AU$2,553
for 7 nights, 1 apartment
AU$365 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Private kitchen
Living area
Private kitchen
Dining
Exceptional
(134 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

12% off
AU$2,943
for 7 nights, 1 apartment
AU$420 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
View from inside unit.
Large open concept living space with tall sloped celling and a loft.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Exceptional
(8 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,898
for 7 nights, 1 apartment
AU$557 per night
includes taxes & fees
Exchange Street Skylight Loft
Off-street parking behind building dedicated to this unit only.
Living area
Room
Interior
Exceptional
(42 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,688
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Private kitchen
Dining
Living area
Outdoor dining
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

8% off
AU$2,713
for 7 nights, 1 apartment
AU$388 per night
includes taxes & fees
Fall In Love With Portland!
Interior
Living area
Private kitchen
Dining
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,203
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Walnut topped kitchenette counter with coffee maker.
Interior
Room
Interior
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,210
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Living area
Interior
Exterior detail
Living area
Exceptional
(101 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
AU$2,841
for 7 nights, 1 apartment
AU$406 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Scales! The best spot in town for a delish dinner.
Tour the Victorian Mansion at the bottom of the street.
Interior
Living area
Exceptional
(65 reviews)

Historic Home in the West End. Private Parking.

Portland

8% off
AU$2,526
for 7 nights, 1 apartment
AU$361 per night
includes taxes & fees
Historic Home in the West End. Private Parking.
Private kitchen
Smalls! A short walk from the house.
Room
Pia Men Miyake, the best place for lunch!
Exceptional
(23 reviews)

West End Bright Spot with Parking.

Portland

8% off
AU$2,043
for 7 nights, 1 apartment
AU$292 per night
includes taxes & fees
West End Bright Spot with Parking.
Large, well-stocked Kitchen w/stainless steel counter and appliances
5 min car ride to Downtown/Old Port.
Large deck with seating for six, festive lighting and a firepit. Views and sun!
Festive lighting at your control.
Exceptional
(132 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

8% off
AU$3,002
for 7 nights, 1 apartment
AU$429 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Room
Private kitchen
Outdoor dining
Dining
Exceptional
(14 reviews)

Harborview - Curated East End Escape w/ Parking

Portland

8% off
AU$7,269
for 7 nights, 1 apartment
AU$1,038 per night
includes taxes & fees
Harborview - Curated East End Escape w/ Parking
Living area
Interior
Dining
Exterior detail
Exceptional
(21 reviews)

New England Charm, Portland - Parking included

Portland

8% off
AU$4,273
for 7 nights, 1 apartment
AU$610 per night
includes taxes & fees
New England Charm, Portland - Parking included
Living area
Interior
Interior
Dining
Exceptional
(22 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,428
for 7 nights, 1 apartment
AU$633 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
Room
Scales in the Old Port for the best seafood
Interior
The State Theater is a 5 minute walk away.
Exceptional
(55 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
AU$2,711
for 7 nights, 1 apartment
AU$387 per night
includes taxes & fees
Charming West End Hideaway. Private Parking

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Charming Long Island will entice you

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Long Island. This romantic city attracts visitors thanks to its restaurants and shopping. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Long Island

Are you hoping to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Long Island a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Aquaboggan Water Park (15 mi / 24.1 km)
  • Pirate's Cove (15.8 mi / 25.4 km)
  • Dunegrass Golf Club (15.7 mi / 25.3 km)
  • Gilsland Farm Audubon Center (3.8 mi / 6.1 km)
  • Riverside Municipal Golf Course (7.3 mi / 11.7 km)
  • Happy Wheels Skate Center (8.1 mi / 13 km)

Exploring the natural features in Long Island

Whether you're an active traveller or just want to spend some time taking in the scenery, Long Island is a great place to spend some time outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Sand Beach (2.5 mi / 3.9 km)
  • East End Beach (3.6 mi / 5.8 km)
  • Eastern Promenade (3.7 mi / 6 km)
  • Willard Beach (3.9 mi / 6.3 km)
  • Thompson's Point (6.5 mi / 10.4 km)
  • Casco Bay (8.8 mi / 14.2 km)

How to get to and around Long Island

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 7.4 mi (11.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 25.9 mi (41.6 km) away.

