Long Island holiday lettings

We found 546 holiday rentals — enter your dates for availability

Discover a selection of 7 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:15 May - 22 May

Image gallery for Charming, Secluded, Island Getaway!

Be Chill Cottage on Peaks Island
10 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)

Charming, Secluded, Island Getaway!

Portland

12% off
Price is £1,565
for 7 nights, 1 home
£224 per night
includes taxes & fees
Charming, Secluded, Island Getaway!

Find spaces that suit your style

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Why visit Long Island

  • Pristine Beaches: Long Island boasts beautiful beaches, perfect for sunbathing and relaxation.
  • Historic Lighthouses: Explore charming lighthouses that reflect the island's maritime heritage.
  • Scenic Accommodations: Enjoy a range of holiday rentals, from quaint cottages to modern condos.
  • Welcoming Community: Experience the warmth of friendly locals and the rich local culture.
  • Outdoor Activities: Engage in various outdoor pursuits, ideal for families and solo adventurers alike.

Popular types of accommodation in Long Island

Planning a getaway to Long Island? The excitement begins with selecting the perfect accommodation. Discover a variety of holiday rentals, from charming cottages and spacious houses to modern condos. Whether you're seeking a tranquil retreat or a vibrant stay by the beach, Long Island offers an array of holiday lettings to suit every traveller's needs. Explore your options for unforgettable holiday homes and enjoy a delightful escape.

  • Houses: The top choice for visitors to Long Island, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: These delightful, quaint dwellings provide a charming atmosphere for a peaceful getaway.
  • Condos: A practical option that combines modern amenities with convenient locations, perfect for short or extended stays.
  • Apartments: Offering flexibility and independence, these rentals are suitable for couples and solo travellers alike.
  • Cabins: Embrace the great outdoors with a rustic cabin retreat, perfect for those seeking nature and tranquillity.**

Top attractions near Long Island

Long Island, Maine, offers a delightful escape for those keen on outdoor activities and scenic beach holidays. Visitors can explore beautiful beaches, historic lighthouses, and charming houses that reflect the local culture. Ideal for sightseeing, this destination caters to travellers seeking a blend of culture and outdoor experiences. Whether you're with family or exploring solo, Long Island promises a relaxing yet enriching holiday experience.

  • Portland Head Light: A historic lighthouse steeped in maritime culture, the Portland Head Light offers stunning coastal views and a glimpse into the region's rich nautical history. Located 3.1km from Long Island, it's a perfect spot for photography and exploration.
  • East End Beach: Just 2.5km away from Long Island, East End Beach is a picturesque stretch of sand ideal for sunbathing, swimming, and relaxing by the Atlantic. The beach vibes create a serene atmosphere for families and visitors alike.
  • Cross Insurance Arena: This entertainment hub, located 3.1km from Long Island, hosts a variety of events including concerts and sports. The arena is perfect for family outings and enjoying lively performances in a vibrant atmosphere.

Things to do recommended for couples

For a romantic getaway on Long Island, enjoy a concert at Thompson's Point, indulge in luxury at the Portland Club, or embark on an adventurous day with water sports at Capt Lyman Stuart. Each experience offers a unique charm perfect for couples seeking unforgettable moments.

Things to do recommended for families

Families visiting Long Island, Maine, can enjoy a thrilling game at Hadlock Field, explore the stars at Portland Observatory, and unwind at Fort Williams Park, perfect for relaxation and wellness. These attractions offer a delightful mix of sports, entertainment, and outdoor fun for all ages.

Things to do recommended for groups

Explore the Maine Mall for a lively shopping experience, only 5.6km from Long Island. Enjoy a visit to the Lyric Music Theater, just 2.5km away, for a touch of culture and entertainment. Don’t miss the iconic LL Bean Flagship Store, located 7.5km from your base.

What do I need to keep in mind when booking a vacation in 'Long Island

If you’re travelling with a group, family, pets, or planning an extended stay, it’s essential to apply the appropriate filters to suit your needs. Here are some helpful tips for booking with Vrbo.

  • Traveling to Long Island with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group activities. Thankfully, you can refine your search to include all these options and more on Vrbo.
  • Traveling to Long Island with young kids: Journeying with young children can be quite demanding. It's important to prioritise their comfort and safety, alongside ensuring there are suitable amenities for their age, such as a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Long Island: For many, a family holiday feels incomplete without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Long Island: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Long Island

Long Island, Maine, offers a delightful blend of tranquil beaches and stunning natural scenery, perfect for a relaxing getaway. Whether you're seeking family-friendly activities, a romantic escape, or a business retreat, the vibrant atmosphere caters to all. Explore charming nearby neighbourhoods, indulge in holiday rentals, or unwind in picturesque villas overlooking Long Island Sound. With friendly locals and a rich culture, your visit promises unforgettable experiences amidst breathtaking coastal beauty.

  • Portland: Located a mere 2.5km from Long Island, Portland is a vibrant city known for its stunning outdoor spaces and family-friendly activities. Visitors can enjoy a variety of experiences, from exploring local theatres to indulging in shopping at the lively mall centre. The city's proximity to beautiful beaches and serene lakes makes it perfect for a day out in nature. Don't miss the chance to stroll along the waterfront, where the scenic views are simply breathtaking.
  • South Portland: Just 3.1km away from Long Island, South Portland offers a delightful mix of family-oriented and urban experiences. The city is home to key shopping centres and educational facilities, catering to both tourists and locals. With its inviting beaches and peaceful lakes, South Portland is ideal for a relaxing day spent with loved ones. Be sure to explore the vibrant local eateries and shops that contribute to the city's unique charm.
  • Peaks Island: Only 1.2km from Long Island, Peaks Island is a picturesque getaway that enchants visitors with its natural beauty and romantic atmosphere. This idyllic island is perfect for outdoor enthusiasts, offering recreational areas and scenic spots for relaxation. Explore the local history museum to learn about the island’s past, or unwind on its tranquil beaches. Peaks Island is a must-visit for anyone looking to escape the hustle and bustle of city life.

Best time to go to Long Island

If you're planning a trip to Long Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.6°F (-3.0°C)Light RainMostly SunnyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostly SunnyAverageSlightly Low
March33.8°F (1.0°C)Light RainMostly SunnyAverageSlightly Low
April43.7°F (6.5°C)Light RainMostly SunnyAverageAverage
May53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
June61.3°F (16.3°C)Light RainMostly SunnyHighSlightly High
July68.2°F (20.1°C)Light RainMostly SunnyHighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
September61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
October52.3°F (11.3°C)Light RainMostly SunnyLowAverage
November41.7°F (5.4°C)Light RainMostly SunnyLowAverage
December33.4°F (0.8°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, booking a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last paused, or manage your travel arrangements. You can easily find properties you've previously saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards feature, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Dunegrass Golf Club (15.7 mi / 25.3 km)
  • Pirate's Cove (15.8 mi / 25.4 km)
  • Land's End Gift Shop (8.8 mi / 14.1 km)
  • Aquaboggan Water Park (15 mi / 24.1 km)
  • Gilsland Farm Audubon Center (3.8 mi / 6.1 km)
  • Riverside Municipal Golf Course (7.3 mi / 11.7 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.
How much does it cost to rent a holiday home in Long Island?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Long Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Long Island holiday house rentals?
You can find great discounts on house rentals in Long Island on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Long Island?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Long Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Long Island holiday rental?
Book your Long Island holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Long Island home rental booking on Vrbo?
To find Long Island holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Long Island holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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