Frequently asked questions

What is the best area to stay in Long Island when booking a holiday rental?
When looking for the best area to stay in Long Island, Maine, you might consider the charming neighbourhoods that offer both tranquillity and access to local attractions. One delightful option is the area near the ferry terminal, which provides easy access to the island and is close to beautiful waterfront views. This area typically features a range of holiday rentals, from cosy cottages to spacious homes, making it an ideal choice for families or groups.In this vicinity, you can enjoy the stunning landscapes and the picturesque beaches, superb for sunbathing or leisurely strolls. One of the highlights is the local lighthouse, which offers not only a glimpse into the island's maritime history but also stunning views of the surrounding waters. Additionally, the nearby walking trails are a favourite among visitors, as they provide a wonderful opportunity to explore the island's natural beauty.Another lovely area to consider is near the local shops and eateries, where you can immerse yourself in the island's community spirit. This location is convenient for sampling fresh seafood and local delicacies. The range of properties here often reflects the island's unique charm, with many rentals featuring rustic designs and modern amenities.
Where are the best areas for renting a beach house in Long Island?
For renting a beach house in Long Island, Maine, the areas along the southern coast are particularly appealing. The region near the ferry terminal offers convenient access to sandy beaches and a charming seaside atmosphere. Here, visitors can find a variety of coastal cottages and homes, many featuring amenities such as outdoor decks for dining al fresco, spacious living areas, and fully equipped kitchens ideal for family gatherings. Some properties also include private beach access, making it easy to enjoy the sun and sea right at your doorstep.Moving further along the coast towards the village area, you'll discover quaint beach houses located among the trees, providing a more secluded experience. These homes often come with additional features like outdoor showers, fire pits for evening gatherings, and expansive yard spaces superb for children to play. The proximity to local shops and eateries enhances the convenience for travellers, allowing for easy access to fresh seafood and local produce.Additionally, the scenic beauty of the surrounding landscapes offers opportunities for outdoor activities, including kayaking and hiking along the coastline. Rentals in this area cater to both relaxation and adventure, allowing guests to immerse themselves in the natural beauty of Long Island while enjoying comfortable and well-equipped accommodations.
What is the most popular type of holiday rental accomodation in Long Island?
In Long Island, holiday houses are the most popular type of holiday rental, with around 20 available throughout the area. These houses typically offer spacious interiors with multiple bedrooms, fully equipped kitchens, and comfortable living and dining areas, making them ideal for families or groups looking for a home away from home. Additionally, there are several charming cottages that provide a more quaint and cozy atmosphere, often featuring lovely outdoor spaces where guests can relax and enjoy the scenic surroundings.
Are there any family house rentals in Long Island?
In Long Island, Maine, there are several family-friendly house rentals available, making it a delightful destination for those travelling with children. The island offers a range of homes, many of which are situated near the picturesque coastline and provide easy access to sandy beaches and scenic walking trails.Properties often feature spacious living areas, equipped kitchens for preparing family meals, and outdoor spaces superb for kids to play or for family gatherings. Many accommodations also come with amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay for visitors.Moreover, the charming community atmosphere of Long Island is complemented by nearby points of interest, like the local lighthouse and quaint shops.
Are there pet-friendly house rentals in Long Island?
In Long Island, Maine, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. The island offers charming cottages and larger homes that often come equipped with amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, making them ideal for family getaways or group retreats. Many properties feature lovely views of the surrounding waters, as well as easy access to the beach.The island is known for its tranquil atmosphere and natural beauty, great for pet owners who enjoy outdoor activities. Nearby, there are scenic walking trails and beaches where pets can roam freely, allowing for enjoyable days spent exploring the picturesque coastline.
Are there any remote work holiday rentals in Long Island?
In Long Island, Maine, there are approximately 20 remote work holiday rentals available, making it a suitable option for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, such as high-speed Wi-Fi and dedicated workspaces, ensuring a productive environment. Additionally, some rentals feature printers and safe storage for important documents, catering specifically to the needs of remote workers.The island's tranquil setting, with its stunning coastal views and proximity to nature, provides an ideal backdrop for both work and relaxation. Travellers can expect comfortable accommodations with well-equipped kitchens for meal preparation, as well as inviting living areas to unwind after a day of work. Furthermore, the nearby beaches and scenic walking trails offer an opportunity to recharge during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Long Island?
In Long Island, Maine, popular holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature decks or patios, providing lovely outdoor spaces to relax and enjoy the scenic surroundings. Additionally, some rentals come with a blender for those who enjoy making smoothies or cocktails. A fireplace is often included, great for cosy evenings after a day of exploring the island. Onsite parking is another convenient amenity, making it easier for guests to navigate the area.
When is the best time to visit Long Island for a holiday rental?
The peak time to visit Long Island, Maine, is during the summer months of June to August, with July being the most popular month. This vibrant season draws travellers, eager to bask in the warm sunshine while enjoying outdoor activities like kayaking, hiking, and exploring the stunning coastline. The long, sunlit days are superb for beach outings and local festivals, creating a lively option on the island.During this peak season, temperatures typically range from 20 to 30 degrees Celsius, offering a comfortable climate for both relaxation and exploration. Visitors can indulge in fresh seafood dining, stroll through charming coastal towns, and soak in the picturesque views of the Atlantic Ocean.For those looking for a more budget-friendly option, consider visiting Long Island in November. This time of year offers a quieter experience, superb for enjoying tranquil walks along the beach and experiencing the island's natural beauty without the summer crowds. The crisp autumn air and stunning fall foliage create a picturesque backdrop for a peaceful getaway.
What are the top attractions in Long Island?
In Long Island, Maine, visitors can enjoy a serene atmosphere and a variety of attractions. The island is known for its beautiful coastal scenery and outdoor activities. The picturesque beaches, such as the one at Long Island's southern shore, are great for sunbathing and swimming during the warmer months.For those interested in history, the Long Island Historical Society offers insights into the local heritage, while the nearby lighthouse provides a charming backdrop and a lovely spot for photography. Nature enthusiasts can explore the island's walking trails, which wind through lush landscapes and offer stunning views of the surrounding waters.
Are all fees included in the Long Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Long Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Long Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Long Island holiday homes?
You can find great discounts on holiday homes in Long Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Long Island holiday home booking on Stayz?
To find Long Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Long Island?
A long-stay holiday home in Long Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Long Island holiday home?
Book your Long Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Long Island?
Prices for holiday homes in Long Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Long Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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